Nanotube Functionalization: History
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Contributor:
Marianna V. Kharlamova
,
Maksim Paukov
,
Maria G. Burdanova
The carbon nanotubes (CNTs) are modified by different routes, such as covalent and non-covalent modification of the outer surface, the substitution of atoms or the filling of CNT channels. Covalent functionalization (adsorption) requires reactive species that can form covalent adducts with the sp2 carbon of CNT. The main advantage of the covalent functionalization of CNTs is that it is stronger than non-covalent interactions, however, it requires damage to the sidewalls. Unlike non-covalent functionalization, it changes the electronic structure, resulting in the irreversible loss of double bonds. These changes can affect conductivity properties and therefore, some applications.
  • carbon nanotubes
  • covalent modification
  • non-covalent modification

1. Introduction

Surface modifications of SWCNTs are not only achievable by covalent functionalization, but also by non-covalent methods. Known examples of molecules spontaneously assembling into micelles around SWCNTs are polymers [1], polycyclic aromatic compounds [2][3][4][5][6], biological species [7] and surfactants [8][9][10].
Covalent incorporation of foreign atoms within the CNT lattice is proposed for the effective engineering of CNT properties by consequent doping. Numerous materials have been used for SWCNTs’ substitution, such as N, B, P, Si, Cl or Ar. The important parameter in this case is the controlled concentration of the embedded atoms. Substitutional doping introduces strongly localized electronic features in the valence or conduction bands of CNTs, which makes it different from doping. Different methods can be utilized for the substitution of atoms: arc-discharge, laser-ablation, CVD, chemical reactions and plasma treatment [11].

2. Functionalization

Defect functionalization is based on the attachment of the desired functional group to the existing or intentionally created defects on the CNT. In reality, CNTs are not ideal nanostructures but rather contain 1-3 % of defects naturally occur during the synthesis. Another type of defect can be invariably introduced during the preparation and purification stages. Ultrasonic treatment and shear mixing, widely used to disperse CNTs in solution, can introduce the defects. The effect of sonication is based on the cavitation effect that is able to break the CNT aggregates (bundles) in addition to the shear force effect. This causes the formation of the structural defects, eventually their breakage. After defect introduction the sidewalls are expected to be chemically active improving the reactivity of CNT.

Oxygenated sites can also to be considered as defects. Chemical oxidation of nanotubes is mainly achieved by using either wet chemistry or gaseous oxidants. One way of creating defects and functional groups is an oxidative damage to the nanotube framework by strong acids or oxidants, such as HNO3, H2SO4, KMnO4 which leave holes functionalized with oxygenated functional groups as well as open CNT’s caps caps [12][13][14]. The oxidation can be also archived by using hydrochloric acid [15][16], hydrogen peroxide [17], potassium permanganate [18], oxidative persulfates [18], hypochlorites [19]. In Ref. [53] it was shown that the oxidation of CNTs with concentrated HNO3 results in the defect formation in addition to the opening the ends of nanotubes. Besides that, it stimulates the formation of the aromatic polycyclic compounds, fulvic acids on the surface, which can be removed by alkali and then reversibly reabsorbed. This consequently results in the improving dispersion of CNTs in the aqueous solution.

The gas-phase functionalization of CNTs, including oxidation, has been carried out. Here, carbon dioxide [20][21], water vapor [22], air, oxygen [23][24][25], ozone [26][27][28], used as oxidants. Water vapor is effective as an oxidizing reagent only when it is introduced into the reaction during CVD synthesis of CNTs [22]. It was shown that in this method nanotubes are produced with a sufficiently large number of defects and oxygen content up to 42 wt. % in different functional groups. So far, the oxidation with oxygen in air is the most effective way of oxidation as it proceeds with the simultaneous CNT’s cleaning, shorting and opening. In general oxidation treatment leads the p-type doping of CNTs shifting the Fermi level towards valence band.

Moreover, some functionalization methods are combined together. For example, in [29], the effectiveness of the same carboxylation of CNTs in a mixture of nitrogen-nitric acid (3:1) is accompanied by cavitation caused by the ultrasonic action at room temperature. In addition, the hydrogen peroxide effectiveness in oxidation of CNTs increases with UV irradiation [30][31]. Air can be used for additional oxidization of CNTs pretreated with acids [32].

It was also shown that the oxidation processes strongly depends on the curvature of the CNT’s wall and consequently to the diameter dependence [33][34][35]. Upon oxidative functionalization of CNTs, the affinity of their surfaces to various solvents and polymer matrices increases. The defects on CNTs created by oxidants are stabilized by bonding with carboxylic acid (–COOH) or hydroxyl (–OH) groups, ketone, alcohol and ester groups formation. These groups can be used for precursors for further functionalization: silanization [36][37][38], esterification [39][40][41], thiolation, alkylation and arylation, biomolecules and polymer attachment.

CNT silanization is the interaction of oxidized CNTs with organosilanes. The silanization after oxidation usually takes place in a few steps. Firstly, the hydrolysis of silanes into silanols is performed. The creation of hydrogen bonds between oligomers and the surface hydroxyl groups of carbon nanofillers as well as the condensation of silanols into oligomers occur in the next phase. Finally, Si-O-C bonds are created by the interaction of Si-OH groups with OH groups on CNTs. The 3-aminopropyltriethoxysi-lane has been widely used as a silane agent [42][43][44][45][46]. Lin et al. used comparable techniques to attach both polyethylene glycol and iron oxide in-silica nanoparticles to the surface of CNTs [47].

Access to numerous CNT surface functionalizations is made possible by adding carboxylic and hydroxyl groups to CNTs. CNTs can be functionalized via esterification or amidation. Typically, carboxylic groups are activated to acyl chlorides by thionyl chloride, and then amidation and esterification reactions convert them to carboxamides (or carboxyesters) to introduce a variety of functional groups as nucleophiles, such as aliphatic or aryl amines, amino acid derivatives, ensims, peptides, or amino-group substituted dendrimers. Thiolation with sodium sulfite, sodium hydroxide, and carboxylation with thionyl chloride are used to attach a similar thiol group [48]. The presence of carboxil groups themselves leads to the reduction of van der Waals interactions between CNT which results in effective debundeling and separation into individual but shortened nanotubes.

The chemical manipulation of carbon nanotubes sidewall by fluorination and then defluorination is well developed [49][50][51]. It can be carried out efficiently in the presence of F2 at temperatures between 150 and 400 °C [52]. The interest is that the fluorine atoms can then be substituted by alkyl groups or by amines. Fluorinated CNTs are widely used for a wide range of chemical functionalization. For example, side-wall alkylation and arynation of fluorinated SWCNTs was performed using alkyllitium species, including methyl, ethyl, butyl, hexyl, octyl, dodecyl. Amino groups can be also attached to the sidewalls of fluorinated CNTs [53]. These materials exhibit an excellent reinforcement effect in epoxy-based systems which results in improved properties as mechanical robustness. The chlorination and bromination are another two methods that has been used for SWCNT functionalization. Chlorine applied in the functionalization of CNTs can be liquid precursors as thionyl chloride, chloroform, trichloromethane, tetrachloroethylene, or hydrochloric acid or solid precursors as dichlorocarbene or chlorine gaseous precursors [54][55][56][57]. Purified CNT sample attached 1.8 at.% of bromine after two days in saturated bromine vapors at room temperature [58][59].

The most common approach for hydrogenation is a wet chemistry which includes the dispersion of a mixture of lithium and CNT in diaminoethane [60]. The protonation of reduced lithium also reduce CNT with methanol leading to the formation of hydrogenated SWCNTs [61]. As the result the covalently bonded CH derivatives are formed. High-boiling polyomides also was used as hydrogenation reagent for CNTs [62]. At room temperature, it has been demonstrated that hydrogenated SWNTs with covalent C-H bonds constitute a stable hydrogen storage [63][64][65].

CNTs functionalized with fluorescein or a fluorescent bioactive peptide can also effectively cross the cell membrane without the significant damage of the membrane [66][67]. For therapeutic biomolecules, such as proteins, peptides, deoxyribonucleic acid (DNA), and siRNA, covalent functionalization has been widely reported [68]. For example, CNTs were used to deliver streptavidin into the cell [69]. It has been demonstrated that SWNTs may be covalently functionalized to peptide nucleic acid (PNA), an analog of uncharged DNA, and then hybridized to molecular wires containing complementary DNA [70]. There have been several reports of bovine serum albumin protein molecules adhering to f-MWCNTs in an aqueous buffer solution [71]. CNTs can introduce a DNA molecule into the cell nucleus which opens an opportunity to use CNTs in gen-delivery [72]. CNT, after covalent functionalization, can be used to carry peptide antigens [73]. Recently, the translocation of the RNA using non-functionalized SWCNT into breast cancer cells has also been reported [74].

In general, the CNTs covalently-functionalized are soluble in many organic solvents due to the attachment of polar or non-polar groups. The main difficulty in developing covalent functionalization [71] arise from the conversion sp2 into sp3 hybridization. This consequently lead to changes in mechanical, optical and electrical properties. From the other hand, the CNTs functionalized covalently open the road to many application which require the change in the optical and electrical properties [75][76].

The first commonly used non-covalent functionalization is surfactant based. These types of molecules results in the dispersion of the CNTs via physical adsorption. Both ionic and non-ionic surfactants have been used. The known surface charge of CNTs can be used to predict colloidal stability of CNT solutions and interaction (adsorption) mechanism with ionic surfactants.. A larger negative surface charge and steric repulsion, for instance, are produced when CNTs and SDS interact through the hydrophobic components, which increases the stability of the dispersion. Therefore, the purification procedure and tube wall functionalization, which influence its surface charge, may be used to regulate the adsorption mechanism of ionic surfactants [77]. While the polar portion of surfactants interacts with solvent molecules, the hydrophobic (non-polar) portion is often oriented toward the surface of CNTs. The most popular surfactants for dispersing CNTs in an aqueous media are sodium dodecyl sulphate (SDS), sodium dodecyl benzene sulfonate (SDBS), cetyltrimethyl ammonium bromide, Tween, Triton X, and a siloxane polyether copolymer [78][79][80][81][82][83][84]. One of the important parameters for the dispersion of CNTs is CNT to surfactant concentration. For example, a homogeneous dispersion of CNTs was found at the optimum composition of 0.5 wt% CNTs and 2 wt% SDS relative to water. In Ref. [85] found that the surfactant dispersing power follows the order of SDS < Tween 20 < Tween 80 < TX-100. Meanwhile, it was shown that SDBS exhibited superior capability than TX100 and SDS in terms of its capacity to disperse SWCNTs [10]. However, it was reported that the dispersion of MWCNTs in three surfactants followed the order of SDS < CTAB < TX100 [86]. While surfactants are often necessary to utilize individualized SWCNTs in the dispersion, improved surfactant-removing protocols to recover the initial SWCNT properties are needed to ensure optimal performance. The washing with organic solvents [87], acidic oxidation [88], and annealing in inert [87] or oxygen atmospheres are used for this purpose [89].

Through π-π interfaces, aromatic compounds like anthracene, phenanthrene, pentacene, porphyrin, pyrene, and fullerene interact with one another. Under mild sonication, the functional molecule's and large system's strong bonding allows for de-bundling and produces hydrophilicity. CNT@Pyrene hybrid was developed, aiming at improvement in heat transport by the effect of anion addition [90]. Biotin−streptavidin recognition method described in [91]. This complex showed stability in 18 days, and excellent loading capacity (about 1 streptavidin tetramer per 20 nm of SWNT). The anthracene groups were covalently added to the hydroxylated CNTs to aid in orienting the laccase active sites for direct electron transfer between enzymes and electrodes [92]. The excellent electrochemical catalytic property and stability of the functionalized with ferrocene SWCNTs was reported by Yang et al [93]. Huang et al. have used the ferrocene for non-covalent functionalization of SWCNT for L-glutamate detection [94].

The interaction of polymers with CNT surface via wrapping was used to improve the dispersion of CNT in water and organic solvent, and feather enable separation of CNTs by metallicity and chirality, and CNTs from carbonaceous and metal impurities [95][96][97]. The polyvinyl pyrrolidone, polyvinylidene fluoride, polystyrene sulfonate, cellulose derivatives, polypyrroles, glycolipids, and redox polymers was successfully used for CNT dispersion [98].

Dispersions of MWCNT with the pluronic surfactant F-127 were made with the intention of examining the interactions of CNT with biological tissues [99]. A water-soluble globular protein called bovine serum albumin adheres to the surface of CNTs and improves dispersibility [100]. Similar results were shown for MWNT-PEG composites [101].  It was concluded that the functionalizing CNT with PEG enhanced the dispersion of the CNTs and increased their heat capacities [102][103]. On act as a shRNA delivery vehicle, a modified branched polyethylenimine was grafted to carboxylated single-walled carbon nanotubes (SWCNT) using a polyethylene glycol (PEG) linker [104]. CNTs functionalized with DNA were shown to enhance stability used in different applications [105][106][107][108][109]. Similarly to proteins, DNA form tight helices around CNTs, or noncovalent conjugates. DNA-functionalized CNTs were more effective than plain MWCNTs against malignant tissues [109]. Despite the popularity of research on SWCNT-DNA conjugates, only a small number of works has studied the removal of adsorbed DNA on SWCNTs by biological, physical and chemical treatments. Numerous biological and pharmacological uses of chitosan, including drug delivery, cancer treatment, and biosensors, have been researched [110][111][112]. Chitosan could effectively disperse the SWCNTs and provide a suitable biological interface for immobilization of biomolecules [113]. The functionalized CNTs complexed siRNA demonstrated 10–30% silencing activity and 10–60% cytotoxicity [114]. siRNA delivery using CNTs were successfully utilized [115].

Finally, researchers would like to discuss the mechanical interlocking of SWCNT as a possible route for non-covalent functionalization. In particular, in [116] the macrocycle precursors that were terminated with bisalkenes that were wrapped around the NT by ring-closing metathesis were furnished with two-extended tetrathiafulvalene SWNT recognition units.

Nitrogen has one electron more than C, and when it more easily substitutes for C atoms. There are two types of C–N bonds occur: pyridine-type in which each N atom is bonded to two carbon atoms and a type in which N atom is bonded to three carbon atoms. The first type result in either a p- or n-type doping depending on the concentration of N atoms, meanwhile the second type to n-type conducting behavior. In situ doping techniques include high-temperature arc-discharge [117][118], chemical vapor deposition(CVD) [119][120][121][122],chemically solvothermal procedures [123], and laser ablation methods [124][125]. Also N type doping can be archived by various post-treatment methods [126][127]. The post-thermal treating of oxidized CNTs with ammonia was performed [128]. Doping of isolated SWNTs with nitrogen was achieved by mixing appropriate amounts of acetonitrile with xylene. The 2–6 at.% of nitrogen in the SWNTs was observed in controllable manner [129].

The halogens such as fluorine, chloride and bromide can be also attached to the sidewall of CNTs. As it was mentioned in section 1 the fluorination can be effectively used for feather covalent functionalization. The fluorination of CNTs, the formation of so-called fluorotubes, is usually performed by temperature treatment in molecular fluorine environment at 150-600 °C. The precise temperature control results in the control the activity of the substitution, and therefore, in the degree of the fluorination. The heavily doped CNTs was produced and showed increased solubility in alcohols [130]. The comparison between graphene and CNTs fluorination suggested that the curvature resulted in a weakening of the C-F bonding covalence [131]. By diluting fluorine with nitrogen in a ratio of 4:1 and treating SWCNTs with such a mixture at 250°C for 10 h the fluorinaized tubes with the stoichiometry of CF0.43. The heating resulted NTs under He with temperatures ranging from 100 to 400 °C desorb the fluorine[132]. Hydrazine defunctionalizes fluorinated nanotubes, allowing for the recovery of intact CNTs after treatment. Interestingly fluorinated single-walled nanotubes were highly insulating. The fluorination using various synthesis parameters has been studied [133][134].

The alternative commonly used method for CNTs functionalization via substitution is chlorination. Usually, the source of chlorine came from liquid precursors as thionyl chloride, chloroform, trichloromethane, tetrachloroethylene, or hydrochloric acid  or solid as dichlorocarbene or gaseous precursors as Cl2 . The removal of metal catalyst and amorphous carbon residues from CNT has been reported to be accomplished using Cl2 gas and Cl2 aqueous solution treatments. Simultaneously, this protocol introduce chlorine but with a relatively low amount [135]. The chlorine substitution with the concentration of 2.5 atom % on SWCNTs was shown by using electrochemical functionalization in HCl and KCl aqueous solution [136]. A similar concentration (up to 2.9 atom %) of chlorine was introduced by treatment with SOCl2 under high temperature and pressure with prolonged reaction times of up to 14 days [137]. Recently, carbon tetrachloride cold plasma was shown to produce chlorinated CNTs [138]. Chlorine is fixed to the nanotubes' edges and flaws as a result of the operation.

A method of purification for CNT polluted by carbon impurities was used because of the low sensitivity of CNTs to bromination. However, the C-Br bond is more reactive than the comparable iodinated fluoro- or chloro-derivatives. CNTs bromination needed relatively difficult conditions as compared to other carbon nanostructures. With bromine in the liquid, gas, or plasma phases, it can only be done by electrochemical, electrothermal, or microwave processes at a higher temperature. Despite the improvement that has been shown, bromination causes a small amount of CNT degradation and fragmentation [139]. Bromine-containing SWCNT was demonstrated to have metallic properties [140]. In [141], the CNTs were combined with liquid bromine for 10 days at 55°C and then repeatedly washed with CCl4, carbon tetrachloride.The perpendicular arrangement of bromine atoms in relation to the CNT surface was readily seen using TEM. Br atom conjugation was made possible in the graphite structure of CNTs (2.8 percent weight) by electrochemical oxidation of inorganic salts such KBr [142]. Additionally, CNTs that had already been treated in aqueous solution were brominated using microwaves. A high Br atom concentration of 5-8 percent by weight was archived [143]. Elemental bromine and a group of Lewis acids (BBr3, BF3-Et2O, AlBr3, FeBr3, ZnBr2, etc.) may also be used to chemically bromine CNT, producing materials with 10–20% wt Br content. According to Bulusheva, the suction of CNT in liquid Br yields the C17Br stoichiometry. The covalent bromination process with a total weight of 4.9 % in CCl4 solution at microwave irradiation, and a cool CH3Br plasma were described in [144]. N-bromosuccinimide, NH4NO3/NBS, and Br2 were used in an electrophilic addition and radical reaction with UV light or conventional heating to archive the effective bromination [145]. In comparison to other methods, this one was proven to be the most mild, delicate, ecologically friendly, and quick. The effective bromine doping of single-walled carbon nanotube films under ultrasound was recently published [146].

The literature has covered a lot of various substitution methods, including the substitution by I, S, Si, Se, P-N, and Ar. An other technique for changing the graphitic structure of CNTs is iodination. First, a modified Hunsdiecker reaction was used to carry it out [147]. It was found that Cl, Br, and I easily produced halogenated CNTs at high temperatures and pressures. The CNTs have also been doped with iodine atoms using the straightforward solvent-thermal reaction process  and their characteristics have been examined [148]. In order to illustrate the replacement of impurities in both materials, mono- and divacancies were produced in graphene and SWCNTs using the Ar plasma treatment [149]. Using STEM and other techniques, the Ar ions were plainly visible on the surface of CNTs.

This entry is adapted from the peer-reviewed paper 10.3390/ma15155386

References

  1. Kharlamova, M.V. Electronic Properties of Pristine and Modified Single-Walled Carbon Nanotubes. Phys.-Uspekhi 2013, 56, 1047–1073. https://doi.org/10.3367/UFNE.0183.201311A.1145.
  2. Kharlamova, M.V. Advances in Tailoring the Electronic Properties of Single-Walled Carbon Nanotubes. Prog. Mater. Sci. 2016, 77, 125–211. https://doi.org/10.1016/J.PMATSCI.2015.09.001.
  3. Burdanova, M.G.; Liu, M.; Staniforth, M.; Zheng, Y.; Xiang, R.; Chiashi, S.; Anisimov, A.; Kauppinen, E.I.; Maruyama, S.; Lloyd-Hughes, J. Intertube Excitonic Coupling in Nanotube Van Der Waals Heterostructures (Adv. Funct. Mater. 11/2022). Adv. Funct. Mater. 2022, 32, 2270069. https://doi.org/10.1002/ADFM.202270069.
  4. Kashtiban, R.J.; Burdanova, M.G.; Vasylenko, A.; Wynn, J.; Medeiros, P.V.C.; Ramasse, Q.; Morris, A.J.; Quigley, D.; Lloyd-Hughes, J.; Sloan, J. Linear and Helical Cesium Iodide Atomic Chains in Ultranarrow Single-Walled Carbon Nanotubes: Impact on Optical Properties. ACS Nano 2021, 15, 13389–13398. https://doi.org/10.1021/ACSNANO.1C03705/ASSET/IMAGES/LARGE/NN1C03705_0006.JPEG.
  5. Burdanova, M.G.; Tsapenko, A.P.; Kharlamova, M.V.; Kauppinen, E.I.; Gorshunov, B.P.; Kono, J.; Lloyd-Hughes, J. A Review of the Terahertz Conductivity and Photoconductivity of Carbon Nanotubes and Heteronanotubes. Adv. Opt. Mater. 2021, 9, 2101042. https://doi.org/10.1002/ADOM.202101042.
  6. Jouni, M.; Fedorko, P.; Celle, C.; Djurado, D.; Chenevier, P.; Faure-Vincent, J. Conductivity vs Functionalization in Sin-gle-Walled Carbon Nanotube Films. SN Appl. Sci. 2022, 4, 132. https://doi.org/10.1007/S42452-022-05016-W/FIGURES/4.
  7. Kharlamova, M.V.; Kramberger, C. Applications of Filled Single-Walled Carbon Nanotubes: Progress, Challenges, and Per-spectives. Nanomaterials 2021, 11, 2863. https://doi.org/10.3390/NANO11112863.
  8. Burdanova, M.G.; Katyba, G.M.; Kashtiban, R.; Komandin, G.A.; Butler-Caddle, E.; Staniforth, M.; Mkrtchyan, A.A.; Kras-nikov, D. v.; Gladush, Y.G.; Sloan, J.; et al. Ultrafast, High Modulation Depth Terahertz Modulators Based on Carbon Nanotube Thin Films. Carbon 2021, 173, 245–252. https://doi.org/10.1016/J.CARBON.2020.11.008.
  9. Burdanova, M.G.; Tsapenko, A.P.; Satco, D.A.; Kashtiban, R.; Mosley, C.D.W.; Monti, M.; Staniforth, M.; Sloan, J.; Gladush, Y.G.; Nasibulin, A.G.; et al. Giant Negative Terahertz Photoconductivity in Controllably Doped Carbon Nanotube Networks. ACS Photonics 2019, 6, 1058–1066. https://doi.org/10.1021/ACSPHOTONICS.9B00138/SUPPL_FILE/PH9B00138_SI_001.PDF.
  10. Gladush, Y.; Mkrtchyan, A.A.; Kopylova, D.S.; Ivanenko, A.; Nyushkov, B.; Kobtsev, S.; Kokhanovskiy, A.; Khegai, A.; Melkumov, M.; Burdanova, M.; et al. Ionic Liquid Gated Carbon Nanotube Saturable Absorber for Switchable Pulse Generation. Nano Lett. 2019, 19, 5836–5843. https://doi.org/10.1021/ACS.NANOLETT.9B01012/SUPPL_FILE/NL9B01012_SI_001.AVI.
  11. Thostenson, E.T.; Ren, Z.; Chou, T.W. Advances in the Science and Technology of Carbon Nanotubes and Their Composites: A Review. Compos. Sci. Technol. 2001, 61, 1899–1912. https://doi.org/10.1016/S0266-3538(01)00094-X.
  12. Cui, J.; Burghard, M.; Kern, K. Reversible Sidewall Osmylation of Individual Carbon Nanotubes. Nano Lett. 2003, 3, 613–615. https://doi.org/10.1021/NL034135P/ASSET/IMAGES/MEDIUM/NL034135PN00001.GIF.
  13. Paloniemi, H.; Ääritalo, T.; Laiho, T.; Liuke, H.; Kocharova, N.; Haapakka, K.; Terzi, F.; Seeber, R.; Lukkari, J. Water-Soluble Full-Length Single-Wall Carbon Nanotube Polyelectrolytes: Preparation and Characterization. J. Phys. Chem. B 2005, 109, 8634–8642. https://doi.org/10.1021/JP0443097/SUPPL_FILE/JP0443097SI20041214_080128.PDF.
  14. Nakashima, N.; Tomonari, Y.; Murakami, H. Water-Soluble Single-Walled Carbon Nanotubes via Noncovalent Side-wall-Functionalization with a Pyrene-Carrying Ammonium Ion. Chem. Lett. 2002, 31, 638–639. https://doi.org/10.1246/CL.2002.638.
  15. Guldi, D.M.; Rahman, G.M.A.; Jux, N.; Balbinot, D.; Hartnagel, U.; Tagmatarchis, N.; Prato, M. Functional Single-Wall Carbon Nanotube Nanohybrids-Associating SWNTs with Water-Soluble Enzyme Model Systems. J. Am. Chem. Soc. 2005, 127, 9830–9838. https://doi.org/10.1021/JA050930O.
  16. Kitaygorodskiy, A.; Wang, W.; Xie, S.Y.; Lin, Y.; Shiral Fernando, K.A.; Wang, X.; Qu, L.; Chen, B.; Sun, Y.P. NMR Detection of Single-Walled Carbon Nanotubes in Solution. J. Am. Chem. Soc. 2005, 127, 7517–7520. https://doi.org/10.1021/JA050342A/SUPPL_FILE/JA050342ASI20050310_065407.PDF.
  17. Katz, E.; Willner, I. Biomolecule-Functionalized Carbon Nanotubes: Applications in Nanobioelectronics. Chemphyschem 2004, 5, 1084–1104. https://doi.org/10.1002/CPHC.200400193.
  18. Moore, V.C.; Strano, M.S.; Haroz, E.H.; Hauge, R.H.; Smalley, R.E.; Schmidt, J.; Talmon, Y. Individually Suspended Sin-gle-Walled Carbon Nanotubes in Various Surfactants. Nano Lett. 2003, 3, 1379–1382. https://doi.org/10.1021/NL034524J/SUPPL_FILE/NL034524JSI20030821_024512.PDF.
  19. Matarredona, O.; Rhoads, H.; Li, Z.; Harwell, J.H.; Balzano, L.; Resasco, D.E. Dispersion of Single-Walled Carbon Nanotubes in Aqueous Solutions of the Anionic Surfactant NaDDBS. J. Phys. Chem. B 2003, 107, 13357–13367. https://doi.org/10.1021/JP0365099.
  20. Islam, M.F.; Rojas, E.; Bergey, D.M.; Johnson, A.T.; Yodh, A.G. High Weight Fraction Surfactant Solubilization of Single-Wall Carbon Nanotubes in Water. Nano Lett. 2003, 3, 269–273. https://doi.org/10.1021/NL025924U/ASSET/IMAGES/MEDIUM/NL025924UN00001.GIF.
  21. Tasis, D.; Tagmatarchis, N.; Bianco, A.; Prato, M. Chemistry of Carbon Nanotubes. Chem. Rev. 2006, 106, 1105–1136. https://doi.org/10.1021/CR050569O.
  22. Monthioux, M.; Flahaut, E.; Cleuziou, J.P. Hybrid Carbon Nanotubes: Strategy, Progress, and Perspectives. J. Mater. Res. 2006, 21, 2774–2793. https://doi.org/10.1557/JMR.2006.0366.
  23. Balasubramanian, K.; Burghard, M. Chemically Functionalized Carbon Nanotubes. Small 2005, 1, 180–192. https://doi.org/10.1002/SMLL.200400118.
  24. Bahr, J.L.; Tour, J.M. Covalent Chemistry of Single-Wall Carbon Nanotubes. J. Mater. Chem. 2002, 12, 1952–1958. https://doi.org/10.1039/B201013P.
  25. Banerjee, S.; Kahn, M.G.C.; Wong, S.S. Rational Chemical Strategies for Carbon Nanotube Functionalization. Chem.–A Eur. J. 2003, 9, 1898–1908. https://doi.org/10.1002/CHEM.200204618.
  26. Banerjee, S.; Hemraj-Benny, T.; Wong, S.S. Covalent Surface Chemistry of Single-Walled Carbon Nanotubes. Adv. Mater. 2005, 17, 17–29. https://doi.org/10.1002/ADMA.200401340.
  27. Controlled Synthesis and Modification of Carbon Nanotubes and C60: Carbon Nanostructures for Advanced Polymeric Composite Materials-Dai-2001-Advanced Materials-Wiley Online Library. Available online: https://onlinelibrary.wiley.com/doi/10.1002/1521-4095%28200107%2913%3A12/13%3C899%3A%3AAID-ADMA899%3E3.0.CO%3B2-G (accessed on 24 July 2022).
  28. Davis, J.J.; Coleman, K.S.; Azamian, B.R.; Bagshaw, C.B.; Green, M.L.H. Chemical and Biochemical Sensing with Modified Single Walled Carbon Nanotubes. Chem.–A Eur. J. 2003, 9, 3732–3739. https://doi.org/10.1002/CHEM.200304872.
  29. de La Torre, G.; Blau, W.; Torres, T. A Survey on the Functionalization of Single-Walled Nanotubes. The Chemical of Phthal-ocyanine Moieties. Nanotechnology 2003, 14, 765. https://doi.org/10.1088/0957-4484/14/7/312.
  30. Dyke, C.A.; Tour, J.M. Solvent-Free Functionalization of Carbon Nanotubes. J. Am. Chem. Soc. 2003, 125, 1156–1157. https://doi.org/10.1021/JA0289806/SUPPL_FILE/JA0289806-4_S1.PDF.
  31. Dyke, C.A.; Tour, J.M. Overcoming the Insolubility of Carbon Nanotubes Through High Degrees of Sidewall Functionalization. Chem.–A Eur. J. 2004, 10, 812–817. https://doi.org/10.1002/CHEM.200305534.
  32. Fischer, J.E. Chemical Doping of Single-Wall Carbon Nanotubes. Acc. Chem. Res. 2002, 35, 1079–1086. https://doi.org/10.1021/AR0101638.
  33. Muñoz-Écija, T.; Vargas-Quesada, B.; Chinchilla-Rodríguez, Z. Identification and Visualization of the Intellectual Structure and the Main Research Lines in Nanoscience and Nanotechnology at the Worldwide Level. J. Nanoparticle Res. 2017, 19, 62. https://doi.org/10.1007/S11051-016-3732-3.
  34. Hilding, J.; Grulke, E.A.; Zhang, Z.G.; Lockwood, F. Dispersion of Carbon Nanotubes in Liquids. J. Dispers. Sci. Technol. 2007, 24, 1–41. https://doi.org/10.1081/DIS-120017941.
  35. Atzrodt, J.; Derdau, V.; Kerr, W.; Reid, M. Applications of Hydrogen Isotopes in the Life Sciences. Angew. Chem. Int. Ed. 2017, 23, 627–628. https://doi.org/10.1002/(ISSN)1521-3773.
  36. Hirsch, A.; Vostrowsky, O. Functionalization of Carbon Nanotubes. Top. Curr. Chem. 2005, 245, 193–237. https://doi.org/10.1007/B98169.
  37. Lu, X.; Chen, Z. Curved Pi-Conjugation, Aromaticity, and the Related Chemistry of Small Fullerenes (
  38. Niyogi, S.; Hamon, M.A.; Hu, H.; Zhao, B.; Bhowmik, P.; Sen, R.; Itkis, M.E.; Haddon, R.C. Chemistry of Single-Walled Carbon Nanotubes. Acc. Chem. Res. 2002, 35, 1105–1113. https://doi.org/10.1021/AR010155R.
  39. Lukzen, N.N.; Ivanov, K.L.; Morozov, V.A.; Sagdeev, R.Z.; Kattnig, D.; Grampp, G. Chemical Polarization of Electrons of Spin-Correlated Radical Ion Pairs in Nanotubes. Dokl. Phys. Chem. 2006, 409, 233–236. https://doi.org/10.1134/S0012501606080045.
  40. Sinnott, S.B. Chemical Functionalization of Carbon Nanotubes. J. Nanosci. Nanotechnol. 2002, 2, 113–123. https://doi.org/10.1166/JNN.2002.107.
  41. Sun, Y.P.; Fu, K.; Lin, Y.; Huang, W. Functionalized Carbon Nanotubes: Properties and Applications. Acc. Chem. Res. 2002, 35, 1096–1104. https://doi.org/10.1021/AR010160V.
  42. Tasis, D.; Tagmatarchis, N.; Georgakilas, V.; Prato, M. Soluble Carbon Nanotubes. Chem.–A Eur. J. 2003, 9, 4000–4008. https://doi.org/10.1002/CHEM.200304800.
  43. Terrones, M. Science and Technology of the Twenty-First Century: Synthesis, Properties, and Applications of Carbon Nano-tubes. Annu. Rev. Mater. Res. 2003, 33, 419–501. https://doi.org/10.1146/ANNUREV.MATSCI.33.012802.100255.
  44. Mickelson, E.T.; Huffman, C.B.; Rinzler, A.G.; Smalley, R.E.; Hauge, R.H.; Margrave, J.L. Fluorination of Single-Wall Carbon Nanotubes. Chem. Phys. Lett. 1998, 296, 188–194. https://doi.org/10.1016/S0009-2614(98)01026-4.
  45. PLANK, N. Functionalisation of Carbon Nanotubes for Molecular Electronics. Microelectron. Eng. 2004, 578–582. https://doi.org/10.1016/J.MEE.2004.02.088.
  46. Kelly, K.F.; Chiang, I.W.; Mickelson, E.T.; Hauge, R.H.; Margrave, J.L.; Wang, X.; Scuseria, G.E.; Radloff, C.; Halas, N.J. Insight into the Mechanism of Sidewall Functionalization of Single-Walled Nanotubes: An STM Study. Chem. Phys. Lett. 1999, 313, 445–450. https://doi.org/10.1016/S0009-2614(99)00973-2.
  47. An, K.H.; Heo, J.G.; Jeon, K.G.; Bae, D.J.; Jo, C.; Yang, C.W.; Park, C.Y.; Lee, Y.H.; Lee, Y.S.; Chung, Y.S. X-Ray Photoemission Spectroscopy Study of Fluorinated Single-Walled Carbon Nanotubes. Appl. Phys. Lett. 2002, 80, 4235. https://doi.org/10.1063/1.1482801.
  48. Lee, Y.S.; Cho, T.H.; Lee, B.K.; Rho, J.S.; An, K.H.; Lee, Y.H. Surface Properties of Fluorinated Single-Walled Carbon Nanotubes. J. Fluor. Chem. 2003, 120, 99–104. https://doi.org/10.1016/S0022-1139(02)00316-0.
  49. Plank, N.O.V.; Jiang, L.; Cheung, R. Fluorination of Carbon Nanotubes in CF4 Plasma. Appl. Phys. Lett. 2003, 83, 2426. https://doi.org/10.1063/1.1611621.
  50. Esumi, K.; Ishigami, M.; Nakajima, A.; Sawada, K.; Honda, H. Chemical Treatment of Carbon Nanotubes. Carbon N Y 1996, 34, 279–281. https://doi.org/10.1016/0008-6223(96)83349-5.
  51. Yu, R.; Chen, L.; Liu, Q.; Lin, J.; Tan, K.L.; Ng, S.C.; Chan, H.S.O.; Xu, G.Q.; Hor, T.S.A. Platinum Deposition on Carbon Nanotubes via Chemical Modification. Chem. Mater. 1998, 10, 718–722. https://doi.org/10.1021/CM970364Z.
  52. Wang, Z.; Shirley, M.D.; Meikle, S.T.; Whitby, R.L.D.; Mikhalovsky, S.V. The Surface Acidity of Acid Oxidised Multi-Walled Carbon Nanotubes and the Influence of in-Situ Generated Fulvic Acids on Their Stability in Aqueous Dispersions. Carbon N Y 2009, 47, 73–79. https://doi.org/10.1016/J.CARBON.2008.09.038.
  53. Datsyuk, V.; Kalyva, M.; Papagelis, K.; Parthenios, J.; Tasis, D.; Siokou, A.; Kallitsis, I.; Galiotis, C. Chemical Oxidation of Multiwalled Carbon Nanotubes. Carbon N Y 2008, 46, 833–840. https://doi.org/10.1016/J.CARBON.2008.02.012.
  54. Lu, C.; Chiu, H. Chemical Modification of Multiwalled Carbon Nanotubes for Sorption of Zn2+ from Aqueous Solution. Chem. Eng. J. 2008, 139, 462–468. https://doi.org/10.1016/J.CEJ.2007.08.013.
  55. Hernadi, K.; Siska, A.; Thiên-Nga, L.; Forró, L.; Kiricsi, I. Reactivity of Different Kinds of Carbon during Oxidative Purification of Catalytically Prepared Carbon Nanotubes. Solid State Ion. 2001, 141, 203–209. https://doi.org/10.1016/S0167-2738(01)00789-5.
  56. Zhang, N.; Xie, J.; Varadan, V.K. Functionalization of Carbon Nanotubes by Potassium Permanganate Assisted with Phase Transfer Catalyst. Smart Mater. Struct. 2002, 11, 962–965. https://doi.org/10.1088/0964-1726/11/6/318.
  57. Lu, C.; Liu, C.; Rao, G.P. Comparisons of Sorbent Cost for the Removal of Ni2+ from Aqueous Solution by Carbon Nanotubes and Granular Activated Carbon. J. Hazard. Mater. 2008, 151, 239–246. https://doi.org/10.1016/J.JHAZMAT.2007.05.078.
  58. Huang, J.Q.; Zhang, Q.; Zhao, M.Q.; Wei, F. The Release of Free Standing Vertically-Aligned Carbon Nanotube Arrays from a Substrate Using CO2 Oxidation. Carbon N Y 2010, 5, 1441–1450. https://doi.org/10.1016/J.CARBON.2009.12.038.
  59. Lu, M.; Lu, M.; He, Q.; Li, Y.; Xu, C.; Ji, K.; Dai, Z. Influence of Carbon Dioxide Plasma Treatment on the Dry Adhesion of Vertical Aligned Carbon Nanotube Arrays. Nanotechnology 2020, 31, 345701. https://doi.org/10.1088/1361-6528/AB903F.
  60. Ran, M.; Sun, W.; Liu, Y.; Chu, W.; Jiang, C. Functionalization of Multi-Walled Carbon Nanotubes Using Water-Assisted Chemical Vapor Deposition. J. Solid State Chem. 2013, 197, 517–522. https://doi.org/10.1016/J.JSSC.2012.08.014.
  61. Ajayan, P.M.; Ebbesen, T.W.; Ichihashi, T.; Iijima, S.; Tanigaki, K.; Hiura, H. Opening Carbon Nanotubes with Oxygen and Implications for Filling. Nature 1993, 362, 522–525. https://doi.org/10.1038/362522a0.
  62. Wang, X.; Ouyang, C.; Dou, S.; Liu, D.; Wang, S. Oxidized Carbon Nanotubes as an Efficient Metal-Free Electrocatalyst for the Oxygen Reduction Reaction. RSC Adv. 2015, 5, 41901–41904. https://doi.org/10.1039/C5RA05172J.
  63. Ye, B.; Kim, S.I.; Lee, M.; Ezazi, M.; Kim, H.D.; Kwon, G.; Lee, D.H. Synthesis of Oxygen Functionalized Carbon Nanotubes and Their Application for Selective Catalytic Reduction of NOx with NH3. RSC Adv. 2020, 10, 16700–16708. https://doi.org/10.1039/D0RA01665A.
  64. Morales-Lara, F.; Pérez-Mendoza, M.J.; Altmajer-Vaz, D.; García-Román, M.; Melguizo, M.; López-Garzón, F.J.; Domin-go-García, M. Functionalization of Multiwall Carbon Nanotubes by Ozone at Basic PH. Comparison with Oxygen Plasma and Ozone in Gas Phase. J. Phys. Chem. C 2013, 117, 11647–11655. https://doi.org/10.1021/JP4017097/SUPPL_FILE/JP4017097_SI_001.PDF.
  65. Peng, K.; Liu, L.Q.; Li, H.; Meyer, H.; Zhang, Z. Room Temperature Functionalization of Carbon Nanotubes Using an Ozone/Water Vapor Mixture. Carbon N Y 2011, 1, 70–76. https://doi.org/10.1016/J.CARBON.2010.08.043.
  66. Simmons, J.M.; Nichols, B.M.; Baker, S.E.; Marcus, M.S.; Castellini, O.M.; Lee, C.S.; Hamers, R.J.; Eriksson, M.A. Effect of Ozone Oxidation on Single-Walled Carbon Nanotubes. J. Phys. Chem. B 2006, 110, 7113–7118. https://doi.org/10.1021/JP0548422/SUPPL_FILE/JP0548422SI20060106_122507.PDF.
  67. Ng, C.M.; Manickam, S. Improved Functionalization and Recovery of Carboxylated Carbon Nanotubes Using the Acoustic Cavitation Approach. Chem. Phys. Lett. 2013, 557, 97–101. https://doi.org/10.1016/J.CPLETT.2012.11.095.
  68. Martín, O.; Gutierrez, H.R.; Maroto-Valiente, A.; Terrones, M.; Blanco, T.; Baselga, J. An Efficient Method for the Carboxylation of Few-Wall Carbon Nanotubes with Little Damage to Their Sidewalls. Mater. Chem. Phys. 2013, 140, 499–507. https://doi.org/10.1016/J.MATCHEMPHYS.2013.03.060.
  69. Grujicic, M.; Cao, G.; Rao, A.M.; Tritt, T.M.; Nayak, S. UV-Light Enhanced Oxidation of Carbon Nanotubes. Appl. Surf. Sci. 2003, 214, 289–303. https://doi.org/10.1016/S0169-4332(03)00361-1.
  70. Dutta, D.; Dubey, R.; Yadav, J.; Shami, T.C.; Rao, K.U.B.; Dutta, D.; Dubey, R.; Yadav, J.; Shami, T.C.; Rao, K.U.B. Preparation of Spongy Microspheres Consisting of Functionalized Multiwalled Carbon Nanotubes. New Carbon Mater. 2011, 26, 98–102. https://doi.org/10.1016/S1872-5805(11)60069-3.
  71. Zhou, W.; Ooi, Y.H.; Russo, R.; Papanek, P.; Luzzi, D.E.; Fischer, J.E.; Bronikowski, M.J.; Willis, P.A.; Smalley, R.E. Structural Characterization and Diameter-Dependent Oxidative Stability of Single Wall Carbon Nanotubes Synthesized by the Catalytic Decomposition of CO. Chem. Phys. Lett. 2001, 350, 6–14. https://doi.org/10.1016/S0009-2614(01)01237-4.
  72. Singh, D.K.; Iyer, P.K.; Giri, P.K. Diameter Dependence of Oxidative Stability in Multiwalled Carbon Nanotubes: Role of Defects and Effect of Vacuum Annealing. J. Appl. Phys. 2010, 108, 084313. https://doi.org/10.1063/1.3491022.
  73. Ye, J.; Wu, S.; Ni, K.; Tan, Z.; Xu, J.; Tao, Z.; Zhu, Y. Diameter-Sensitive Breakdown of Single-Walled Carbon Nanotubes upon KOH Activation. ChemPhysChem 2017, 18, 1929–1936. https://doi.org/10.1002/CPHC.201700300.
  74. Avilés, F.; Sierra-Chi, C.A.; Nistal, A.; May-Pat, A.; Rubio, F.; Rubio, J. Influence of Silane Concentration on the Silanization of Multiwall Carbon Nanotubes. Carbon N Y 2013, 57, 520–529. https://doi.org/10.1016/J.CARBON.2013.02.031.
  75. Ma, P.C.; Kim, J.K.; Tang, B.Z. Functionalization of Carbon Nanotubes Using a Silane Coupling Agent. Carbon N Y 2006, 44, 3232–3238. https://doi.org/10.1016/J.CARBON.2006.06.032.
  76. Yaghoubi, A.; Alavi Nikje, M.M. Silanization of Multi-Walled Carbon Nanotubes and the Study of Its Effects on the Properties of Polyurethane Rigid Foam Nanocomposites. Compos. Part A Appl. Sci. Manuf. 2018, 109, 338–344. https://doi.org/10.1016/J.COMPOSITESA.2018.03.028.
  77. Hamon, M.A.; Hui, H.; Bhowmik, P.; Itkis, H.M.E.; Haddon, R.C. Ester-Functionalized Soluble Single-Walled Carbon Nano-tubes. Appl. Phys. A 2002, 74, 333–338. https://doi.org/10.1007/S003390201281.
  78. Malikov, E.Y.; Muradov, M.B.; Akperov, O.H.; Eyvazova, G.M.; Puskás, R.; Madarász, D.; Nagy, L.; Kukovecz, Á.; Kónya, Z. Synthesis and Characterization of Polyvinyl Alcohol Based Multiwalled Carbon Nanotube Nanocomposites. Phys. E Low-Dimens. Syst. Nanostructures 2014, 61, 129–134. https://doi.org/10.1016/J.PHYSE.2014.03.026.
  79. Basiuk, E.V.; Basiuk, V.A.; Bañuelos, J.G.; Saniger-Blesa, J.M.; Pokrovskiy, V.A.; Gromovoy, T.Y.; Mischanchuk, A. v.; Mis-chanchuk, B.G. Interaction of Oxidized Single-Walled Carbon Nanotubes with Vaporous Aliphatic Amines. J. Phys. Chem. B 2002, 106, 1588–1597. https://doi.org/10.1021/JP0120110.
  80. Lavorgna, M.; Romeo, V.; Martone, A.; Zarrelli, M.; Giordano, M.; Buonocore, G.G.; Qu, M.Z.; Fei, G.X.; Xia, H.S. Silanization and Silica Enrichment of Multiwalled Carbon Nanotubes: Synergistic Effects on the Thermal-Mechanical Properties of Epoxy Nanocomposites. Eur. Polym. J. 2013, 49, 428–438. https://doi.org/10.1016/J.EURPOLYMJ.2012.10.003.
  81. Gammoudi, H.; Belkhiria, F.; Helali, S.; Assaker, I. ben; Gammoudi, I.; Morote, F.; Souissi, A.; Karyaoui, M.; Amlouk, M.; Co-hen-Bouhacina, T.; et al. Chemically Grafted of Single-Walled Carbon Nanotubes onto a Functionalized Silicon Surface. J. Alloy Compd. 2017, 694, 1036–1044. https://doi.org/10.1016/J.JALLCOM.2016.10.123.
  82. Chua, T.P.; Mariatti, M.; Azizan, A.; Rashid, A.A. Effects of Surface-Functionalized Multi-Walled Carbon Nanotubes on the Properties of Poly(Dimethyl Siloxane) Nanocomposites. Compos. Sci. Technol. 2010, 70, 671–677. https://doi.org/10.1016/J.COMPSCITECH.2009.12.023.
  83. Zhou, H.; Zhang, C.; Li, H.; Du, Z. Fabrication of Silica Nanoparticles on the Surface of Functionalized Multi-Walled Carbon Nanotubes. Carbon N Y 2011, 1, 126–132. https://doi.org/10.1016/J.CARBON.2010.08.051.
  84. Valentini, L.; Macan, J.; Armentano, I.; Mengoni, F.; Kenny, J.M. Modification of Fluorinated Single-Walled Carbon Nanotubes with Aminosilane Molecules. Carbon N Y 2006, 44, 2196–2201. https://doi.org/10.1016/J.CARBON.2006.03.007.
  85. Lin, T.W.; Salzmann, C.G.; Shao, L.D.; Yu, C.H.; Green, M.L.H.; Tsang, S.C. Polyethylene Glycol Grafting and Attachment of Encapsulated Magnetic Iron Oxide Silica Nanoparticles onto Chlorosilanized Single-Wall Carbon Nanotubes. Carbon N Y 2009, 6, 1415–1420. https://doi.org/10.1016/J.CARBON.2008.11.034.
  86. Cui, J.B.; Daghlian, C.P.; Gibson, U.J. Solubility and Electrical Transport Properties of Thiolated Single-Walled Carbon Nano-tubes. J. Appl. Phys. 2005, 98, 044320. https://doi.org/10.1063/1.2035893.
  87. Lee, Y.S. Syntheses and Properties of Fluorinated Carbon Materials. J. Fluor. Chem. 2007, 128, 392–403. https://doi.org/10.1016/J.JFLUCHEM.2006.11.014.
  88. Adamska, M.; Narkiewicz, U. Fluorination of Carbon Nanotubes−A Review. J. Fluor. Chem. 2017, 200, 179–189. https://doi.org/10.1016/J.JFLUCHEM.2017.06.018.
  89. Pulikkathara, M.X.; Khabashesku, V.N. Covalent Sidewall Functionalization of Single-Walled Carbon Nanotubes by Amino Acids. Russ. Chem. Bull. 2009, 57, 1054–1062. https://doi.org/10.1007/S11172-008-0134-4.
  90. Kónya, Z.; Vesselenyi, I.; Niesz, K.; Kukovecz, A.; Demortier, A.; Fonseca, A.; Delhalle, J.; Mekhalif, Z.; Nagy, J.B.; Koós, A.A.; et al. Large Scale Production of Short Functionalized Carbon Nanotubes. Chem. Phys. Lett. 2002, 360, 429–435. https://doi.org/10.1016/S0009-2614(02)00900-4.
  91. Lee, W.H.; Kim, S.J.; Lee, W.J.; Lee, J.G.; Haddon, R.C.; Reucroft, P.J. X-Ray Photoelectron Spectroscopic Studies of Surface Modified Single-Walled Carbon Nanotube Material. Appl. Surf. Sci. 2001, 181, 121–127. https://doi.org/10.1016/S0169-4332(01)00381-6.
  92. Duesberg, G.S.; Graupner, R.; Downes, P.; Minett, A.; Ley, L.; Roth, S.; Nicoloso, N. Hydrothermal Functionalisation of Sin-gle-Walled Carbon Nanotubes. Synth. Met. 2004, 142, 263–266. https://doi.org/10.1016/J.SYNTHMET.2003.09.009.
  93. Barthos, R.; Méhn, D.; Demortier, A.; Pierard, N.; Morciaux, Y.; Demortier, G.; Fonseca, A.; Nagy, J.B. Functionalization of Single-Walled Carbon Nanotubes by Using Alkyl-Halides. Carbon N Y 2005, 43, 321–325. https://doi.org/10.1016/J.CARBON.2004.09.018.
  94. Mazov, I.; Krasnikov, D.; Stadnichenko, A.; Kuznetsov, V.; Romanenko, A.; Anikeeva, O.; Tkachev, E. Direct Vapor-Phase Bromination of Multiwall Carbon Nanotubes. J. Nanotechnol. 2012, 2012, 954084. https://doi.org/10.1155/2012/954084.
  95. Bulusheva, L.G.; Okotrub, A.V.; Flahaut, E.; Asanov, I.P.; Gevko, P.N.; Koroteev, V.O.; Fedoseeva, Y.V.; Yaya, A.; Ewels, C.P. Bromination of Double-Walled Carbon Nanotubes. Chem. Mater. 2012, 24, 2708–2715. https://doi.org/10.1021/CM3006309.
  96. Tang, X.; Zhao, Y.; Jiao, Q.; Cao, Y. Hydrogenation of Multi‐walled Carbon Nanotubes in Ethylenediamine. Fuller. Nanotub. Carbon Nanostructures 2010, 18, 14–23. https://doi.org/10.1080/15363830903291697.
  97. Krueger, A. New Carbon Materials: Biological Applications of Functionalized Nanodiamond Materials. Chem.–A Eur. J. 2008, 14, 1382–1390. https://doi.org/10.1002/CHEM.200700987.
  98. Marshall, M.W.; Popa-Nita, S.; Shapter, J.G. Measurement of Functionalised Carbon Nanotube Carboxylic Acid Groups Using a Simple Chemical Process. Carbon N Y 2006, 44, 1137–1141. https://doi.org/10.1016/J.CARBON.2005.11.010.
  99. Nikitin, A.; Li, X.; Zhang, Z.; Ogasawara, H.; Dai, H.; Nilsson, A. Hydrogen Storage in Carbon Nanotubes through the For-mation of Stable C−H Bonds. Nano Lett. 2007, 8, 162–167. https://doi.org/10.1021/NL072325K.
  100. Froudakis, G.E. Hydrogen Storage in Nanotubes & Nanostructures. Mater. Today 2011, 14, 324–328. https://doi.org/10.1016/S1369-7021(11)70162-6.
  101. Dillon, A.C.; Jones, K.M.; Bekkedahl, T.A.; Kiang, C.H.; Bethune, D.S.; Heben, M.J. Storage of Hydrogen in Single-Walled Carbon Nanotubes. Nature 1997, 386, 377–379. https://doi.org/10.1038/386377a0.
  102. Pantarotto, D.; Singh, R.; McCarthy, D.; Erhardt, M.; Briand, J.-P.; Prato, M.; Kostarelos, K.; Bianco, A.; Pantarotto, D.-C.D.; Prato, M.; et al. Functionalized Carbon Nanotubes for Plasmid DNA Gene Delivery. Angew. Chem. Int. Ed. 2004, 43, 5242–5246. https://doi.org/10.1002/ANIE.200460437.
  103. Geng, J.; Kim, K.; Zhang, J.; Escalada, A.; Tunuguntla, R.; Comolli, L.R.; Allen, F.I.; Shnyrova, A.V.; Cho, K.R.; Munoz, D.; et al. Stochastic Transport through Carbon Nanotubes in Lipid Bilayers and Live Cell Membranes. Nature 2014, 514, 612–615. https://doi.org/10.1038/NATURE13817.
  104. Chen, L.; Xie, H.; Yu, W. Functionalization Methods of Carbon Nanotubes and Its Applications. Carbon Nanotub. Appl. Electron Devices 2011. 41, 215–222. https://doi.org/10.5772/18547.
  105. Chen, X.; Kis, A.; Zettl, A.; Bertozzi, C.R. A Cell Nanoinjector Based on Carbon Nanotubes. Proc. Natl. Acad. Sci. USA 2007, 104, 8218–8222. https://doi.org/10.1073/PNAS.0700567104.
  106. Mintmire, J.W.; Dunlap, B.I.; White, C.T.; Nielsen, P.E.; Engholm, M.; Berg, R.H.; Buchardt, O.; S.; Verschueren, A.R.M.; Dekker, C.; Derycke, V.; et al. Carbon Nanotubes with DNA Recognition. Nature 2002, 420, 761–761. https://doi.org/10.1038/420761a.
  107. Awasthi, K.; Singh, D.P.; Singh, S. Attachment of Biomolecules (Protein and DNA) to Amino-Functionalized Carbon Nano-tubes. New Carbon Mater. 2009, 24, 301–306. https://doi.org/10.1016/S1872-5805(08)60053-0.
  108. Zare, H.; Ahmadi, S.; Ghasemi, A.; Ghanbari, M.; Rabiee, N.; Bagherzadeh, M.; Karimi, M.; Webster, T.J.; Hamblin, M.R.; Mostafavi, E. Carbon Nanotubes: Smart Drug/Gene Delivery Carriers. Int. J. Nanomed. 2021, 16, 1681–1706. https://doi.org/10.2147/IJN.S299448.
  109. Villa, C.H.; Dao, T.; Ahearn, I.; Fehrenbacher, N.; Casey, E.; Rey, D.A.; Korontsvit, T.; Zakhaleva, V.; Batt, C.A.; Philips, M.R.; et al. Single-Walled Carbon Nanotubes Deliver Peptide Antigen into Dendritic Cells and Enhance IgG Responses to Tu-mor-Associated Antigens. ACS Nano 2011, 5, 5300. https://doi.org/10.1021/NN200182X.
  110. Lu, Q.; Moore, J.M.; Huang, G.; Mount, A.S.; Rao, A.M.; Larcom, L.L.; Ke, P.C. RNA Polymer Translocation with Single-Walled Carbon Nanotubes. Nano Lett. 2004, 4, 2473–2477. https://doi.org/10.1021/NL048326J.
  111. Duan, H.G.; Jha, A.; Li, X.; Tiwari, V.; Ye, H.; Nayak, P.K.; Zhu, X.L.; Li, Z.; Martinez, T.J.; Thorwart, M.; et al. Intermolecular Vibrations Mediate Ultrafast Singlet Fission. Sci. Adv. 2020, 6, 52–70. https://doi.org/10.1126/SCIADV.ABB0052/SUPPL_FILE/ABB0052_SM.PDF.
  112. Piao, Y.; Meany, B.; Powell, L.R.; Valley, N.; Kwon, H.; Schatz, G.C.; Wang, Y. Brightening of Carbon Nanotube Photolumi-nescence through the Incorporation of Sp3 Defects. Nat. Chem. 2013, 5, 840–845. https://doi.org/10.1038/nchem.1711.
  113. White, B.; Banerjee, S.; O’Brien, S.; Turro, N.J.; Herman, I.P. Zeta-Potential Measurements of Surfactant-Wrapped Individual Single-Walled Carbon Nanotubes. J. Phys. Chem. C 2007, 111, 13684–13690. https://doi.org/10.1021/JP070853E/SUPPL_FILE/JP070853ESI20070131_034755.PDF.
  114. McDonald, T.J.; Engtrakul, C.; Jones, M.; Rumbles, G.; Heben, M.J. Kinetics of PL Quenching during Single-Walled Carbon Nanotube Rebundling and Diameter-Dependent Surfactant Interactions†. J. Phys. Chem. B 2006, 110, 25339–25346. https://doi.org/10.1021/JP065281X.
  115. Britz, D.A.; Khlobystov, A.N. Noncovalent Interactions of Molecules with Single Walled Carbon Nanotubes. Chem. Soc. Rev. 2006, 35, 637–659. https://doi.org/10.1039/B507451G.
  116. Priya, B.R.; Byrne, H.J. Investigation of Sodium Dodecyl Benzene Sulfonate Assisted Dispersion and Debundling of Single-Wall Carbon Nanotubes. J. Phys. Chem. C 2007, 112, 332–337. https://doi.org/10.1021/JP0743830.
  117. Zhang, Q.; Huang, J.Q.; Qian, W.Z.; Zhang, Y.Y.; Wei, F. The Road for Nanomaterials Industry: A Review of Carbon Nanotube Production, Post-Treatment, and Bulk Applications for Composites and Energy Storage. Small 2013, 9, 1237–1265. https://doi.org/10.1002/SMLL.201203252.
  118. Wenseleers, W.; Vlasov, I.L.; Goovaerts, E.; Obraztsova, E.D.; Lobach, A.S.; Bouwen, A. Efficient Isolation and Solubilization of Pristine Single-Walled Nanotubes in Bile Salt Micelles. Adv. Funct. Mater. 2004, 14, 1105–1112. https://doi.org/10.1002/ADFM.200400130.
  119. O’Connell, M.J.; Bachilo, S.H.; Huffman, C.B.; Moore, V.C.; Strano, M.S.; Haroz, E.H.; Rialon, K.L.; Boul, P.J.; Noon, W.H.; Kittrell, C.; et al. Band Gap Fluorescence from Individual Single-Walled Carbon Nanotubes. Science 2002, 297, 593–596. https://doi.org/10.1126/SCIENCE.1072631.
  120. Zhang, C.; Wang, P.; Barnes, B.; Fortner, J.; Wang, Y. Cleanly Removable Surfactant for Carbon Nanotubes. Chem. Mater. 2021, 33, 4551–4557. https://doi.org/10.1021/ACS.CHEMMATER.1C00970/SUPPL_FILE/CM1C00970_SI_001.PDF.
  121. Rastogi, R.; Kaushal, R.; Tripathi, S.K.; Sharma, A.L.; Kaur, I.; Bharadwaj, L.M. Comparative Study of Carbon Nanotube Dispersion Using Surfactants. J. Colloid Interface Sci. 2008, 328, 421–428. https://doi.org/10.1016/J.JCIS.2008.09.015.
  122. Bai, Y.; Park, I.S.; Lee, S.J.; Bae, T.S.; Watari, F.; Uo, M.; Lee, M.H. Aqueous Dispersion of Surfactant-Modified Multiwalled Carbon Nanotubes and Their Application as an Antibacterial Agent. Carbon N Y 2011, 49, 3663–3671. https://doi.org/10.1016/J.CARBON.2011.05.002.
  123. Yun, D.J.; Kim, J.M.; Ra, H.; Byun, S.; Kim, H.; Park, G.S.; Park, S.; Rhee, S.W. The Physical/Chemical Properties and Electrode Performance Variations of SWNT Films in Consequence of Solution Based Surfactant Elimination Processes. Org. Electron. 2013, 14, 2962–2972. https://doi.org/10.1016/J.ORGEL.2013.08.021.
  124. Rossi, J.E.; Soule, K.J.; Cleveland, E.; Schmucker, S.W.; Cress, C.D.; Cox, N.D.; Merrill, A.; Landi, B.J. Removal of Sodium Dodecyl Sulfate Surfactant from Aqueous Dispersions of Single-Wall Carbon Nanotubes. J. Colloid Interface Sci. 2017, 495, 140–148. https://doi.org/10.1016/J.JCIS.2017.01.117.
  125. Urper, O.; Çakmak, İ.; Karatepe, N. Fabrication of Carbon Nanotube Transparent Conductive Films by Vacuum Filtration Method. Mater. Lett. 2018, 223, 210–214. https://doi.org/10.1016/J.MATLET.2018.03.184.
  126. Billing, B.K.; Mayank; Agnihotri, P.K.; Singh, N. Development of Pyrene-Stacked Carbon Nanotube-Based Hybrid: Meas-urement of NO3- Ions Using Fluorescence Spectroscopy. Analyst 2018, 143, 3343–3352. https://doi.org/10.1039/C8AN00286J.
  127. Liu, Z.; Galli, F.; Janssen, K.G.H.; Jiang, L.; van der Linden, H.J.; de Geus, D.C.; Voskamp, P.; Kuil, M.E.; Olsthoorn, R.C.L.; Oosterkamp, T.H.; et al. Stable Single-Walled Carbon Nanotube-Streptavidin Complex for Biorecognition. J. Phys. Chem. C 2010, 114, 4345–4352. https://doi.org/10.1021/JP911441D/SUPPL_FILE/JP911441D_SI_001.PDF.
  128. Meredith, M.T.; Minson, M.; Hickey, D.; Artyushkova, K.; Glatzhofer, D.T.; Minteer, S.D. Anthracene-Modified Multi-Walled Carbon Nanotubes as Direct Electron Transfer Scaffolds for Enzymatic Oxygen Reduction. ACS Catal. 2011, 1, 1683–1690. https://doi.org/10.1021/CS200475Q/SUPPL_FILE/CS200475Q_SI_001.PDF.
  129. Yang, X.; Lu, Y.; Ma, Y.; Li, Y.; Du, F.; Chen, Y. Noncovalent Nanohybrid of Ferrocene with Single-Walled Carbon Nanotubes and Its Enhanced Electrochemical Property. Chem. Phys. Lett. 2006, 420, 416–420. https://doi.org/10.1016/J.CPLETT.2005.11.058.
  130. Huang, X.J.; Im, H.S.; Lee, D.H.; Kim, H.S.; Choi, Y.K. Ferrocene Functionalized Single-Walled Carbon Nanotube Bundles. Hybrid Interdigitated Construction Film for l-Glutamate Detection. J. Phys. Chem. C 2006, 111, 1200–1206. https://doi.org/10.1021/JP065747B.
  131. Khripin, C.Y.; Fagan, J.A.; Zheng, M. Spontaneous Partition of Carbon Nanotubes in Polymer-Modified Aqueous Phases. J. Am. Chem. Soc. 2013, 135, 6822–6825. https://doi.org/10.1021/JA402762E/SUPPL_FILE/JA402762E_SI_001.PDF.
  132. Subbaiyan, N.K.; Cambré, S.; Parra-Vasquez, A.N.G.; Hároz, E.H.; Doorn, S.K.; Duque, J.G. Role of Surfactants and Salt in Aqueous Two-Phase Separation of Carbon Nanotubes toward Simple Chirality Isolation. ACS Nano 2014, 8, 1619–1628. https://doi.org/10.1021/NN405934Y/SUPPL_FILE/NN405934Y_SI_001.PDF.
  133. Defillet, J.; Avramenko, M.; Martinati, M.; López Carrillo, M.Á.; van der Elst, D.; Wenseleers, W.; Cambré, S. The Role of the Bile Salt Surfactant Sodium Deoxycholate in Aqueous Two-Phase Separation of Single-Wall Carbon Nanotubes Revealed by Sys-tematic Parameter Variations. Carbon N Y 2022, 195, 349–363. https://doi.org/10.1016/J.CARBON.2022.03.071.
  134. Namasivayam, M.; Andersson, M.R.; Shapter, J.G.; Koloor, R.; Ayatollahi, R.; Petrů, M.; Petrů, P. A Comparative Study on the Role of Polyvinylpyrrolidone Molecular Weight on the Functionalization of Various Carbon Nanotubes and Their Composites. Polymers 2021, 13, 2447. https://doi.org/10.3390/POLYM13152447.
  135. Monteiro-Riviere, N.A.; Inman, A.O.; Wang, Y.Y.; Nemanich, R.J. Surfactant Effects on Carbon Nanotube Interactions with Human Keratinocytes. Nanomedicine 2005, 1, 293–299. https://doi.org/10.1016/J.NANO.2005.10.007.
  136. Wang, X.; Xia, T.; Ntim, S.A.; Ji, Z.; George, S.; Meng, H.; Zhang, H.; Castranova, V.; Mitra, S.; Nel, A.E. Quantitative Tech-niques for Assessing and Controlling the Dispersion and Biological Effects of Multiwalled Carbon Nanotubes in Mammalian Tissue Culture Cells. ACS Nano 2010, 4, 7241–7252. https://doi.org/10.1021/NN102112B/SUPPL_FILE/NN102112B_SI_001.PDF.
  137. Vaisman, L.; Marom, G.; Wagner, H.D. Dispersions of Surface-Modified Carbon Nanotubes in Water-Soluble and Wa-ter-Insoluble Polymers. Adv. Funct. Mater. 2006, 16, 357–363. https://doi.org/10.1002/ADFM.200500142.
  138. Manasrah, A.D.; Laoui, T.; Zaidi, S.J.; Atieh, M.A. Effect of PEG Functionalized Carbon Nanotubes on the Enhancement of Thermal and Physical Properties of Nanofluids. Exp. Therm. Fluid Sci. 2017, 84, 231–241. https://doi.org/10.1016/J.EXPTHERMFLUSCI.2017.02.018.
  139. Sharmeen, S.; Rahman, A.F.M.M.; Lubna, M.M.; Salem, K.S.; Islam, R.; Khan, M.A. Polyethylene Glycol Functionalized Carbon Nanotubes/Gelatin-Chitosan Nanocomposite: An Approach for Significant Drug Release. Bioact. Mater. 2018, 3, 236–244. https://doi.org/10.1016/J.BIOACTMAT.2018.03.001.
  140. Taghavi, S.; Nia, A.H.; Abnous, K.; Ramezani, M. Polyethylenimine-Functionalized Carbon Nanotubes Tagged with AS1411 Aptamer for Combination Gene and Drug Delivery into Human Gastric Cancer Cells. Int. J. Pharm. 2017, 516, 301–312. https://doi.org/10.1016/J.IJPHARM.2016.11.027.
  141. Cavuslar, O.; Unal, H. Self-Assembly of DNA Wrapped Carbon Nanotubes and Asymmetrical Cyanine Dyes into Fluorescent Nanohybrids. RSC Adv. 2015, 5, 22380–22389. https://doi.org/10.1039/C5RA00236B.
  142. Kim, J.M.; Kim, S.H.; Kim, N.Y.; Ryou, M.H.; Bae, H.; Kim, J.H.; Lee, Y.G.; Lee, S.Y. Nanofibrous Conductive Binders Based on DNA-Wrapped Carbon Nanotubes for Lithium Battery Electrodes. iScience 2020, 23, 101739. https://doi.org/10.1016/J.ISCI.2020.101739.
  143. McMorrow, J.; Freeley, M.; Palma, M. DNA-Wrapped Single-Walled Carbon Nanotube Assemblies. Ind. Eng. Chem. Res. 2017, 56, 5302–5308. https://doi.org/10.1021/ACS.IECR.7B00429/SUPPL_FILE/IE7B00429_SI_001.PDF.
  144. Streit, J.K.; Fagan, J.A.; Zheng, M. A Low Energy Route to DNA-Wrapped Carbon Nanotubes via Replacement of Bile Salt Surfactants. Anal. Chem. 2017, 89, 10496–10503. https://doi.org/10.1021/ACS.ANALCHEM.7B02637/SUPPL_FILE/AC7B02637_SI_001.PDF.
  145. Singh, R.; Pantarotto, D.; McCarthy, D.; Chaloin, O.; Hoebeke, J.; Partidos, C.D.; Briand, J.P.; Prato, M.; Bianco, A.; Kostarelos, K. Binding and Condensation of Plasmid DNA onto Functionalized Carbon Nanotubes: Toward the Construction of Nano-tube-Based Gene Delivery Vectors. J. Am. Chem. Soc. 2005, 127, 4388–4396. https://doi.org/10.1021/JA0441561/SUPPL_FILE/JA0441561SI20041210_125054.PDF.
  146. Vardharajula, S.; Ali, S.Z.; Tiwari, P.M.; Eroǧlu, E.; Vig, K.; Dennis, V.A.; Singh, S.R. Functionalized Carbon Nanotubes: Bi-omedical Applications. Int. J. Nanomed. 2012, 7, 5361–5374. https://doi.org/10.2147/IJN.S35832.
  147. Shkodra, B.; Petrelli, M.; Costa Angeli, M.A.; Garoli, D.; Nakatsuka, N.; Lugli, P.; Petti, L. Electrolyte-Gated Carbon Nanotube Field-Effect Transistor-Based Biosensors: Principles and Applications. Appl. Phys. Rev. 2021, 8, 041325. https://doi.org/10.1063/5.0058591.
  148. Burdanova, M.G.; Kharlamova, M.V.; Kramberger, C.; Nikitin, M.P. Applications of Pristine and Functionalized Carbon Nanotubes, Graphene, and Graphene Nanoribbons in Biomedicine. Nanomaterials 2021, 11, 3020. https://doi.org/10.3390/NANO11113020.
  149. Wu, B.; Ou, Z.; Xing, D. Functional Single-Walled Carbon Nanotubes/Chitosan Conjugate for Tumor Cells Targeting. In Eighth International Conference on Photonics and Imaging in Biology and Medicine (PIBM 2009); SPIE: Bellingham, WA, USA, 2009; Volume 7519, pp.142–149.
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