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Dumur, F. Bis-Chalcone-Based Photoinitiators of Polymerization. Encyclopedia. Available online: https://encyclopedia.pub/entry/10917 (accessed on 29 March 2024).
Dumur F. Bis-Chalcone-Based Photoinitiators of Polymerization. Encyclopedia. Available at: https://encyclopedia.pub/entry/10917. Accessed March 29, 2024.
Dumur, Fréderic. "Bis-Chalcone-Based Photoinitiators of Polymerization" Encyclopedia, https://encyclopedia.pub/entry/10917 (accessed March 29, 2024).
Dumur, F. (2021, June 16). Bis-Chalcone-Based Photoinitiators of Polymerization. In Encyclopedia. https://encyclopedia.pub/entry/10917
Dumur, Fréderic. "Bis-Chalcone-Based Photoinitiators of Polymerization." Encyclopedia. Web. 16 June, 2021.
Bis-Chalcone-Based Photoinitiators of Polymerization
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Over the past several decades, photopolymerization has become an active research field, and the ongoing efforts to develop new photoinitiating systems are supported by the different applications in which this polymerization technique is involved—including dentistry, 3D and 4D printing, adhesives, and laser writing.

chalcone ketone photopolymerization photosensitizers Claisen-Schmidt condensation

1. Introduction

Polymerization consists of converting a liquid resin into a solid, and different approaches can be used to obtain this result. As the most popular approach, the polymerization can be instigated by heat, and for this purpose, various thermal polymerization techniques have been developed over the years—such as ring-opening polymerization (ROP) [1][2], reversible addition–fragmentation chain-transfer (RAFT) polymerization [3], and nitroxide-mediated polymerization (NMP) [4][5][6]. Parallel to this, light can also be used to generate initiating species. While, historically, photopolymerization was mostly based on UV photoinitiating systems, UV light is now the focus of numerous safety concerns, such that a great deal of effort is now being devoted to developing visible light photoinitiating systems offering safer working conditions for the operator (no skin or eye damage) [7][8][9][10][11][12][13][14][15][16]. Furthermore, improved light penetration can be achieved in the visible range compared to that obtained with UV light, as shown in Figure 1. Indeed, if light penetration remains limited in the UV range (600 µm), a major improvement can be achieved with visible light, which can range between 4 mm and 5 cm, depending on the irradiation wavelength [17]. As a result of this, the scope of application of photopolymerization has been totally revolutionized, since the use of near-infrared light now allows for the polymerization of thick and filled samples, which is not achievable with UV photoinitiating systems [18][19][20]. The development of visible light photoinitiating systems is also supported by the easy access to cheap, compact, lightweight, and energy-saving irradiation sources such as light-emitting diodes (LEDs) [21][22]. Faced with this easy availability of LEDs with tunable irradiation wavelengths, the demand for photopolymerizable resins activable at these different wavelengths has similarly increased. In particular, numerous photoinitiating systems activable at 405 nm have been developed over the last several years—this wavelength being the wavelength currently in use for 3D printers [23][24][25][26][27][28]. Interest in photopolymerization is also supported by the different advantages this polymerization technique offers compared to traditional thermal polymerization, which can only be realized in solution. Thus, photopolymerization can be carried out in solvent-free conditions so that the release of volatile organic compounds (VOCs) can be advantageously avoided [29][30][31][32]. Natural compounds, photoinitiators, and monomers issued from renewable resources can also be used to elaborate photoinitiating systems and polymers, addressing the environmental impact and the toxicity issues raised by photopolymerization, and by polymerization more generally [33]. A spatial and a temporal control can also be obtained, meaning that the polymerization occurs only during the time the light is switched on, and only in the irradiated area (see Figure 2) [34][35]. The polymerization process can also be extremely fast, since it can be ended within a few seconds. This specificity is notably used advantageously with photopolymerizable glues and dental adhesives.
Figure 1. Light penetration in polystyrene latex with an average diameter of 112 nm. Reprinted with permission from Bonardi et al. [17]. Copyright 2018 American Chemical Society.
Figure 2. The different advantages of photopolymerization compared to traditional thermal polymerization.
Considering that visible light photopolymerization can be activated between 400 and 800 nm, numerous dyes absorbing in the visible range have been proposed, as exemplified with acridine-1,8-diones [36][37][38], carbazoles [39][40][41][42][43][44], pyrenes [45][46][47][48][49][50], iridium complexes, [51][52][53][54][55][56][57][58][59], copper complexes [60][61][62][63][64][65][66][67][68][69][70], squaraines [71][72][73], camphorquinones [74][75], perylenes [76][77][78], iodonium salts [79][80][81], benzophenones [82][83][84][85][86][87], cyanines [88][89], diketopyrrolopyrroles [90][91][92], helicenes [93][94], naphthalimides [95][96][97][98][99][100][101][102][103][104][105][106][107], chalcones [108][109][110][111][112][113][114], iron complexes [115][116][117][118][119][120], chromones [121][122][123], thioxanthones [124][125][126][127], dihydroanthraquinones [128], porphyrins [129][130], zinc complexes [131], acridones [132][133], push–pull dyes [134][135][136][137][138][139][140][141][142][143][144][145], phenothiazines [146], coumarins [147][148][149][150][151][152][153], flavones [154], 2,3-diphenylquinoxaline derivatives [155], and cyclohexanones [156][157][158][159]. With the aim of generating initiating species, two distinct families of photoinitiators can be distinguished: The first family, type I photoinitiators, consists of molecules that can be photochemically cleaved upon excitation. The advantage of this strategy is that only a single component is necessary to generate the initiating radicals, so the migratability of potential side products within the polymer is considerably reduced. As shown in Figure 3 with 2,2-dimethoxy-1,2-diphenylethan-1-one, upon photoexcitation, a methoxybenzyl and a benzoyl radical are simultaneously formed, improving the efficiency of the initiating step. Additionally, the two radicals can be connected to the polymer chain under growth so that no migratable residue remains within the polymer network, addressing the potential toxicity issue of the photoinitiating systems. However, while this approach is appealing, the availability of visible Type I photoinitiators remains limited, and most of the benchmark Type I photoinitiators are UV photoinitiators [160][161][162]. As a drawback, Type I photoinitiators are irreversibly consumed during the polymerization process, and so the concentration of radicals irreversibly decreases over time. Conversely, Type II photoinitiators are typically dyes absorbing in the visible range, which act as photosensitizers for UV photoinitiators. Upon photoinduced electron transfer from the excited photosensitizer towards the UV photoinitiator, initiating radicals can be generated [163]. As the most widely used UV photoinitiators, onium salts, and notably iodonium salts, which are easily accessible from various commercial sources can be cited as relevant examples [164][165][166][167]. Considering that dyes act as photosensitizers for UV photoinitiators, two-component or three-component photoinitiating systems are typically developed with Type II photoinitiators.
Figure 3. The two families of photoinitiators that have been developed in order to efficiently generate initiating radicals.
As shown in Figure 3, upon excitation of the photoinitiator with a light of an appropriate wavelength, a photoinduced electron transfer in the excited state can occur with the iodonium salt, generating phenyl radicals Ph. These radicals can typically initiate the free-radical polymerization of acrylates. However, in these conditions, the consumption of the photosensitizer is irreversible, affecting the efficiency of the system. This drawback can be addressed by the addition of a third component—generally, a sacrificial amine that will be in charge of reducing the oxidized photosensitizer, and which can be introduced to the photocurable resin. If N-vinylcarbazole (NVK) is used, this carbazole can react with the phenyl radical Ph, generating Ph–NVK, which is a radical more reactive than the initial Ph [168]. By reacting with the oxidized photosensitizer and regenerating the photosensitizer at its initial redox state, Ph–NVK can be converted into a Ph–NVK+ cation, capable of initiating the cationic polymerization of epoxides by means of free-radical-promoted cationic polymerization (FRPCP). Therefore, using these three-component systems, the concomitant polymerization of acrylates and epoxides can be simultaneously obtained, enabling access to interpenetrated polymer networks (IPN) [169][170][171][172]. The photoinitiating systems are also catalytic if three-component systems are used, the regeneration of photoinitiators enabling the system to drastically reduce its content [173][174][175]. Considering that the photosensitizer is the key element of these two- and three-component photoinitiating systems, numerous structures have been examined. In this field, chalcones are dyes that can be naturally found in numerous vegetables and flowers [176][177][178]. Chalcones can also be easily obtained via a Claisen-Schmidt condensation. Considering their ease of synthesis, their strong absorption in the visible range, and their well-established biological activities, chalcones were investigated for applications ranging from medicine [179] to solar cell applications [180][181], organic light-emitting diodes [182], and organogels [183]. Among chalcones, bis-chalcones—which can be obtained via a Claisen-Schmidt condensation of aldehydes with cyclic aliphatic ketones in basic conditions—have been less studied in the literature than mono-chalcones [109][184]. Moreover, these structures remain of interest, especially for photopolymerization. Indeed, by increasing the molecular weight of photoinitiators, their migratability within the polymer network can be drastically reduced. These dyes also possess an extended conjugation compared to mono-chalcones; thus, these photosensitizers can transfer an electron towards an electron acceptor more easily in the excited state.

2. The Different Synthetic Routes to bis-Chalcones

Bis-chalcones have recently been studied as photoinitiators of polymerization, and three different strategies have been developed to provide access to these structures. Notably, chalcones can be easily obtained by means of a Claisen-Schmidt condensation between an aldehyde and an acetophenone, in accordance with the reaction depicted in Scheme 1 [185][186][187][188][189][190][191][192][193][194]. No major differences can be found from the synthetic viewpoint between mono- and bis-chalcones, except that two equivalents of aldehydes have to be used in the case of bis-chalcones, comprising a central cyclic ketone. In addition to this first strategy based on cyclic ketones, a second approach can consist of connecting two mono-chalcones together. In this aim, two connected aldehydes or two connected acetophenones can be used to form bis-chalcones.
Scheme 1. Synthetic routes to mono- and bis-chalcones; and bis-chalcones obtained by connecting two mono-chalcones.
Based on the synthetic approach used to provide access to these structures, numerous modifications of the chalcone scaffold can be envisioned, such as a modification of the peripheral groups, the substitution pattern of the central cyclic aliphatic ketone, or the spacer introduced between the central core and the peripheral groups (see Figure 4). In the same spirit, bis-chalcones can be obtained via the condensation of acetophenones on bis-aldehydes. Aldehydes can also be condensed onto bis-acetophenones. Here, again, this strategy is highly versatile; since the spacer is used to connect the two chalcones, the substitution pattern of the chalcones can be easily tuned. Overall, the connection of two chalcones together enables a similar effect on the migratability of these macrophotoinitiators.
Figure 4. The different chemical modifications enabling the efficient tuning of the absorption spectra of bis-chalcones.

References

  1. Hatton, F.L. Recent advances in RAFT polymerization of monomers derived from renewable resources. Polym. Chem. 2020, 11, 220–229.
  2. Nothling, M.D.; Fu, Q.; Reyhani, A.; Allison-Logan, S.; Jung, K.; Zhu, J.; Kamigaito, M.; Boyer, C.; Qiao, G.G. Progress and Perspectives Beyond Traditional RAFT Polymerization. Adv. Sci. 2020, 7, 2001656.
  3. Tian, X.; Ding, J.; Zhang, B.; Qiu, F.; Zhuang, X.; Chen, Y. Recent Advances in RAFT Polymerization: Novel Initiation Mechanisms and Optoelectronic Applications. Polymers 2018, 10, 318.
  4. Audran, G.; Bagryanskaya, E.G.; Marque, S.R.A.; Postnikov, P. New Variants of Nitroxide Mediated Polymerization. Polymers 2020, 12, 1481.
  5. Sciannamea, V.; Jérôme, R.; Detrembleur, C. In-Situ Nitroxide-Mediated Radical Polymerization (NMP) Processes: Their Understanding and Optimization. Chem. Rev. 2008, 108, 1104–1126.
  6. Audran, G.; Bagryanskaya, E.; Edeleva, M.; Marque, S.R.A.; Parkhomenko, D.; Tretyakov, E.; Zhivetyeva, S. Coordination-Initiated Nitroxide-Mediated Polymerization (CI-NMP). Aust. J. Chem. 2018, 71, 334–340.
  7. Shao, J.; Huang, Y.; Fan, Q. Visible light initiating systems for photopolymerization: Status, development and challenges. Polym. Chem. 2014, 5, 4195–4210.
  8. Park, H.K.; Shin, M.; Kim, B.; Park, J.W.; Lee, H. A visible light-curable yet visible wavelength-transparent resin for stereolithography 3D printing. NPG Asia Mater. 2018, 10, 82–89.
  9. Yoshino, F.; Yoshida, A. Effects of blue-light irradiation during dental treatment. Jpn. Dent. Sci. Rev. 2018, 54, 160–168.
  10. Garra, P.; Dietlin, C.; Morlet-Savary, F.; Dumur, F.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Redox two-component initiated free radical and cationic polymerizations: Concepts, reactions and applications. Prog. Polym. Sci. 2019, 94, 33–56.
  11. Fouassier, J.-P.; Allonas, X.; Burget, D. Photopolymerization reactions under visible lights: Principle, mechanisms and examples of applications. Prog. Org. Coat. 2003, 47, 16–36.
  12. Fiedor, P.; Pilch, M.; Szymaszek, P.; Chachaj-Brekiesz, A.; Galek, M.; Orty, J. Photochemical Study of a New Bimolecular Photoinitiating System for Vat Photopolymerization 3D Printing Techniques under Visible Light. Catalysts 2020, 10, 284.
  13. Mendes-Felipe, C.; Oliveira, J.; Etxebarria, I.; Vilas-Vilela, J.L.; Lanceros-Mendez, S. State-of-the-art and future challenges of UV curable polymer-based smart materials for printing technologies. Adv. Mater. Technol. 2019, 4, 1800618.
  14. Shukla, V.; Bajpai, M.; Singh, D.K.; Singh, M.; Shukla, R. Review of basic chemistry of UV-curing technology. Pigm. Resin Technol. 2004, 33, 272–279.
  15. Chen, M.; Zhong, M.; Johnson, J.A. Light-controlled radical polymerization: Mechanisms, methods, and applications. Chem. Rev. 2016, 116, 10167–10211.
  16. Crivello, J.V.; Reichmanis, E. Photopolymer materials and processes for advanced technologies. Chem. Mater. 2014, 26, 533–548.
  17. Bonardi, A.-H.; Dumur, F.; Grant, T.M.; Noirbent, G.; Gigmes, D.; Lessard, B.H.; Fouassier, J.-P.; Lalevée, J. High performance near infrared (NIR) photoinitiating systems operating under low light intensity and in presence of oxygen. Macromolecules 2018, 51, 1314–1324.
  18. Scanone, A.C.; Casado, U.; Schroeder, W.F.; Hoppe, C.E. Visible-light photopolymerization of epoxy-terminated poly(dimethylsiloxane) blends: Influence of the cycloaliphatic monomer content on the curing behavior and network properties. Eur. Polym. J. 2020, 134, 109841.
  19. Garra, P.; Bonardi, A.-H.; Baralle, A.; Al Mousawi, A.; Bonardi, F.; Dietlin, C.; Morlet-Savary, F.; Fouassier, J.-P.; Lalevée, J. Monitoring photopolymerization reactions through thermal imaging: A unique tool for the real-time follow-up of thick samples, 3D Printing, and composites. J. Polym. Sci. A Polym. Chem. 2018, 56, 889–899.
  20. Sun, K.; Pigot, C.; Chen, H.; Nechab, M.; Gigmes, D.; Morlet-Savary, F.; Graff, B.; Liu, S.; Xiao, P.; Dumur, F.; et al. Free radical photopolymerization and 3D printing using newly developed dyes: Indane-1,3-dione and 1H-cyclopentanaphthalene-1,3-dione derivatives as photoinitiators in three-component systems. Catalysts 2020, 10, 463.
  21. Lalevée, J.; Mokbel, H.; Fouassier, J.-P. Recent developments of versatile photoinitiating systems for cationic ring opening polymerization operating at any wavelengths and under low light intensity sources. Molecules 2015, 20, 7201–7221.
  22. Tehfe, M.-A.; Louradour, F.; Lalevée, J.; Fouassier, J.-P. Photopolymerization reactions: On the way to a green and sustainable chemistry. Appl. Sci. 2013, 3, 490–514.
  23. Podsiadły, R.; Maruszewska, A.; Michalski, R.; Marcinek, A.; Kolinska, J. Naphthoylene benzimidazolone dyes as electron transfer photosensitizers for iodonium salt induced cationic photopolymerizations. Dyes Pigm. 2012, 95, 252–259.
  24. Zhang, Z.; Corrigan, N.; Bagheri, A.; Jin, J.; Boyer, C. A versatile 3D and 4D printing system through photocontrolled raft polymerization. Angew. Chem. 2019, 131, 18122–18131.
  25. Bagheri, A.; Engel, K.A.; Anderson Bainbridge, C.W.; Xu, J.; Boyer, C.; Jin, J. 3D printing of polymeric materials based on photo-RAFT polymerization. Polym. Chem. 2020, 11, 641–647.
  26. Bagheri, A.; Jin, J. Photopolymerization in 3D Printing. ACS Appl. Polym. Mater. 2019, 1, 593–611.
  27. Aduba, D.C., Jr.; Margaretta, E.D.; Marnot, A.E.C.; Heifferon, K.V.; Surbey, W.R.; Chartrain, N.A.; Whittington, A.R.; Long, T.E.; Williams, C.B. Vat photopolymerization 3D printing of acid-cleavable PEG-methacrylate networks for biomaterial applications. Mater. Today Commun. 2019, 19, 204–211.
  28. Lin, J.-T.; Cheng, D.-C.; Chen, K.-T.; Liu, H.-W. Dual-wavelength (UV and blue) controlled photopolymerization confinement for 3D-printing: Modeling and analysis of measurements. Polymers 2019, 11, 1819.
  29. Jasinski, F.; Zetterlund, P.B.; Braun, A.M.; Chemtob, A. Photopolymerization in dispersed systems. Prog. Polym. Sci. 2018, 84, 47–88.
  30. Noè, C.; Hakkarainen, M.; Sangermano, M. Cationic UV-Curing of Epoxidized Biobased Resins. Polymers 2021, 13, 89.
  31. Yuan, Y.; Li, C.; Zhang, R.; Liu, R.; Liu, J. Low volume shrinkage photopolymerization system using hydrogen-bond-based monomers. Prog. Org. Coat. 2019, 137, 105308.
  32. Khudyakov, I.V.; Legg, J.C.; Purvis, M.B.; Overton, B.J. Kinetics of Photopolymerization of Acrylates with Functionality of 1-6. Ind. Eng. Chem. Res. 1999, 38, 3353–3359.
  33. Noirbent, G.; Dumur, F. Photoinitiators of polymerization with reduced environmental impact: Nature as an unlimited and renewable source of dyes. Eur. Polym. J. 2021, 142, 110109.
  34. Zhao, H.; Sha, J.; Wang, X.; Jiang, Y.; Chen, T.; Wu, T.; Chen, X.; Ji, H.; Gao, Y.; Xie, L.; et al. Spatiotemporal control of polymer brush formation through photoinduced radical polymerization regulated by DMD light modulation. Lab Chip 2019, 19, 2651–2662.
  35. Xi, W.; Peng, H.; Aguirre-Soto, A.; Kloxin, C.J.; Stansbury, J.W.; Bowman, C.N. Spatial and Temporal Control of Thiol-Michael Addition via Photocaged Superbase in Photopatterning and Two-Stage Polymer Networks Formation. Macromolecules 2014, 47, 6159–6165.
  36. Tehfe, M.-A.; Dumur, F.; Contal, E.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Novel highly efficient organophotocatalysts: Truxene-acridine-1,8-diones as photoinitiators of polymerization. Macromol. Chem. Phys. 2013, 214, 2189–2201.
  37. Xiao, P.; Dumur, F.; Tehfe, M.-A.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Difunctional acridinediones as photoinitiators of polymerization under UV and visible lights: Structural effects. Polymer 2013, 54, 3458–3466.
  38. Xiao, P.; Dumur, F.; Tehfe, M.-A.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Acridinediones: Effect of substituents on their photoinitiating abilities in radical and cationic photopolymerization. Macromol. Chem. Phys. 2013, 214, 2276–2282.
  39. Zhang, J.; Campolo, D.; Dumur, F.; Xiao, P.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. The carbazole-bound ferrocenium salt as a specific cationic photoinitiator upon near-UV and visible LEDs (365–405 nm). Polym. Bull. 2016, 73, 493–507.
  40. Al Mousawi, A.; Dumur, F.; Toufaily, J.; Hamieh, T.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Carbazole scaffold based photoinitiators/photoredox catalysts for new LED projector 3D printing resins. Macromolecules 2017, 50, 2747–2758.
  41. Al Mousawi, A.; Magaldi Lara, D.; Noirbent, G.; Dumur, F.; Toufaily, J.; Hamieh, T.; Bui, T.-T.; Goubard, F.; Graff, B.; Gigmes, D.; et al. Carbazole derivatives with thermally activated delayed fluorescence property as photoinitiators/photoredox catalysts for LED 3D printing technology. Macromolecules 2017, 50, 4913–4926.
  42. Al Mousawi, A.; Garra, P.; Dumur, F.; Bui, T.-T.; Goubard, F.; Toufaily, J.; Hamieh, T.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; et al. Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing. Molecules 2018, 22, 2143.
  43. Al Mousawi, A.; Arar, A.; Ibrahim-Ouali, M.; Duval, S.; Dumur, F.; Garra, P.; Toufaily, J.; Hamieh, T.; Graff, B.; Gigmes, D.; et al. Carbazole-based compounds as photoinitiators for free radical and cationic polymerization upon near visible light illumination. Photochem. Photobiol. Sci. 2018, 17, 578–585.
  44. Abdallah, M.; Magaldi, D.; Hijazi, A.; Graff, B.; Dumur, F.; Fouassier, J.-P.; Bui, T.-T.; Goubard, F.; Lalevée, J. Development of new high performance visible light photoinitiators based on carbazole scaffold and their applications in 3D printing and photocomposite synthesis. J. Polym. Sci. A Polym. Chem. 2019, 57, 2081–2092.
  45. Tehfe, M.-A.; Dumur, F.; Contal, E.; Graff, B.; Gigmes, D.; Morlet-Savary, F.; Fouassier, J.-P.; Lalevée, J. New insights in radical and cationic polymerizations upon visible light exposure: Role of novel photoinitiator systems based on the pyrene chromophore. Polym. Chem. 2013, 4, 1625–1634.
  46. Telitel, S.; Dumur, F.; Faury, T.; Graff, B.; Tehfe, M.-A.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. New core-pyrene π-structure organophotocatalysts usable as highly efficient photoinitiators. Beilstein J. Org. Chem. 2013, 9, 877–890.
  47. Uchida, N.; Nakano, H.; Igarashi, T.; Sakurai, T. Nonsalt 1-(arylmethyloxy)pyrene photoinitiators capable of initiating cationic polymerization. J. Appl. Polym. Sci. 2014, 131, 40510.
  48. Mishra, A.; Daswal, S. 1-(Bromoacetyl)pyrene, a novel photoinitiator for the copolymerization of styrene and methylmethacrylate. Rad. Phys. Chem. 2006, 75, 1093–1100.
  49. Tehfe, M.-A.; Dumur, F.; Graff, B.; Morlet-Savary, F.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Design of new Type I & Type II photoinitiators possessing highly coupled pyrene-ketone moieties. Polym. Chem. 2013, 4, 2313–2324.
  50. Dumur, F. Recent advances on pyrene-based photoinitiators of polymerization. Eur. Polym. J. 2020, 126, 109564.
  51. Lalevée, J.; Peter, M.; Dumur, F.; Gigmes, D.; Blanchard, N.; Tehfe, M.-A.; Morlet-Savary, F.; Fouassier, J.-P. Subtle ligand effects in oxidative photocatalysis with iridium complexes: Application to photopolymerization. Chem. Eur. J. 2011, 17, 15027–15031.
  52. Lalevée, J.; Tehfe, M.-A.; Dumur, F.; Gigmes, D.; Blanchard, N.; Morlet-Savary, F.; Fouassier, J.-P. Iridium photocatalysts in free radical photopolymerization under visible lights. ACS Macro Lett. 2012, 1, 286–290.
  53. Lalevée, J.; Dumur, F.; Mayer, C.R.; Gigmes, D.; Nasr, G.; Tehfe, M.-A.; Telitel, S.; Morlet-Savary, F.; Graff, B.; Fouassier, J.-P. Photopolymerization of N-vinylcarbazole using visible-light harvesting iridium complexes as photoinitiators. Macromolecules 2012, 45, 4134–4141.
  54. Telitel, S.; Dumur, F.; Telitel, S.; Soppera, O.; Lepeltier, M.; Guillaneuf, Y.; Poly, J.; Morlet-Savary, F.; Fioux, P.; Fouassier, J.-P.; et al. Photoredox catalysis using a new iridium complex as an efficient toolbox for radical, cationic and controlled polymerizations under soft blue to green lights. Polym. Chem. 2015, 6, 613–624.
  55. Telitel, S.; Dumur, F.; Lepeltier, M.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Photoredox process induced polymerization reactions: Iridium complexes for panchromatic photo-initiating systems. C. R. Chim. 2016, 19, 71–78.
  56. Tehfe, M.-A.; Lepeltier, M.; Dumur, F.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Structural effects in the iridium complex series: Photoredox catalysis and photoinitiation of polymerization reactions under visible lights. Macromol. Chem. Phys. 2017, 218, 1700192.
  57. Dumur, F.; Nasr, G.; Wantz, G.; Mayer, C.R.; Dumas, E.; Guerlin, A.; Miomandre, F.; Clavier, G.; Bertin, D.; Gigmes, D. Cationic iridium complex for the design of soft salt-based phosphorescent OLEDs and color-tunable Light-Emitting Electrochemical Cells. Org. Electron. 2011, 12, 1683–1694.
  58. Nasr, G.; Guerlin, A.; Dumur, F.; Beouch, L.; Dumas, E.; Clavier, G.; Miomandre, F.; Goubard, F.; Gigmes, D.; Bertin, D.; et al. Iridium (III) soft salts from dinuclear cationic and mononuclear anionic complexes for OLEDs devices. Chem. Commun. 2011, 47, 10698–10700.
  59. Dumur, F.; Bertin, D.; Gigmes, D. Iridium (III) complexes as promising emitters for solid-state light-emitting electrochemical cells (LECs). Int. J. Nanotechnol. 2012, 9, 377–395.
  60. Xiao, P.; Dumur, F.; Zhang, J.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. Copper complexes in radical photoinitiating systems: Applications to free radical and cationic polymerization under visible lights. Macromolecules 2014, 47, 3837–3844.
  61. Xiao, P.; Dumur, F.; Zhang, J.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Copper complexes: The effect of ligands on their photoinitiation efficiencies in radical polymerization reactions under visible light. Polym. Chem. 2014, 5, 6350–6357.
  62. Xiao, P.; Zhang, J.; Campolo, D.; Dumur, F.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Copper and iron complexes as visible-light-sensitive photoinitiators of polymerization. J. Polym. Sci. A Polym. Chem. 2015, 53, 2673–2684.
  63. Al Mousawi, A.; Kermagoret, A.; Versace, D.-L.; Toufaily, J.; Hamieh, T.; Graff, B.; Dumur, F.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Copper photoredox catalysts for polymerization upon near UV or visible light: Structure/reactivity/ efficiency relationships and use in LED projector 3D printing resins. Polym. Chem. 2017, 8, 568–580.
  64. Garra, P.; Kermagoret, A.; Al Mousawi, A.; Dumur, F.; Gigmes, D.; Morlet-Savary, F.; Dietlin, C.; Fouassier, J.-P.; Lalevée, J. New copper(I) complex based initiating systems in redox polymerization and comparison with the amine/benzoyl peroxide reference. Polym. Chem. 2017, 8, 4088–4097.
  65. Garra, P.; Dumur, F.; Morlet-Savary, F.; Dietlin, C.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Mechanosynthesis of a copper complex for redox initiating systems with a unique near infrared light activation. J. Polym. Sci. A Polym. Chem. 2017, 55, 3646–3655.
  66. Mokbel, H.; Anderson, D.; Plenderleith, R.; Dietlin, C.; Morlet-Savary, F.; Dumur, F.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Copper PhotoRedox Catalyst “G1”: A New High Performance Photoinitiator for Near-UV and Visible LEDs. Polym. Chem. 2017, 8, 5580–5592.
  67. Garra, P.; Dumur, F.; Al Mousawi, A.; Graff, B.; Gigmes, D.; Morlet-Savary, F.; Dietlin, C.; Fouassier, J.-P.; Lalevée, J. Mechanosynthesized Copper (I) complex based initiating systems for redox polymerization: Towards upgraded oxidizing and reducing agents. Polym. Chem. 2017, 8, 5884–5896.
  68. Garra, P.; Carré, M.; Dumur, F.; Morlet-Savary, F.; Dietlin, C.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Copper-based (photo) redox initiating systems as highly efficient systems for interpenetrating polymer network preparation. Macromolecules 2018, 51, 679–688.
  69. Garra, P.; Dumur, F.; Nechab, M.; Morlet-Savary, F.; Dietlin, C.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Stable copper acetylacetonate-based oxidizing agents in redox (NIR photoactivated) polymerization: An opportunity for one pot grafting from approach and example on a 3D printed object. Polym. Chem. 2018, 9, 2173–2182.
  70. Mokbel, H.; Anderson, D.; Plenderleith, R.; Dietlin, C.; Morlet-Savary, F.; Dumur, F.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Simultaneous initiation of radical and cationic polymerization reactions using the “G1” copper complex as photoRedox catalyst: Applications of free radical/cationic hybrid photo-polymerization in the composites and 3D printing fields. Prog. Org. Coat. 2019, 132, 50–61.
  71. Launay, V.; Caron, A.; Noirbent, G.; Gigmes, D.; Dumur, F.; Lalevée, J. NIR dyes as innovative tools for reprocessing/recycling of plastics: Benefits of the photothermal activation in the near-infrared range. Adv. Funct. Mater. 2021, 31, 2006324.
  72. Bonardi, A.; Bonardi, F.; Noirbent, G.; Dumur, F.; Dietlin, C.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Different NIR dye scaffolds for polymerization reactions under NIR light. Polym. Chem. 2019, 10, 6505–6514.
  73. Giacoletto, N.; Ibrahim-Ouali, M.; Dumur, F. Recent advances on squaraine-based photoinitiators of polymerization. Eur. Polym. J. 2021, 150, 110427.
  74. Kamoun, E.A.; Winkel, A.; Eisenburger, M.; Menzel, H. Carboxylated camphorquinone as visible-light photoinitiator for biomedical application: Synthesis, characterization, and application. Arab. J. Chem. 2016, 9, 745–754.
  75. Santini, A.; Gallegos, I.T.; Felix, C.M. Photoinitiators in dentistry: A review. Prim. Dent. J. 2013, 2, 30–33.
  76. Xiao, P.; Dumur, F.; Frigoli, M.; Graff, B.; Morlet-Savary, F.; Wantz, G.; Bock, H.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. Perylene derivatives as photoinitiators in blue light sensitive cationic or radical curable films and panchromatic thiol-ene polymerizable films. Eur. Polym. J. 2014, 53, 215–222.
  77. Tehfe, M.-A.; Dumur, F.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Green light induced cationic ring opening polymerization reactions: Perylene-3,4:9,10-bis(dicarboximide) as efficient photosensitizers. Macromol. Chem. Phys. 2013, 214, 1052–1060.
  78. Xiao, P.; Dumur, F.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Red-light-induced cationic photopolymerization: Perylene derivatives as efficient photoinitiators. Macromol. Rapid Commun. 2013, 34, 1452–1458.
  79. Mokbel, H.; Toufaily, J.; Hamieh, T.; Dumur, F.; Campolo, D.; Gigmes, D.; Fouassier, J.-P.; Ortyl, J.; Lalevee, J. Specific cationic photoinitiators for Near UV and visible LEDs: Iodonium vs. ferrocenium structures. J. Appl. Polym. Sci. 2015, 132, 42759.
  80. Villotte, S.; Gigmes, D.; Dumur, F.; Lalevée, J. Design of Iodonium Salts for UV or Near-UV LEDs for Photoacid Generator and Polymerization Purposes. Molecules 2020, 25, 149.
  81. Zivic, N.; Bouzrati-Zerrelli, M.; Villotte, S.; Morlet-Savary, F.; Dietlin, C.; Dumur, F.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. A novel naphthalimide scaffold based iodonium salt as a one-component photoacid/photoinitiator for cationic and radical polymerization under LED exposure. Polym. Chem. 2016, 7, 5873–5879.
  82. Liu, S.; Chen, H.; Zhang, Y.; Sun, K.; Xu, Y.; Morlet-Savary, F.; Graff, B.; Noirbent, G.; Pigot, C.; Brunel, D.; et al. Monocomponent photoinitiators based on benzophenone-carbazole structure for led photoinitiating systems and application on 3D printing. Polymers 2020, 12, 1394.
  83. Xiao, P.; Dumur, F.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Variations on the benzophenone skeleton: Novel high-performance blue light sensitive photoinitiating systems. Macromolecules 2013, 46, 7661–7667.
  84. Zhang, J.; Frigoli, M.; Dumur, F.; Xiao, P.; Ronchi, L.; Graff, B.; Morlet-Savary, F.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. Design of novel photoinitiators for radical and cationic photopolymerizations under Near UV and Visible LEDs (385, 395 and 405 nm). Macromolecules 2014, 47, 2811–2819.
  85. Liu, S.; Brunel, D.; Noirbent, G.; Mau, A.; Chen, H.; Morlet-Savary, F.; Graff, B.; Gigmes, D.; Xiao, P.; Dumur, F.; et al. New multifunctional benzophenone-based photoinitiators with high migration stability and their application in 3D printing. Mater. Chem. Front. 2021, 5, 1982–1994.
  86. Liu, S.; Brunel, D.; Sun, K.; Zhang, Y.; Chen, H.; Xiao, P.; Dumur, F.; Lalevée, J. Novel photoinitiators based on benzophenone-triphenylamine hybrid structure for led photopolymerization. Macromol. Rapid Commun. 2020, 41, 2000460.
  87. Liu, S.; Brunel, D.; Sun, K.; Xu, Y.; Morlet-Savary, F.; Graff, B.; Xiao, P.; Dumur, F.; Lalevée, J. A mono-component bifunctional benzophenone-carbazole type II photoinitiator for led photoinitiating systems. Polym. Chem. 2020, 11, 3551–3556.
  88. Mokbel, H.; Dumur, F.; Lalevée, J. On demand NIR activated photopolyaddition reactions. Polym. Chem. 2020, 11, 4250–4259.
  89. Mokbel, H.; Graff, B.; Dumur, F.; Lalevée, J. NIR sensitizer operating under long wavelength (1064 nm) for free radical photopolymerization processes. Macromol. Rapid Commun. 2020, 41, 2000289.
  90. Zhang, J.; Zivic, N.; Dumur, F.; Guo, C.; Li, Y.; Xiao, P.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Panchromatic photoinitiators for radical, cationic and thiol-ene polymerization reactions: A search in the diketopyrrolopyrrole or indigo dye series. Mater. Today Commun. 2015, 4, 101–108.
  91. Xiao, P.; Hong, W.; Li, Y.; Dumur, F.; Graff, B.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. Diketopyrrolopyrrole dyes: Structure/reactivity/efficiency relationship in photoinitiating systems upon visible lights. Polymer 2014, 55, 746–751.
  92. Xiao, P.; Hong, W.; Li, Y.; Dumur, F.; Graff, B.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. Green light sensitive diketopyrrolopyrrole derivatives used in versatile photoinitiating systems for photopolymerizations. Polym. Chem. 2014, 5, 2293–2300.
  93. Al Mousawi, A.; Dumur, F.; Garra, P.; Toufaily, J.; Hamieh, T.; Goubard, F.; Bui, T.-T.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; et al. Azahelicenes as visible light photoinitiators for cationic and radical polymerization: Preparation of photo-luminescent polymers and use in high performance LED projector 3D printing resins. J. Polym. Sci. A Polym. Chem. 2017, 55, 1189–1199.
  94. Al Mousawi, A.; Schmitt, M.; Dumur, F.; Ouyang, J.; Favereaud, L.; Dorcet, V.; Vanthuyne, N.; Garra, P.; Toufaily, J.; Hamieh, T.; et al. Visible light chiral photoinitiator for radical polymerization and synthesis of polymeric films with strong chiroptical activity. Macromolecules 2018, 51, 5628–5637.
  95. Bonardi, A.-H.; Zahouily, S.; Dietlin, C.; Graff, B.; Morlet-Savary, F.; Ibrahim-Ouali, M.; Gigmes, D.; Hoffmann, N.; Dumur, F.; Lalevée, J. New 1,8-naphthalimide derivatives as photoinitiators for free radical polymerization upon visible light. Catalysts 2019, 9, 637.
  96. Zhang, J.; Zivic, N.; Dumur, F.; Xiao, P.; Graff, B.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. Naphthalimide-tertiary amine derivatives as blue-light-sensitive photoinitiators. ChemPhotoChem 2018, 2, 481–489.
  97. Xiao, P.; Dumur, F.; Zhang, J.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Naphthalimide derivatives: Substituent effects on the photoinitiating ability in polymerizations under near UV, purple, white and blue LEDs (385 nm, 395 nm, 405 nm, 455 nm or 470 nm). Macromol. Chem. Phys. 2015, 216, 1782–1790.
  98. Xiao, P.; Dumur, F.; Zhang, J.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Naphthalimide-phthalimide derivative based photoinitiating systems for polymerization reactions under blue lights. J. Polym. Sci. A Polym. Chem. 2015, 53, 665–674.
  99. Zhang, J.; Zivic, N.; Dumur, F.; Xiao, P.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. A benzophenone-naphthalimide derivative as versatile photoinitiator for near UV and visible lights. J. Polym. Sci. A Polym. Chem. 2015, 53, 445–451.
  100. Zhang, J.; Zivic, N.; Dumur, F.; Xiao, P.; Graff, B.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. N-[2-(dimethylamino)ethyl]-1,8-naphthalimide derivatives as photoinitiators under LEDs. Polym. Chem. 2018, 9, 994–1003.
  101. Zivic, N.; Zhang, J.; Bardelang, D.; Dumur, F.; Xiao, P.; Jet, T.; Versace, D.-L.; Dietlin, C.; Morlet-Savary, F.; Graff, B.; et al. Novel naphthalimideamine based photoinitiators operating under violet and blue LEDs and usable for various polymerization reactions and synthesis of hydrogels. Polym. Chem. 2016, 7, 418–429.
  102. Zhang, J.; Dumur, F.; Xiao, P.; Graff, B.; Bardelang, D.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Structure design of naphthalimide derivatives: Towards versatile photo-initiators for near UV/Visible LEDs, 3D printing and water-soluble photoinitiating systems. Macromolecules 2015, 48, 2054–2063.
  103. Zhang, J.; Zivic, N.; Dumur, F.; Xiao, P.; Graff, B.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. UV violet-blue LED induced polymerizations: Specific photoinitiating systems at 365, 385, 395 and 405 nm. Polymer 2014, 55, 6641–6648.
  104. Xiao, P.; Dumur, F.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Blue light sensitive dyes for various photopolymerization reactions: Naphthalimide and naphthalic anhydride derivatives. Macromolecules 2014, 47, 601–608.
  105. Xiao, P.; Dumur, F.; Frigoli, M.; Tehfe, M.-A.; Graff, B.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. Naphthalimide based methacrylated photoinitiators in radical and cationic photopolymerization under visible light. Polym. Chem. 2013, 4, 5440–5448.
  106. Noirbent, G.; Dumur, F. Recent advances on naphthalic anhydrides and 1,8-naphthalimide-based photoinitiators of polymerization. Eur. Polym. J. 2020, 132, 109702.
  107. Rahal, M.; Mokbel, H.; Graff, B.; Pertici, V.; Gigmes, D.; Toufaily, J.; Hamieh, T.; Dumur, F.; Lalevée, J. Naphthalimide-Based dyes as photoinitiators under visible light irradiation and their applications: Photocomposite synthesis, 3D printing and polymerization in water. ChemPhotoChem 2021, 5, 476–490.
  108. Chen, H.; Noirbent, G.; Sun, K.; Brunel, D.; Gigmes, D.; Morlet-Savary, F.; Zhang, Y.; Liu, S.; Xiao, P.; Dumur, F.; et al. Photoinitiators derived from natural product scaffolds: Mono-chalcones in three-component photoinitiating systems and their applications in 3D printing. Polym. Chem. 2020, 11, 4647–4659.
  109. Tang, L.; Nie, J.; Zhu, X. A high-performance phenyl-free LED photoinitiator for cationic or hybrid photopolymerization and its application in LED cationic 3D printing. Polym. Chem. 2020, 11, 2855–2863.
  110. Xu, Y.; Noirbent, G.; Brunel, D.; Ding, Z.; Gigmes, D.; Graff, B.; Xiao, P.; Dumur, F.; Lalevée, J. Allyloxy ketones as efficient photoinitiators with high migration stability in free radical polymerization and 3D printing. Dyes Pigm. 2021, 185, 108900.
  111. Sun, K.; Chen, H.; Zhang, Y.; Morlet-Savary, F.; Graff, B.; Xiao, P.; Dumur, F.; Lalevée, J. High-performance sunlight induced polymerization using novel push-pull dyes with high light absorption properties. Eur. Polym. J. 2021, 151, 110410.
  112. Chen, H.; Noirbent, G.; Liu, S.; Brunel, D.; Graff, B.; Gigmes, D.; Zhang, Y.; Sun, K.; Morlet-Savary, F.; Xiao, P.; et al. Bis-chalcone derivatives derived from natural products as near-UV/visible light sensitive photoinitiators for 3D/4D printing. Mater. Chem. Front. 2021, 5, 901–916.
  113. Xu, Y.; Ding, Z.; Zhu, H.; Graff, B.; Xiao, P.; Dumur, F.; Lalevée, F. Design of ketone derivatives as highly efficient photoinitiators for free radical and cationic photopolymerizations and application in 3D printing of composites. J. Polym. Sci. 2021.
  114. Liu, S.; Zhang, Y.; Sun, K.; Graff, B.; Xiao, P.; Dumur, F.; Lalevée, J. Design of photoinitiating systems based on the chalcone-anthracene scaffold for led cationic photopolymerization and application in 3D Printing. Eur. Polym. J. 2021, 147, 110300.
  115. Zhang, J.; Campolo, D.; Dumur, F.; Xiao, P.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. Iron complexes as photoinitiators for radical and cationic polymerization through photoredox catalysis processes. J. Polym. Sci. A Polym. Chem. 2015, 53, 42–49.
  116. Telitel, S.; Dumur, F.; Campolo, D.; Poly, J.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Iron complexes as potential photocatalysts for controlled radical photopolymerizations: A tool for modifications and patterning of surfaces. J. Polym. Sci. A Polym. Chem. 2016, 54, 702–713.
  117. Zhang, J.; Campolo, D.; Dumur, F.; Xiao, P.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. Visible-light-sensitive photoredox catalysis by iron complexes: Applications in cationic and radical polymerization reactions. J. Polym. Sci. A Polym. Chem. 2016, 54, 2247–2253.
  118. Zhang, J.; Campolo, D.; Dumur, F.; Xiao, P.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. Novel iron complexes in visible-light-sensitive photoredox catalysis: Effect of ligands on their photoinitiation efficiencies. ChemCatChem 2016, 8, 2227–2233.
  119. Zhang, J.; Dumur, F.; Horcajada, P.; Livage, C.; Xiao, P.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. Iron-based metal-organic frameworks (MOF) as photocatalysts for radical and cationic polymerizations under near UV and visible LEDs (385–405 nm). Macromol. Chem. Phys. 2016, 217, 2534–2540.
  120. Dumur, F. Recent advances on ferrocene-based photoinitiating systems. Eur. Polym. J. 2021, 147, 110328.
  121. Tehfe, M.-A.; Dumur, F.; Xiao, P.; Graff, B.; Morlet-Savary, F.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. New chromone based photoinitiators for polymerization reactions upon visible lights. Polym. Chem. 2013, 4, 4234–4244.
  122. You, J.; Fu, H.; Zhao, D.; Hu, T.; Nie, J.; Wang, T. Flavonol dyes with different substituents in photopolymerization. J. Photochem. Photobiol. A Chem. 2020, 386, 112097.
  123. Al Mousawi, A.; Garra, P.; Schmitt, M.; Toufaily, J.; Hamieh, T.; Graff, B.; Fouassier, J.-P.; Dumur, F.; Lalevée, J. 3-Hydroxyflavone and N-phenyl-glycine in high performance photo-initiating systems for 3D printing and photocomposites synthesis. Macromolecules 2018, 51, 4633–4641.
  124. Karaca, N.; Ocala, N.; Arsua, N.; Jockusch, S. Thioxanthone-benzothiophenes as photoinitiator for free radical polymerization. J. Photochem. Photobiol. A Chem. 2016, 331, 22–28.
  125. Wu, Q.; Wang, X.; Xiong, Y.; Yang, J.; Tang, H. Thioxanthone based one-component polymerizable visible light photoinitiator for free radical polymerization. RSC Adv. 2016, 6, 66098–66107.
  126. Qiu, J.; Wei, J. Thioxanthone photoinitiator containing polymerizable N-aromatic maleimide for photopolymerization. J. Polym. Res. 2014, 21, 559.
  127. Dadashi-Silab, S.; Aydogan, C.; Yagci, Y. Shining a light on an adaptable photoinitiator: Advances in photopolymerizations initiated by thioxanthones. Polym. Chem. 2015, 6, 6595–6615.
  128. Zhang, J.; Lalevée, J.; Zhao, J.; Graff, B.; Stenzel, M.H.; Xiao, P. Dihydroxyanthraquinone derivatives: Natural dyes as blue-light-sensitive versatile photoinitiators of photopolymerization. Polym. Chem. 2016, 7, 7316–7324.
  129. Al Mousawi, A.; Poriel, C.; Dumur, F.; Toufaily, J.; Hamieh, T.; Fouassier, J.-P.; Lalevée, J. Zinc tetraphenylporphyrin as high performance visible-light photoinitiator of cationic photosensitive resins for LED projector 3D printing applications. Macromolecules 2017, 50, 746–753.
  130. Noirbent, G.; Xu, Y.; Bonardi, A.-H.; Gigmes, D.; Lalevée, J.; Dumur, F. Metalated Porphyrins as versatile visible light and NIR photoinitiators of polymerization. Eur. Polym. J. 2020, 139, 110019.
  131. Tehfe, M.-A.; Lalevée, J.; Dumur, F.; Telitel, S.; Gigmes, D.; Contal, E.; Bertin, D.; Fouassier, J.-P. Zinc-based metal complexes as new photocatalysts in polymerization initiating systems. Eur. Polym. J. 2013, 49, 1040–1049.
  132. Abdallah, M.; Le, H.; Hijazi, A.; Graff, B.; Dumur, F.; Bui, T.-T.; Goubard, F.; Fouassier, J.-P.; Lalevée, J. Acridone derivatives as high performance visible light photoinitiators for cationic and radical photosensitive resins for 3D printing technology and for low migration photopolymer property. Polymer 2018, 159, 47–58.
  133. Zhang, J.; Dumur, F.; Bouzrati, M.; Xiao, P.; Dietlin, C.; Morlet-Savary, F.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Novel panchromatic photopolymerizable matrices: N,N’-dibutyl-quinacridone as an efficient and versatile photoinitiator. J. Polym. Sci. A Polym. Chem. 2015, 53, 1719–1727.
  134. Tehfe, M.-A.; Zein-Fakih, A.; Lalevée, J.; Dumur, F.; Gigmes, D.; Graff, B.; Morlet-Savary, F.; Hamieh, T.; Fouassier, J.-P. New pyridinium salts as versatile compounds for dye sensitized photo-polymerization. Eur. Polym. J. 2013, 49, 567–574.
  135. Xiao, P.; Frigoli, M.; Dumur, F.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Julolidine or fluorenone based push-pull dyes for polymerization upon soft polychromatic visible light or green light. Macromolecules 2014, 47, 106–112.
  136. Tehfe, M.-A.; Dumur, F.; Graff, B.; Morlet-Savary, F.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. New push-pull dyes derived from Michler’s ketone for polymerization reactions upon visible lights. Macromolecules 2013, 46, 3761–3770.
  137. Mokbel, H.; Dumur, F.; Mayer, C.R.; Morlet-Savary, F.; Graff, B.; Gigmes, D.; Toufaily, J.; Hamieh, T.; Fouassier, J.-P.; Lalevée, J. End capped polyenic structures as visible light sensitive photoinitiators for polymerization of vinylethers. Dyes Pigm. 2014, 105, 121–129.
  138. Garra, P.; Brunel, D.; Noirbent, G.; Graff, B.; Morlet-Savary, F.; Dietlin, C.; Sidorkin, V.F.; Dumur, F.; Duché, D.; Gigmes, D.; et al. Ferrocene-based (photo)redox polymerization under long wavelengths. Polym. Chem. 2019, 10, 1431–1441.
  139. Telitel, S.; Dumur, F.; Kavalli, T.; Graff, B.; Morlet-Savary, F.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. The 1,3-bis(dicyanomethylidene)-indane skeleton as a (photo) initiator in thermal ring opening polymerization at RT and radical or cationic photopolymerization. RSC Adv. 2014, 4, 15930–15936.
  140. Mokbel, H.; Dumur, F.; Graff, B.; Mayer, C.R.; Gigmes, D.; Toufaily, J.; Hamieh, T.; Fouassier, J.-P.; Lalevée, J. Michler’s ketone as an interesting scaffold for the design of high-performance dyes in photoinitiating systems upon visible lights. Macromol. Chem. Phys. 2014, 215, 783–790.
  141. Sun, K.; Liu, S.; Pigot, S.; Brunel, D.; Graff, B.; Nechab, M.; Gigmes, D.; Morlet-Savary, F.; Zhang, Y.; Xiao, P.; et al. Novel push-pull dyes derived from 1H-cyclopenta[b]naphthalene-1,3(2H)-dione as versatile photoinitiators for photopolymerization and their related applications: 3D-printing and fabrication of photocomposites. Catalysts 2020, 10, 1196.
  142. Tehfe, M.-A.; Dumur, F.; Graff, B.; Morlet-Savary, F.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Push–pull (thio)barbituric acid derivatives in dye photosensitized radical and cationic polymerization reactions under 457/473 nm laser beams or blue LEDs. Polym. Chem. 2013, 4, 3866–3875.
  143. Dumur, F.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Organic Electronics: An El Dorado in the quest of new photoCatalysts as photoinitiators of polymerization. Acc. Chem. Res. 2016, 49, 1980–1989.
  144. Sun, K.; Liu, S.; Chen, H.; Morlet-Savary, F.; Graff, B.; Pigot, C.; Nechab, M.; Xiao, P.; Dumur, F.; Lalevée, J. N-ethylcarbazole-1-allylidene-based push-pull dyes as efficient light harvesting photoinitiators for sunlight induced polymerization. Eur. Polym. J. 2021, 147, 110331.
  145. Dumur, F. Recent advances on visible light photoinitiators of polymerization based on indane-1,3-dione and related derivatives. Eur. Polym. J. 2021, 143, 110178.
  146. Abdallah, M.; Bui, T.-T.; Goubard, F.; Theodosopoulou, D.; Dumur, F.; Hijazi, A.; Fouassier, J.-P.; Lalevée, J. Phenothiazine derivatives as photoredox catalysts for cationic and radical photosensitive resins for 3D printing technology and photocomposites synthesis. Polym. Chem. 2019, 10, 6145–6156.
  147. Abdallah, M.; Hijazi, A.; Graff, B.; Fouassier, J.-P.; Rodeghiero, G.; Gualandi, A.; Dumur, F.; Cozzi, P.G.; Lalevée, J. Coumarin derivatives as high performance visible light photoinitiators/photoredox catalysts for photosensitive resins for 3D printing technology, photopolymerization in water and photocomposites synthesis. Polym. Chem. 2019, 10, 872–884.
  148. Li, Z.; Zou, X.; Zhu, G.; Liu, X.; Liu, R. Coumarin-Based Oxime Esters: Photobleachable and Versatile Unimolecular Initiators for Acrylate and Thiol-Based Click Photopolymerization under Visible Light-Emitting Diode Light Irradiation. ACS Appl. Mater. Interf. 2018, 10, 16113–16123.
  149. Abdallah, M.; Dumur, F.; Hijazi, A.; Rodeghiero, G.; Gualandi, A.; Cozzi, P.G.; Lalevée, J. Keto-coumarin scaffold for photo-initiators for 3D printing and photo-composites. J. Polym. Sci. 2020, 58, 1115–1129.
  150. Abdallah, M.; Hijazi, A.; Dumur, F.; Lalevée, J. Coumarins as powerful photosensitizers for the cationic polymerization of epoxy-silicones under near-UV and visible light and applications for 3D printing technology. Molecules 2020, 25, 2063.
  151. Chen, Q.; Yang, Q.; Gao, P.; Chi, B.; Nie, J.; He, Y. Photopolymerization of coumarin-containing reversible photoresponsive materials based on wavelength selectivity. Ind. Eng. Chem. Res. 2019, 58, 2970–2975.
  152. Rahal, M.; Mokbel, H.; Graff, B.; Toufaily, J.; Hamieh, T.; Dumur, F.; Lalevée, J. Mono vs. difunctional coumarin as photoinitiators in photocomposite synthesis and 3D printing. Catalysts 2020, 10, 1202.
  153. Abdallah, M.; Hijazi, A.; Cozzi, P.G.; Gualandi, A.; Dumur, F.; Lalevée, J. Boron compounds as additives for the cationic polymerization using coumarin derivatives in epoxy-silicones. Macromol. Chem. Phys. 2021, 222, 2000404.
  154. Guit, J.; Tavares, M.B.L.; Hul, J.; Ye, C.; Loos, K.; Jager, J.; Folkersma, R.; Voet, V.S.D. Photopolymer Resins with Biobased Methacrylates Based on Soybean Oil for Stereolithography. ACS Appl. Polym. Mater. 2020, 2, 949–957.
  155. Xiao, P.; Dumur, F.; Thirion, D.; Fagour, S.; Vacher, S.; Sallenave, X.; Morlet-Savary, F.; Graff, B.; Fouassier, J.-P.; Gigmes, D.; et al. Multicolor photoinitiators for radical and cationic polymerization: Mono vs. poly functional thiophene derivatives. Macromolecules 2013, 46, 6786–6793.
  156. Li, J.; Zhang, X.; Ali, S.; Akram, M.Y.; Nie, J.; Zhu, X. The effect of polyethylene glycoldiacrylate complexation on type II photoinitiator and promotion for visible light initiation system. J. Photochem. Photobiol. A Chem. 2019, 384, 112037.
  157. Li, J.; Li, S.; Li, Y.; Li, R.; Nie, J.; Zhu, X. In situ monitoring of photopolymerization by photoinitiator with luminescence characteristics. J. Photochem. Photobiol. A Chem. 2020, 389, 112225.
  158. Li, J.; Hao, Y.; Zhong, M.; Tang, L.; Nie, J.; Zhu, X. Synthesis of furan derivative as LED light photoinitiator: One-pot, low usage, photobleaching for light color 3D printing. Dyes Pigm. 2019, 165, 467–473.
  159. Xu, Y.; Noirbent, G.; Brunel, D.; Ding, Z.; Gigmes, D.; Graff, B.; Xiao, P.; Dumur, F.; Lalevée, J. Novel ketone derivatives based photoinitiating systems for free radical polymerization under mild conditions and 3D printing. Polym. Chem. 2020, 11, 5767–5777.
  160. Arikawa, H.; Takahashi, H.; Kanie, T.; Ban, S. Effect of various visible light photoinitiators on the polymerization and color of light-activated resins. Dent. Mater. J. 2009, 28, 454–460.
  161. Tomal, W.; Ortyl, J. Water-Soluble Photoinitiators in Biomedical Applications. Polymers 2020, 12, 1073.
  162. Tehfe, M.-A.; Dumur, F.; Graff, B.; Clément, J.-L.; Gigmes, D.; Morlet-Savary, F.; Fouassier, J.-P.; Lalevée, J. New Cleavable Photoinitiator Architecture with Huge Molar Extinction Coefficients for Polymerization in the 340−450 nm Range. Macromolecules 2013, 46, 736–746.
  163. Xiao, P.; Zhang, J.; Dumur, F.; Tehfe, M.-A.; Morlet-Savary, F.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Visible light sensitive photoinitiating systems: Recent progress in cationic and radical photopolymerization reactions under soft conditions. Prog. Polym. Sci. 2015, 41, 32–66.
  164. Kabatc, J.; Iwinska, K.; Balcerak, A.; Kwiatkowska, D.; Skotnicka, A.; Czechband, Z.; Bartkowiak, M. Onium salts improve the kinetics of photopolymerization of acrylate activated with visible light. RSC Adv. 2020, 10, 24817–24829.
  165. Crivello, J.V. The Discovery and Development of Onium Salt Cationic Photoinitiators. J. Polym. Sci. A Polym. Chem. 1999, 37, 4241–4254.
  166. Crivello, J.V.; Lam, J.H.W. Diaryliodonium Salts. A New Class of Photoinitiators for Cationic Polymerization. Macromolecules 1977, 10, 1307–1315.
  167. Topa, M.; Ortyl, J. Moving Towards a Finer Way of Light-Cured Resin-Based Restorative Dental Materials: Recent Advances in Photoinitiating Systems Based on Iodonium Salts. Materials 2020, 13, 4093.
  168. Lalevée, J.; Telitel, S.; Xiao, P.; Lepeltier, M.; Dumur, F.; Morlet-Savary, F.; Gigmes, D.; Fouassier, J.-P. Metal and metal free photocatalysts: Mechanistic approach and application as photoinitiators of photopolymerization. Beilstein J. Org. Chem. 2014, 10, 863–876.
  169. Fouassier, J.-P.; Lalevée, J. Photochemical Production of Interpenetrating Polymer Networks; Simultaneous Initiation of Radical and Cationic Polymerization Reactions. Polymers 2014, 6, 2588–2610.
  170. Tomal, W.; Chachaj-Brekiesz, A.; Popielarz, R.; Ortyl, J. Multifunctional biphenyl derivatives as photosensitisers in various types of photopolymerization processes, including IPN formation, 3D printing of photocurable multiwalled carbon nanotubes (MWCNTs) fluorescent composites. RSC Adv. 2020, 10, 32162–32182.
  171. Lalevée, J.; Morlet-Savary, F.; Dietlin, C.; Graff, B.; Fouassier, J.-P. Photochemistry and Radical Chemistry under Low Intensity Visible Light Sources: Application to Photopolymerization Reactions. Molecules 2014, 19, 15026–15041.
  172. Andrzejewska, E.; Grajek, K. Recent advances in photo-induced free-radical polymerization. MOJ Poly. Sci. 2017, 1, 58–60.
  173. Corrigan, N.; Shanmugam, S.; Xu, J.; Boyer, C. Photocatalysis in organic and polymer synthesis. Chem. Soc. Rev. 2016, 45, 6165–6212.
  174. Lalevée, J.; Tehfe, M.-A.; Morlet-Savary, F.; Graff, B.; Dumur, F.; Gigmes, D.; Blanchard, N.; Fouassier, J.-P. Photoredox catalysis for polymerization reactions. Chimia 2012, 66, 439–441.
  175. Bonardi, A.-H.; Dumur, F.; Noirbent, G.; Lalevée, J.; Gigmes, D. Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region. Beilstein J. Org. Chem. 2018, 14, 3025–3046.
  176. Banoth, R.K.; Thatikonda, A. A review on natural chalcones an update. Int. J. Pharm. Sci. Res. 2020, 11, 546–555.
  177. Morita, Y.; Takagi, K.; Fukuchi-Mizutani, M.; Ishiguro, K.; Tanaka, Y.; Nitasaka, E.; Nakayama, M.; Saito, N.; Kagami, T.; Hoshino, A.; et al. A chalcone isomerase-like protein enhances flavonoid production and flower pigmentation. Plant J. 2014, 78, 294–304.
  178. Davies, K.M.; Bloor, S.J.; Spiller, G.B.; Deroles, S.C. Production of yellow colour in flowers: Redirection of flavonoid biosynthesis in Petunia. Plant J. 1998, 13, 259–266.
  179. Rammohan, A.; Reddy, J.S.; Sravya, G.; Rao, C.N.; Zyryanov, G.V. Chalcone synthesis, properties and medicinal applications: A review. Environ. Chem. Lett. 2020, 18, 433–458.
  180. Phan, T.P.; Teo, K.Y.; Liu, Z.-Q.; Tsai, J.-K.; Tay, M.G. Application of unsymmetrical bis-chalcone compounds in dye sensitized solar cell. Chem. Data Coll. 2019, 22, 100256.
  181. Rajakumar, P.; Thirunarayanan, A.; Raja, S.; Ganesan, S.; Maruthamuthu, P. Photophysical properties and dye-sensitized solar cell studies on thiadiazole–triazole–chalcone dendrimers. Tetrahedron Lett. 2012, 53, 1139–1143.
  182. Sharma, S.; Sharma, A.S.; Agarwal, N.K.; Shahband, P.A.; Shrivastav, P.S. Self-assembled blue-light emitting materials for their liquid crystalline and OLED applications: From a simple molecular design to supramolecular materials. Mol. Syst. Des. Eng. 2020, 5, 1691–1705.
  183. Zhang, Y.-P.; Wang, B.-X.; Yang, Y.-S.; Liang, C.; Yang, C.; Chai, H.-L. Synthesis and self-assembly of chalcone-based organogels. Coll. Surf. A 2019, 577, 449–455.
  184. Chen, S.; Qin, C.; Jin, M.; Pan, H.; Wan, D. Novel chalcone derivatives with large conjugation structures as photosensitizers for versatile photopolymerization. J. Polym. Sci. 2021, 59, 578–593.
  185. Yadav, G.D.; Wagh, D.P. Claisen-Schmidt Condensation using Green Catalytic Processes: A Critical Review. ChemistrySelect 2020, 5, 9059–9085.
  186. Qian, H.; Liu, D. Synthesis of Chalcones via Claisen-Schmidt Reaction Catalyzed by SulfonicAcid-Functional Ionic Liquids. Ind. Eng. Chem. Res. 2011, 50, 1146–1149.
  187. Rafiee, E.; Rahimi, F. A green approach to the synthesis of chalcones via Claisen-Schmidt condensation reaction using cesium salts of 12-tungstophosphoric acid as a reusable nanocatalyst. Monatsh. Chem. 2013, 144, 361–367.
  188. Reza Sazegar, M.; Mahmoudian, S.; Mahmoudi, A.; Triwahyono, S.; Abdul Jalil, A.; Mukti, R.R.; Nazirah Kamarudine, N.H.; Ghoreishi, M.K. Catalyzed Claisen–Schmidt reaction by protonated aluminate mesoporous silica nanomaterial focused on the (E)-chalcone synthesis as a biologically active compound. RSC Adv. 2016, 6, 11023–11031.
  189. Narendera, T.; Venkateswarlu, K.; Vishnu Nayak, B.; Sarkar, S. A new chemical access for 30-acetyl-40-hydroxychalcones usingborontrifluoride–etherate via a regioselective Claisen-Schmidt condensation and its application in the synthesis of chalcone hybrids. Tetrahedron Lett. 2011, 52, 5794–5798.
  190. Rozmer, Z.; Perjési, P. Naturally occurring chalcones and their biological activities. Phytochem. Rev. 2016, 15, 87–120.
  191. Shivani, T.; Bhavesh, S. A review: Chemical and biological activity of chalcones with their metal complex. Asian J. Biomed. Pharmaceut. Sci. 2020, 10, 6–13.
  192. Zhuang, C.; Zhang, W.; Sheng, C.; Zhang, W.; Xing, C.; Miao, Z. Chalcone: A Privileged Structure in Medicinal Chemistry. Chem. Rev. 2017, 117, 7762–7810.
  193. Singh, P.; Anand, A.; Kumar, V. Recent developments in biological activities of chalcones: A mini review. Eur. J. Med. Chem. 2014, 85, 758–777.
  194. Jung, J.-C.; Lee, Y.; Min, D.; Jung, M.; Oh, S. Practical Synthesis of Chalcone Derivatives and Their Biological Activities. Molecules 2017, 22, 1872.
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