Abstract
Six new carbazole based compounds (Ca1-Ca6) are synthesized and proposed as high performance photoinitiators with iodonium salt (iod) and/or an amine (EDB) for both the free radical polymerization (FRP) of acrylates and the cationic polymerization (CP) of epoxides upon near UV and visible light exposure using light emitting diodes (LEDs) @385 nm and @405 nm. Excellent polymerization initiating abilities are found and high final reactive function conversions are acquired. A full picture of the involved photochemical mechanisms is given.
Similar content being viewed by others
References
J.-P. Fouassier and J. Lalevée, Photoinitiators for Polymer Synthesis, Scope, Reactivity, and Efficiency, Wiley-VCH Verlag GmbH & Co.KGaA, Weinheim, 2012.
J.-P. Fouassier, Photoinitiator, Photopolymerization and Photocuring: Fundamentals and Applications, Hanser, Cincinnati, Gardner Publications, New York, 1995.
K. A. Dietliker, Compilation of Photoinitiators Commercially Available for UV Today, Sita Technology Ltd, Edinbergh, London, 2002.
S. Davidson, Exploring the Science, Technology and Application of UV and EB Curing, Sita Technology Ltd, London, 1999.
M. A. Tasdelen, G. Yilmaz, B. Iskin and Y. Yagci, Macromolecules, 2012, 45, 56–61.
J. H. Lee, R. K. Prud'Homme and I. A. Aksay, J. Mater. Res., 2001, 16, 3536–3544.
J.-P. Fouassier and J. Lalevée, Photochemistry, 2015, 42, 215–232.
F. Dumur, D. Gigmes, J.-P. Fouassier and J. Lalevée, Acc. Chem. Res., 2016, 49, 1980–1989.
C. Dietlin, S. Schweizer, P. Xiao, J. Zhang, F. Morlet-Savary, B. Graff, J.-P. Fouassier and J. Lalevée, Polym. Chem., 2015, 6, 3895–3912.
N. Zivic, M. Bouzrati-Zerelli, A. Kermagoret, F. Dumur, J.-P. Fouassier, D. Gigmes and J. Lalevée, ChemCatChem, 2016, 8, 1617–1631.
J. Lalevée, N. Blanchard, M.-A. Tehfe, M. Peter, F. Morlet-Savary, D. Gigmes and J.-P. Fouassier, Polym. Chem., 2011, 2, 1986–1991.
J. Lalevée, N. Blanchard, M.-A. Tehfe, M. Peter, F. Morlet-Savary and J.-P. Fouassier, Macromol. Rapid Commun., 2011, 32, 917–920.
D. Rehm and A. Weller, Isr. J. Chem., 1970, 8, 259–271.
J. Lalevée, N. Blanchard, M.-A. Tehfe, F. Morlet-Savary and J.-P. Fouassier, Macromolecules, 2010, 43, 10191–10195.
J. B. Foresman and A. Frisch, Exploring Chemistry with Electronic Structure Methods, Gaussian. Inc., Pittsburgh, PA, 15106 USA, 2nd edn, 1996.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, J. R.-E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W.-M. Chen, W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian 03, Revision B-2, Gaussian, Inc., Pittsburgh PA, 2003.
A. A. Mousawi, D. M. Lara, G. Noirbent, F. Dumur, J. Toufaily, T. Hamieh, T.-T. Bui, F. Goubard, B. Graff, D. Gigmes, J.-P. Fouassier and J. Lalevée, Macromolecules, 2017, 50, 4913–4926.
J. Lalevée, M.-A. Tehfe, A. Zein-Fakih, B. Ball, S. Telitel, F. Morlet-Savary, B. Graff and J.-P. Fouassier, ACS Macro Lett., 2012, 1, 802–806.
Acknowledgements
The authors thank the “Agence Nationale de la Recherche” (ANR) for the grant “FastPrinting”.
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Al Mousawi, A., Arar, A., Ibrahim-Ouali, M. et al. Carbazole-based compounds as photoinitiators for free radical and cationic polymerization upon near visible light illumination. Photochem Photobiol Sci 17, 578–585 (2018). https://doi.org/10.1039/c7pp00400a
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/c7pp00400a