D–D–A dyes with phenothiazine–carbazole/triphenylamine as double donors in photopolymerization under 455 nm and 532 nm laser beams

作者: T. F. Zhou , X. Y. Ma , W. X. Han , X. P. Guo , R. Q. Gu

DOI: 10.1039/C6PY00918B

关键词: PolymerizationVisible spectrumMaterials scienceElectron acceptorRadical polymerizationPhotopolymerPolymer chemistryCarbazoleCationic polymerizationTriphenylaminePhotochemistry

摘要: In order to enhance electron-donating ability and absorptivity in the visible region of spectrum, four novel organic dyes (CPC, TPC, CPN TPN) with carbazole–phenothiazine or triphenylamine–phenothiazine as double electron donors (D), cyanoacrylic acid an aldehyde group acceptor (A) have been designed synthesized. The exhibit charge transfer properties ground excited states absorb strongly spectral range 380–550 nm. Upon exposure irradiation a laser diode at 455 532 nm, together iodonium salt induced high polymerization efficiency cationic bisphenol-A epoxy resin A (DGEBA) free radical tripropylene glycol diacrylate (TPGDA). An electron-transfer photosensitization mechanism was established based on steady-state photolysis experiments, theoretical calculations molecular orbitals, electrochemical analysis. Our results showed that these would extensive application photopolymerization promoted by soft light.

参考文章(67)
Knut Rurack, Fluorescence Quantum Yields: Methods of Determination and Standards Springer, Berlin, Heidelberg. pp. 101- 145 ,(2008) , 10.1007/4243_2008_019
Jing Zhang, Damien Campolo, Frederic Dumur, Pu Xiao, Didier Gigmes, Jean Pierre Fouassier, Jacques Lalevée, The carbazole-bound ferrocenium salt as a specific cationic photoinitiator upon near-UV and visible LEDs (365–405 nm) Polymer Bulletin. ,vol. 73, pp. 493- 507 ,(2016) , 10.1007/S00289-015-1506-1
Pu Xiao, Jacques Lalevée, Jiacheng Zhao, Martina H Stenzel, None, N-Vinylcarbazole as Versatile Photoinaddimer of Photopolymerization under Household UV LED Bulb (392 nm) Macromolecular Rapid Communications. ,vol. 36, pp. 1675- 1680 ,(2015) , 10.1002/MARC.201500214
Merve Kara, Sajjad Dadashi-Silab, Yusuf Yagci, Phenacyl Ethyl Carbazolium as a Long Wavelength Photoinitiator for Free Radical Polymerization. Macromolecular Rapid Communications. ,vol. 36, pp. 2070- 2075 ,(2015) , 10.1002/MARC.201500446
Fatmanur Kasapoglu, Yusuf Yagci, Photosensitized Cationic Polymerization of Cyclohexene Oxide Using a Phenacylanilinium Salt Macromolecular Rapid Communications. ,vol. 23, pp. 567- 570 ,(2002) , 10.1002/1521-3927(20020601)23:9<567::AID-MARC567>3.0.CO;2-8
Han Young Woo, Bin Liu, Bernhard Kohler, Dmitry Korystov, Alexander Mikhailovsky, Guillermo C. Bazan, Solvent Effects on the Two-Photon Absorption of Distyrylbenzene Chromophores Journal of the American Chemical Society. ,vol. 127, pp. 14721- 14729 ,(2005) , 10.1021/JA052906G
K. R. Justin Thomas, Ying-Chan Hsu, Jiann T. Lin, Kun-Mu Lee, Kuo-Chuan Ho, Chin-Hung Lai, Yi-Ming Cheng, Pi-Tai Chou, 2,3-Disubstituted Thiophene-Based Organic Dyes for Solar Cells Chemistry of Materials. ,vol. 20, pp. 1830- 1840 ,(2008) , 10.1021/CM702631R
Yiting Hao, Han Shih, Zachary Muňoz, Arika Kemp, Chien-Chi Lin, Visible light cured thiol-vinyl hydrogels with tunable degradation for 3D cell culture. Acta Biomaterialia. ,vol. 10, pp. 104- 114 ,(2014) , 10.1016/J.ACTBIO.2013.08.044
J.V. Crivello, J. Ma, F. Jiang, H. Hua, J. Ahn, R. Acosta Ortiz, Advances in the design of photoinitiators, photo-sensitizers and monomers for photoinitiated cationic polymerization Macromolecular Symposia. ,vol. 215, pp. 165- 178 ,(2004) , 10.1002/MASY.200451114