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Synthesis, Spectroscopy and Photochemistry of Novel Branched Fluorescent Nitro-Stilbene Derivatives with Benzopheonone Groups

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Abstract

In this article, we presented novel nitro-stilbene derivatives with one or two benzophenone groups as photoinitiators via multi-steps synthesis. The ultraviolet/visible spectroscopy and the emission spectroscopy of the compounds were determined in various solvents. The results showed that the ultraviolet/visible absorption spectroscopy of the derivatives with benzophenone moiety displayed overlap effects of nitro-stilbene and benzophenone parts. In non-polar solvents, the derivatives exhibited strong emission, while they displayed weak emission in modest and strong polar solvents. Dyes-linked benzopheonone groups displayed stronger fluorescence emission than simple chromophore parent molecules. Visible-light photoinitiating effects of the derivatives were investigated extensively. Methyl methacrylate could be photoinitiated efficiently by the derivatives with benzophenone moieties at very low concentration, even at 1 × 10−5 mol/L. While the photopolymerization efficiency of styrene initiated by the derivatives was lower than that of methyl methacrylate. Our results showed that the dye-linked photoinitators had more efficient photoinitiating than the simple mixture of dye and photoinitator. Furthermore, the derivative with two benzophenone groups displayed more excellent phototiniatiating effects than the derivative with one benzophenone group. Thermodynamics driving for the occurrence of visible-light photoinduced intramolecular electron transfer from chromophore part to benzophenone part was evaluated. Benzopinacol moiety produced in photoreaction was confirmed by nuclear magnetic resonant spectroscopy. Thermal stability of the derivatives was analyzed.

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Acknowledgements

The authors appreciate financial support from National Natural Science Foundation of China (Nos. 20776165, 20702065, 20872184). We would thank the “Foundation of Chongqing Science and Technology Commission” (CSTC2008BA4020, CSTC2009BB4216). H. Li thanks “A Foundation for the Author of National Excellent Doctoral Dissertation of PR China (200735)” for financial support. This paper is partly sponsored by the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry as well (Nos. 20071108-1, 20071108-5). The support from Innovative Talent Training Project, the Third State of “211 Project”, Chongqing University (S-09103) is greatly appreciated.

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  1. College of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 400044, China

    Fang Gao, Jian Liu, Huayong Peng, Nvdan Hu, Hongru Li & Shengtao Zhang

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  1. Fang Gao
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  2. Jian Liu
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Correspondence to Fang Gao.

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Gao, F., Liu, J., Peng, H. et al. Synthesis, Spectroscopy and Photochemistry of Novel Branched Fluorescent Nitro-Stilbene Derivatives with Benzopheonone Groups. J Fluoresc 20, 703–712 (2010). https://doi.org/10.1007/s10895-010-0611-7

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