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A Comprehensive Therotical Investigation of Intramolecular Proton Transfer in the Excited States for Some Newly-designed Diphenylethylene Derivatives Bearing 2-(2-Hydroxy-Phenyl)-Benzotriazole Part

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Abstract

This article presents a comprehensive therotical investigation of excited state intramolecular proton transfer (ESIPT) for some newly-designed diphenylethylene derivatives containing 2-(2-hydroxy-phenyl)-benzotriazole moiety with various substituted groups. The calculation shows the structural parameters and Mulliken charges of phototautomers enol (E) and keto (K) of these compounds exhibit no or tiny changes from S0 to S1. The calculated results suggest that HOMO and LUMO + 1 of the compounds displays excellent overlapping nature, and thus the absorption and emission could be from the electron transition of HOMO→LUMO + 1. The electron density distribution in the frontier orbital of E and K are influenced remarkably by various substituted groups in S0 and S1 states. Electron density distribution deficiency in 2-(2-hydroxy-phenyl)-benzotriazole part is observed in L + 1 for these derivatives. The calculation also suggests the potential energy curves of ESIPT are shown to be a strong relationship with electron donor-acceptor groups. The absorption spectra, normal emission spectra and ESIPT spectra of the derivatives were also calculated.

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Acknowledgements

The authors would thank National Natural Science Foundation of China (Nos. 20776165, 20702065 and 20872184) and Natural Science Foundation of CQ CSTC (Nos. CSTC, 2010BB0216) for financial supports. The authors appreciate for the support from the Key Foundation of Chongqing Science and Technology Commission (CSTC 2008BA4020). We appreciate financial supports from the Fundamental Research Funds for the Central Universities (No.CDJZR10220006, CDJXS10221137, CDJZR10225501).

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Authors and Affiliations

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

    Hongru Li, Lanying Niu, Xiaofang Xu, Shengtao Zhang & Fang Gao

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  1. Hongru Li
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  2. Lanying Niu
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  3. Xiaofang Xu
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Correspondence to Hongru Li or Fang Gao.

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Li, H., Niu, L., Xu, X. et al. A Comprehensive Therotical Investigation of Intramolecular Proton Transfer in the Excited States for Some Newly-designed Diphenylethylene Derivatives Bearing 2-(2-Hydroxy-Phenyl)-Benzotriazole Part. J Fluoresc 21, 1721–1728 (2011). https://doi.org/10.1007/s10895-011-0867-6

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