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Synthesis and proton-induced fluorescence “OFF–ON” switching of a new D-π-A type pyran dye

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Abstract

A new D-π-A type 4-(dicyanomethylene)-2-methyl-6-((1,4-diethyl-1,2,3,4-tetrahydroquinoxalin-6-yl)vinyl)-4H-pyran (DCM-Q) dye has been prepared by condensation. Under neutral or alkaline conditions, DCM-Q had a long absorption wavelength, because of intramolecular charge transfer (ICT), but weak fluorescence, because of photoinduced electron transfer (PET) in the excited state. In the presence of protons, the absorption wavelength of DCM-Q was blue shifted, owing to weak ICT, whereas the fluorescence intensity increased, because of limited PET. DCM-Q has potential as an efficient fluorescence “OFF–ON” switch for proton determination.

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Acknowledgments

This work was supported by the Science and Technology Commission of Shanghai Municipality (11142201100, 10520709900) and the Fundamental Research Funds for the Central Universities.

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Authors and Affiliations

  1. Key Lab for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China

    Zhidan Tian, Yunchang Liu, Baozhu Tian & Jinlong Zhang

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  1. Zhidan Tian
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  2. Yunchang Liu
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  3. Baozhu Tian
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  4. Jinlong Zhang
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Correspondence to Jinlong Zhang.

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Tian, Z., Liu, Y., Tian, B. et al. Synthesis and proton-induced fluorescence “OFF–ON” switching of a new D-π-A type pyran dye. Res Chem Intermed 41, 525–533 (2015). https://doi.org/10.1007/s11164-013-1206-0

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