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Investigation of Triangle Terthiophene and Hydroxyphenylbenzothiazole Configured Fluorescent Dye with a Triple Bond Bridge

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Abstract

A photochromic dye was constructed by incorporation of a carbon–carbon triple bond spaced triangle terthiophene skeleton and hydroxyphenylbenzothiazole. Regular photochromic behavior was investigated with alternated UV (254 nm) and visible light (≥ 400 nm) irradiation. The color of dye in solution can be cycled between pink and colorless. Additionally, the dye solution strongly fluoresces in THF with the absolute quantum yield (QY) being 0.56. When irradiation with 254 nm light, the emissive solution can be effectively quenched to photo-stationary sate (Φ = 0.05). An emission “on–off” cycle could be established based on the UV/visible light irradiation cycle. The photochromic dye also exhibits good photo- and thermal-stability at room temperature. The emission decay profile indicates typical single component character with the fluorescence lifetime being 6.68 ns. The emission color was determined by the CIE 1931 coordinates of x = 0.14, y = 0.25 in the blue region.

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Scheme 1
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Funding

This work was supported by the National Natural Science Foundation of China (grant no. 21772034) We also thank the financial support from Henan Key Laboratory of Organic Functional Molecules and Drug Innovation.

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Authors and Affiliations

  1. School of Medicine, Huanghe Science and Technology University, Zhengzhou, Henan, People’s Republic of China

    Guangqian Ji & Qiaozhi Hou

  2. Henan Key Laboratory of Medical Polymer Materials Technology and Application, Tuoren Medical Device Research & Development Institute Co., Ldt., Xinxiang, Henan, People’s Republic of China

    Guangqian Ji

  3. NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, People’s Republic of China

    Junna Zhang & Xiaochuan Li

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Contributions

All authors contributed to the study conception and design. Material preparation, data collection and analysis were performed by Guangqian Ji, Qiaozhi Hou and Junna Zhang. The first draft of the manuscript was written by Guangqian Ji and Xiaochuan Li. Junna Zhang prepared Figs. 1, 2, 3, 4 and 5 and Qiaozhi Hou prepared Schemes 1 and 2. All authors read and approved the final manuscript.

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Correspondence to Xiaochuan Li.

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Ji, G., Hou, Q., Zhang, J. et al. Investigation of Triangle Terthiophene and Hydroxyphenylbenzothiazole Configured Fluorescent Dye with a Triple Bond Bridge. J Fluoresc 33, 153–159 (2023). https://doi.org/10.1007/s10895-022-03049-3

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