SCI和EI收录∣中国化工学会会刊

中国化学工程学报 ›› 2024, Vol. 72 ›› Issue (8): 53-59.DOI: 10.1016/j.cjche.2024.04.016

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Simple substituents make big differences in photophysical performances of 2,1,3-benzothiadizole-conjugated spiropyrans

Xiaoming Zhu1, Yunting Liu1, Mingyue Cao1, Guangle Niu2   

  1. 1 State Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, China;
    2 School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, China
  • 收稿日期:2024-02-08 修回日期:2024-04-17 出版日期:2024-08-28 发布日期:2024-10-17
  • 通讯作者: Guangle Niu,E-mail:niugl@bit.edu.cn
  • 基金资助:
    This work was supported by the National Natural Science Foundation of China (62105184); the Natural Science Foundation of Shandong Province, China (2022HWYQ-007 and ZR2021QB043); and the Special Fund of Taishan Scholars Project of Shandong Province, China (tsqn201909012).

Simple substituents make big differences in photophysical performances of 2,1,3-benzothiadizole-conjugated spiropyrans

Xiaoming Zhu1, Yunting Liu1, Mingyue Cao1, Guangle Niu2   

  1. 1 State Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, China;
    2 School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, China
  • Received:2024-02-08 Revised:2024-04-17 Online:2024-08-28 Published:2024-10-17
  • Contact: Guangle Niu,E-mail:niugl@bit.edu.cn
  • Supported by:
    This work was supported by the National Natural Science Foundation of China (62105184); the Natural Science Foundation of Shandong Province, China (2022HWYQ-007 and ZR2021QB043); and the Special Fund of Taishan Scholars Project of Shandong Province, China (tsqn201909012).

摘要: Developing multifunctional spiropyran dyes is of particular importance in diverse applications. In the present study, we synthesized two 2,1,3-benzothiadiazole-conjugated spiropyrans (BT-SP-NO2 and BT-SP-NMe2) with distinct substituents. These donor-acceptor-structured spiropyrans exhibited typical twisted intramolecular charge transfer features and strong emissions in low-polarity solvents with fluorescence quantum yields (QYs) of up to 90.7%. Like traditional spiropyrans, the electron-acceptor-substituted BT-SP-NO2 exhibited excellent photochromic behavior under multiple alternating UV-Vis irradiation, while the electron-donor-substituted BT-SP-NMe2 was an acidochromic dye. In addition, the substituent groups distinctly affected the packing modes of these spiropyrans in the solid state. BT-SP-NMe2 showed a much stronger solid-state emission (QY of 59.0%) than BT-SP-NO2. Moreover, these two dyes were utilized as biocompatible probes for the specific light-up imaging of lipid droplets.

关键词: Spiropyran, 2,1,3-Benzothiadiazole, Photochromism, Fluorescent dye, Fluorescence imaging

Abstract: Developing multifunctional spiropyran dyes is of particular importance in diverse applications. In the present study, we synthesized two 2,1,3-benzothiadiazole-conjugated spiropyrans (BT-SP-NO2 and BT-SP-NMe2) with distinct substituents. These donor-acceptor-structured spiropyrans exhibited typical twisted intramolecular charge transfer features and strong emissions in low-polarity solvents with fluorescence quantum yields (QYs) of up to 90.7%. Like traditional spiropyrans, the electron-acceptor-substituted BT-SP-NO2 exhibited excellent photochromic behavior under multiple alternating UV-Vis irradiation, while the electron-donor-substituted BT-SP-NMe2 was an acidochromic dye. In addition, the substituent groups distinctly affected the packing modes of these spiropyrans in the solid state. BT-SP-NMe2 showed a much stronger solid-state emission (QY of 59.0%) than BT-SP-NO2. Moreover, these two dyes were utilized as biocompatible probes for the specific light-up imaging of lipid droplets.

Key words: Spiropyran, 2,1,3-Benzothiadiazole, Photochromism, Fluorescent dye, Fluorescence imaging