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

doi:10.1016/j.cjche.2024.04.016

Abstract

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

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

Xiaoming Zhu, Yunting Liu, Mingyue Cao, Guangle Niu. Simple substituents make big differences in photophysical performances of 2,1,3-benzothiadizole-conjugated spiropyrans[J]. Chinese Journal of Chemical Engineering, 2024, 72(8): 53-59.

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