Simple substituents make big differences in photophysical performances of 2,1,3-benzothiadizole-conjugated spiropyrans
作者机构：Shandong Univ State Key Lab Crystal Mat Jinan 250100 Peoples R China Beijing Inst Technol Sch Chem & Chem Engn Beijing 100081 Peoples R China
出 版 物：《CHINESE JOURNAL OF CHEMICAL ENGINEERING》 (中国化学工程学报（英文版）)
年 卷 期：2024年第72卷第8期
页 面：53-59页
核心收录：
学科分类：081704[工学-应用化学] 07[理学] 0817[工学-化学工程与技术] 08[工学] 070303[理学-有机化学] 0703[理学-化学]
基 金：National Natural Science Foundation of China Natural Science Foundation of Shandong Province, China [2022HWYQ-0 07, ZR2021QB043] Special Fund of Taishan Scholars Project of Shandong Province, China [tsqn201909012]
主 题：Spiropyran 2,1,3-Benzothiadiazole Photochromism Fluorescent dye Fluorescence imaging AGGREGATION-INDUCED EMISSION PROBES SWITCH CELLS
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-NO 2 and BTSP-NMe 2 ) 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-acceptorsubstituted BT-SP-NO 2 exhibited excellent photochromic behavior under multiple alternating UV-Vis irradiation, while the electron-donor-substituted BT-SP-NMe 2 was an acidochromic dye. In addition, the substituent groups distinctly affected the packing modes of these spiropyrans in the solid state. BTSP-NMe 2 showed a much stronger solid-state emission (QY of 59.0%) than BT-SP-NO 2 . Moreover, these two dyes were utilized as biocompatible probes for the speci fic light-up imaging of lipid droplets. (c) 2024 The Chemical Industry and Engineering Society of China, and Chemical Industry Press Co., Ltd. All rights are reserved, including those for text and data mining, AI training, and similar technologies.
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