光致变色
汞菁
阳离子聚合
光化学
部分
荧光
化学
吸收(声学)
量子产额
共轭体系
材料科学
立体化学
高分子化学
有机化学
聚合物
光学
物理
复合材料
作者
Anastasia S. Kozlenko,Ilya V. Ozhogin,A. D. Pugachev,Ирина А. Ростовцева,Н. И. Макарова,Natalya V. Demidova,В. В. Ткачев,Г. С. Бородкин,Anatoly V. Metelitsa,Islam M. El-Sewify,B. S. Lukyanov
标识
DOI:10.1016/j.saa.2023.122712
摘要
Visible-light-mediated photochromic compounds with NIR absorption and fluorescence are of great interest for use in different biomedical applications. In this work, new representatives of spiropyrans with conjugated cationic 3H-indolium substituents in different positions of 2H-chromene moiety were synthesized. The electron-donating methoxy groups were introduced in the uncharged indoline and charged indolium cycles to form the effective conjugation chain between the hetarene moiety and the cationic fragment for reaching NIR absorption and fluorescence. The molecular structure and the effects of cationic fragment position on the mutual stability of the spirocyclic and merocyanine forms of compounds were carefully studied in the solutions and solid state by NMR, IR, HRMS, single-crystal XRD, and quantum chemical calculations. It was found that the obtained spiropyrans demonstrate positive or negative photochromism depending on the cationic fragment's position. One of spiropyrans has shown bidirectional photochromic properties induced exclusively by visible light of different wavelengths in both directions. The photoinduced merocyanine forms of compounds possessed far-red shifted absorption maxima and NIR fluorescence, which makes them prospective fluorescent probes for bioimaging.
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