Boranil dyes bearing tetraphenylethene: Synthesis, AIE/AIEE effect properties, pH sensitive properties and application in live cell imaging

被引：21

作者：

Chen, Shengxin ^{[1
]}

Qiu, Rongmao ^{[1
]}

Yu, Qiuhan ^{[1
]}

Zhang, Xueyan ^{[1
]}

Wei, Ming ^{[2
]}

Dai, Zhenya ^{[1
]}

机构：

[1] China Pharmaceut Univ, Sch Pharm, Dept Med Chem, Jiangsu Key Lab Drug Design & Optimizat, 24 Tongjiaxiang, Nanjing, Jiangsu, Peoples R China

[2] Jiangsu Prov & Chinese Acad Sci, Inst Bot, Nanjing, Jiangsu, Peoples R China

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 27期

基金：

中国国家自然科学基金;

关键词：

Boranils; pH sensitivity; Tetraphenylethene; X-ray diffraction; Cell imaging; AGGREGATION-INDUCED EMISSION; N-B INTERACTION; PHOTOPHYSICAL PROPERTIES; FACILE SYNTHESIS; BORON-COMPLEXES; MECHANOCHROMIC LUMINESCENCE; FLUORESCENT-PROBE; ENERGY-TRANSFER; BRIDGED DIMERS; BETA-DIKETONES;

D O I：

10.1016/j.tetlet.2018.05.081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A serial of novel fluorescent boranil dyes (7, 8, 9, 10) bearing tetraphenylethene were prepared through an efficient process. These dyes exhibited large stokes shifts (more than 5000 cm(-1)) and moderate fluorescent quantum yield from 0.22-0.53. Dye 9 exhibited AIE/AIEE and exhibited weak fluorescence in pure MeCN or the MeCN/water mixture with a water fraction below 80%, in which a significant AIEE effect was observed in the mixture with 80% of water fraction and a sharp increasement in fluorescence intensity was also observed. And dye 8 and 10 showed moderate solvatochromism with the solvent changed from toluene to DMSO, and they displayed sensitivities to pH change in MeCN/water solution. Interestingly, dyes 8 and 10 obtained by column chromatography and slow solvent evaporation showed different Xray diffraction properties. Moreover, compound 8 and 10 could be applied to cell imaging. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：2671 / 2678

页数：8

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