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用于极大丰富各向异性力触发的高对比度三色荧光分子开关库的双(三苯胺)修饰芴发光体的分子工程

Molecular engineering of bis(triphenylamine)-modified fluorene luminophore for immensely enriching anisotropic force-triggered high-contrast tricolor fluorescent molecular switches library.

作者信息

Chen Zhao, Zou Yijie, Yin Ya, Deng Diandian, Yang Yue, Fan Congbin, Pu Shouzhi, Liu Gang

机构信息

Jiangxi Provincial Key Laboratory of Organic Functional Molecules, Institute of Organic Chemistry, Jiangxi Science and Technology Normal University Nanchang 330013 P. R. China

State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University Nanjing 210023 P. R. China.

出版信息

Chem Sci. 2025 Jun 10;16(27):12293-12302. doi: 10.1039/d5sc02314a. eCollection 2025 Jul 10.

Abstract

The preparation of anisotropic mechanical force-triggered high-contrast tricolor fluorescent solid switches is both significant and extremely challenging. Herein, we report a high-efficiency molecular engineering strategy for developing mechanochromic compounds that exhibit an infrequent yet contrasting three-color fluorescence switching feature. Notably, 14 new symmetric fluorescent molecules by introducing a variety of substituents on either side of the central organic moiety involving 4,4'-((9-fluoren-9-ylidene)methylene)bis(,-diphenylaniline) are successfully obtained, and 10 new fluorogenic compounds have been discovered to exhibit seldom-observed tricolored mechanofluorochromic phenomena. Impressively, among them, 8 luminogens demonstrate exceptionally scarce anisotropic force-triggered high-contrast three-color fluorescence responses, which is a commendable achievement, fully verifying the effectiveness of our molecular engineering strategy presented in this study. Furthermore, based on two newly developed representational mechanically responsive tricolor fluorescence switches, three advanced information anticounterfeiting systems are skillfully constructed.

摘要

制备各向异性机械力触发的高对比度三色荧光固体开关既具有重要意义,又极具挑战性。在此,我们报告了一种高效的分子工程策略,用于开发具有罕见但对比鲜明的三色荧光切换特性的机械变色化合物。值得注意的是,通过在涉及4,4'-((9-芴-9-亚基)亚甲基)双(,-二苯胺)的中心有机部分两侧引入各种取代基,成功获得了14种新的对称荧光分子,并且发现了10种新的荧光化合物表现出罕见的三色机械荧光变色现象。令人印象深刻的是,其中8种发光体表现出异常罕见的各向异性力触发的高对比度三色荧光响应,这是一项值得称赞的成就,充分验证了我们在本研究中提出的分子工程策略的有效性。此外,基于两个新开发的具有代表性的机械响应三色荧光开关,巧妙地构建了三种先进的信息防伪系统。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fa44/12242937/33d2aa301f73/d5sc02314a-f1.jpg

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