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2,2'-二氨基-6,6'-二硼基-1,1'-联萘:一种用于温度依赖型双荧光和可切换圆偏振发光的多功能构筑块。

2,2'-Diamino-6,6'-diboryl-1,1'-binaphthyl: A Versatile Building Block for Temperature-Dependent Dual Fluorescence and Switchable Circularly Polarized Luminescence.

机构信息

School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, P. R. China.

Key Laboratory of Organic Solids, Beijing National Laboratory for Molecular Science (BNLMS), Beijing, 100190, P. R. China.

出版信息

Angew Chem Int Ed Engl. 2019 Apr 1;58(15):4840-4846. doi: 10.1002/anie.201813320. Epub 2019 Feb 15.

Abstract

Temperature-dependent dual fluorescence and switchable circularly polarized luminescence (CPL) are two highly pursued but challenging properties for small organic molecules (SOMs). We herein disclose a triarylborane π-system based on a 2,2'-diamino-6,6'-diboryl-1,1'-binaphthyl scaffold that can serve as a versatile building block for achieving these two properties by simply choosing different amino groups. BNMe -BNaph with less bulky dimethylamino groups displays temperature-dependent dual fluorescence, and can thus be used as a highly sensitive ratiometric fluorescence thermometer. On the other hand, BNPh -BNaph with bulky diphenylamino groups exhibits intense fluorescence in both solution and in the solid state. A change of solvent from nonpolar cyclohexane to highly polar MeCN not only shifts the CPL position to much longer wavelength but also inverts the CPL sign. In addition, the complexation of BNPh -BNaph with fluoride greatly enhances the CPL intensity.

摘要

温度依赖型双荧光和可切换圆偏振发光(CPL)是小分子有机化合物(SOMs)中两个备受关注但极具挑战性的性质。本文报道了一种基于 2,2'-二氨基-6,6'-二硼基-1,1'-联萘骨架的三芳基硼烷π体系,通过简单选择不同的氨基基团,它可作为实现这两种性质的多功能构建块。具有较小体积二甲氨基基团的 BNMe-BNaph 显示出温度依赖型双荧光,因此可用作高灵敏度比率荧光温度计。另一方面,具有大体积二苯胺基团的 BNPh-BNaph 在溶液和固态中均表现出强荧光。从非极性环己烷到高极性 MeCN 的溶剂变化不仅将 CPL 位置移至更长的波长,而且还反转了 CPL 符号。此外,BNPh-BNaph 与氟化物的络合极大地增强了 CPL 强度。

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