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

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 serv...

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Bibliographic Details
Published in:Angewandte Chemie 2019-04, Vol.131 (15), p.4894-4900
Main Authors: Sun, Zuo‐Bang, Liu, Jun‐Kai, Yuan, Da‐Fei, Zhao, Zheng‐Hua, Zhu, Xiao‐Zhang, Liu, Di‐Hong, Peng, Qian, Zhao, Cui‐Hua
Format: Article
Language:English
Subjects:
1,1′-Binaphthyl-Gerüste
Amino groups
Chemistry
Circular polarization
Cyclohexane
Fluorescence
Fluorides
Intramolekularer Ladungstransfer
Luminescence
Organic chemistry
Temperaturabhängige duale Fluoreszenz
Temperature dependence
Temperature effects
Triarylborane
Zirkular polarisierte Lumineszenz
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Summary: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. BNMe2‐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, BNPh2‐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 BNPh2‐BNaph with fluoride greatly enhances the CPL intensity. Die Kombination zweier Donor/π‐Akzeptor‐Einheiten in einem 2,2′‐Diamino‐6,6′‐diboryl‐1,1′‐binaphthyl‐Gerüst ergibt einen vielseitigen Baustein für organische Fluorophore mit temperaturabhängiger dualer Fluoreszenz und schaltbarer zirkular polarisierter Lumineszenz.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201813320