Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 35, Pages 6117-6121Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201901151
Keywords
Azides; Fluorescence; Fluoride ion sensing; Triarylboranes; Triazoles
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Funding
- Japan Science Society
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Tris(4-azido-2,6-dimethylphenyl)borane was readily synthesized from an amino-substituted triarylborane using tert-butyl nitrite and trimethylsilylazide. This compound can easily be converted into triarylboranes bearing various pi-conjugated moieties with triazole ring pi-linkers through a Huisgen cycloaddition. UV/Vis absorption spectra and DFT calculations suggested that constructing a triazole linker successfully extended the pi-conjugated system of triarylboranes. Triarylboranes obtained using this method maintained their fluorescent nature. In particular, the triarylborane linking N,N-dimethylaminophenyl groups with triazole rings exhibited notable visible solvatofluorochromism and fluorescence color change upon addition of a fluoride anion.
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