Abengozar et al. Beilstein J Org Chem. 2019;15:1257-1261. Remarkable effect of alkynyl substituents on the fluorescence properties of a BN-phenanthrene.

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Remarkable effect of alkynyl substituents on the fluorescence properties of a BN-phenanthrene.

Departamento de Quimica Organica y Quimica Inorganica, Instituto de Investigacion Quimica "Andres M. del Rio" (IQAR), Universidad de Alcala, 28871-Alcala de Henares, Madrid, Spain.

Abstract

A series of BN-phenanthrenes with substituents of a diverse nature have been synthesized by palladium-catalyzed cross-coupling reactions of a common chloro-substituted precursor, which was made from readily available materials in only four steps. Evaluation of the photophysical properties of the prepared compounds unveiled an impressive effect of the presence of alkynyl substituents on the fluorescence quantum yield, which improved from 0.01 in the parent compound to up to 0.65 in derivatives containing a triple bond.

graphical abstract