Synthesis and absorption/emission spectroscopic properties of bis(phenylethynyl)benzenes and 9,10-bis(phenylethynyl)anthracenes

Abstract

A series of bis(phenylethynyl)benzenes 3 and 9,10-bis(phenylethynyl)anthracenes 4 was synthesized by bromination–dehydrobromination reaction or newly developed direct CC triple bond formation reaction from styrylstilbenes 1 or distyrylanthracenes 2. Subsequently systematic investigations were carried out on their absorption and fluorescence spectra, and their chemiluminescence properties. The following points are apparent; (a) a linear relationship between ν with combining macron]"> and Hammett's σ_p of compounds 3 and 4 was observed, (b) a significant relationship between the Stokes' shift of 4 and σ_p was observed and (c) in the series of compounds 4 the electron-donating ability of the substituents has a pronounced effect on the chemiluminescence properties.