Synthesis and Photophysical Properties of Two Intramolecular Charge-transfer Chromophores obtained by [2+2] Cycloaddition of TCNE and TCNQ to an Electron-rich Alkyne

摘要

A disubstituted alkyne containing triphenylamine and phenyl groups as key compound, was prepared by Sonogashira cross-coupling reaction between phenylacetylene and (4-iodophenyl)diphenylamine. Cycloaddition of two strong electron acceptors, i.e., tetracyanoethylene (TCNE) and 7,7,8,8-tetra-cyanoquinodimethane (TCNQ) to this electron-rich alkyne led to compounds (TPA-CN and TPA-CNQ) containing both donor and acceptor groups. All compounds were characterized by 'H-NMR and FTIR spectroscopy, while the photophysical and electroctrochemical properties were investigated by UV-Vis, fluorescence spectroscopy and cyclic ooltammetry.