Synthesis and Nonlinear Optical Properties of Donor-Acceptor Substituted Triaryl Azole Derivatives

A variety of optically nonlinear chromophores containing a five-membered imidazole, oxazole, or thiazole ring have been prepared and characterized. These consist of 2,4,5-triphenyl-substituted azole heterocyclic systems in which the 2-aryl ring bears an electron-withdrawing substituent and the 4,5-aryl rings bear an electron-donating substituent. Additionally, some planar analogues, phenanthro[9,10-d]imidazoles, were also prepared and evaluated. The utility of these chromophores will be dictated by their linear absorption wavelength and oscillator strength, microscopic optical nonlinearity, ground-state dipole moment, thermal stability, and solubility. The tradeoffs between these structure-dependent properties are discussed with regard to exploitation of these chromophores as guest dyes in high-temperature thermoplastics. © 1993, American Chemical Society. All rights reserved.