Heterocyclic Azole Nonlinear Optical Chromophores. 1. Donor-Acceptor Substituted Pyrazole Derivatives

Abstract

We have described the synthesis of a variety of 1,3, 1,4, and 1,5 donor-acceptor conjugation extended substituted pyrazole derivatives and have studied their spectroscopic and nonlinear optical properties. These materials are thermally stable and absorb strongly in the UV-visible region, albeit at much shorter wavelengths than comparably substituted cyclic azapolyenes such as 2-pyrazolines. Quadratic hyperpolarizability measurements suggest that the pyrazoles are significantly nonlinear, and that 1,3 and 1,4 substitution is preferred. 1,5 substitution causes a significant drop in the nonlinearity and a blue shift in the long-wavelength absorption maximum, presumably due to a twisting and partial deconjugation of the substituents to relieve unfavorable steric interactions. The experimental results are compared with those predicted by simple “finite field” computational procedures. © 1993, American Chemical Society. All rights reserved.