Several new push-pull azobenzene dyes were synthesized by diazonium salt coupling of electron-poor anilines with N,N-dialkylanilines. Their dipole moments and first-order hyperpolarizabilities were evaluated respectively from the concentration dependence of the dielectric constant of solutions in apolar solvents and by the electric-field-induced-second-harmonic-generation (EFISH) technique. Investigation of the influence of both nature and steric hindrance of the electron with drawing group allowed to highlight a significant deviation from linearity in the relationship between dipole moments and first-order hyperpolarizabilities. This effect was particularly noticeable when multiple electron withdrawing groups pointing in different directions were present on the same phenyl ring.

Structure-activity relationship of new NLO organic materials based on push-pull azodyes. 1. Synthesis and molecular properties of the dyes

ALTOMARE, ANGELINA;SOLARO, ROBERTO;CIARDELLI, FRANCESCO;
1998

Abstract

Several new push-pull azobenzene dyes were synthesized by diazonium salt coupling of electron-poor anilines with N,N-dialkylanilines. Their dipole moments and first-order hyperpolarizabilities were evaluated respectively from the concentration dependence of the dielectric constant of solutions in apolar solvents and by the electric-field-induced-second-harmonic-generation (EFISH) technique. Investigation of the influence of both nature and steric hindrance of the electron with drawing group allowed to highlight a significant deviation from linearity in the relationship between dipole moments and first-order hyperpolarizabilities. This effect was particularly noticeable when multiple electron withdrawing groups pointing in different directions were present on the same phenyl ring.
N., Tirelli; Altomare, Angelina; Solaro, Roberto; Ciardelli, Francesco; U. W., Suter; U., Meier; Bosshard, C. H.; P., Günter
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/48827
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