Synthesis and characterization of molecular materials with potential optical and electronic applications

Abstract

Chapter I. Synthesis and characterization of 2-amino-1,2,3-triazole-quinone derivatives with potential non-linear optical properties . Based on previous synthetic work in our group, twenty new quinonetriazole derivatives were prepared. The hyperpolarizabilities (? CT ) of twelve compounds were measured by the solvatochromic method. Three of the compounds show large ? CT values comparable to the best organometallic NLO materials reported. All compounds were characterized by elemental analysis, IR, UV-Visible spectroscopy, 1 H-NMR, MS and cyclic voltammetry. Fifteen crystal structures were determined by X-ray diffraction analysis. Chapter II. N-phenyl maleimide derivatives with strong visible light emission . During our work on the synthesis of 2-amino-1,2,3-triazole derivatives, several new N-phenyl-maleimide derivatives were synthesized by the Staudinger reaction of the 2,3-diazido-N-aryl-maleimides with triarylphosphines and by reaction of 2,3-dichloro-N-aryl-maleimide with thiophenol or benzylmercaptan to yield thiolates. Some of these compounds exhibit strong yellow and red emission when irradiated with UV-light. Each compound was characterized by 1 H-NMR, IR, cyclic voltammetry, UV-Visible spectroscopy and X-ray structural analysis. Four crystal structures were determined by X-ray diffraction. Chapter III. 1,3-dithiole-4,5-dithiolo-2-thione and 1,3-dithiole-2-thione quinone derivatives with potential non-linear optical and electrical conductivity properties . The reaction of the readily available [Zn(dmit) 2 ](TBA) 2 salt (dmit = 1,3-dithiol-2-thione-4,5-dithiolate) with vicinal dihalogenated quinones yielded new sulfur containing dithiin quinones. S¿¿S and S¿¿O intermolecular interactions less than the van der Waals radii were found. The compounds behave as electron acceptors and may be used as part of charge transfer complexes with potential good conductivity. The compounds were characterized by chemical analysis, MS, IR, 1 H-NMR, mass spectroscopy, UV-Visible spectroscopy and X-ray diffraction. Five crystal structures were determined by X-ray diffraction analysis.