Synthesis and properties of quinone derivatives

Abstract

Part I. Synthesis and properties of naphthoquinone-derived 2-amino-1,2,3-triazoles. A unique 2-amino-1,2,3-triazole system was formed by the reaction of a azide and a organophosphine. This reaction system was not reported before. The reaction properties of this system were investigated. 6 new compounds were synthesized. Among them, 34 structures were ascertained by X-ray analysis. The interesting structures, intense photoluminescence and strong UV absorption show the broad potential application of this series of compounds. Part II. Synthesis and properties of quinone-dithiols as precursors of organic conductors. Based on the previous work in our group, aimed at the exploration of new organic conductors and even superconductors, the research focused on the study of synthesis and properties of quinone dithiols in two directions: (1) Naphthoquinone dithioethers and dithiolene metal complexes (2) Benzoquinone-dithiole derivatives. In the first part, naphthoquinone thioethers and dithioethers of phenyl, benzyl and p-methoxyl-benzyl and metal naphthoquinone dithiolene complexes, $\rm\lbrack Ni(nqdt)\sb2\rbrack\sp{2-}\lbrack$(n-butyl)$ \rm\sb4N\sp{+}\rbrack\sb{2+},\ \lbrack Ni(nqdt)\sb2\rbrack\sp{1-}$(n-butyl)$\rm\sb4N\sp{+}$ and $\rm\lbrack Pd(nqdt)\sb2\rbrack\sp{2-}\lbrack$(n-butyl)$\rm\sb4N\sp{+}\rbrack \sb2,$ were synthesized and 9 structures of them were studied by X-ray diffraction. A unique 2-amino-1,2,3-triazole system was discovered unexpectedly during the research. In the second part, the synthesis of benzoquinone-derived 1,3-dithiole-2-ones and-thiones were explored. Along the synthetic pathway, 12 compounds were obtained and 10 structures of them were confirmed by X-ray analysis for the first time. All of the compounds above were characterized by chemical analysis, IR, NMR and MS.