The structure-property relationship of aryl-substituted tetrathiafulvalene vinylogues

Bouzan, Stephen (2015) The structure-property relationship of aryl-substituted tetrathiafulvalene vinylogues. Masters thesis, Memorial University of Newfoundland.

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Abstract

Tetrathiafulvalene (TTF) is well known in the discipline of materials chemistry for its excellent electron donating properties. For decades, considerable efforts have been made to design and synthesize novel -extended analogues of TTF (ex-TTFs) in order to exploit the application in electronic and optoelectronic devices. Of the vast array of ex-TTFs known so far, the class of vinylogous derivatives of TTF (TTFVs) has attracted the interest of many research groups. TTFVs are ideal candidates for organic-based electronics as they have a low band gap and rich electroactivity. This has posed the need to further investigate the interesting and inherently peculiar nature of TTFV; in particular, the structure-property relationship that exists with aryl based TTFVs has been a focus of this thesis work. Through the use of aryl substituents conformational control of TTFV has been demonstrated. The use of a 1-naphthyl substituent allowed a neutral TTFV to take an unprecedented trans conformation as a result of significant allylic strain. Additionally, an unprecedented tricyclic S-containing heterocycle was produced via ortho brominated aryl substituents. Finally, a group of alkynylated phenyl-TTFVs were synthesized and characterized. The molecular properties of all the new TTFV and related compounds have been studied by single crystal X-ray diffraction, UV-Vis absorption spectroscopy, and cyclic voltammetry.

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