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Pure Appl. Chem., 2012, Vol. 84, No. 4, pp. 1005-1025

Published online 2012-03-23

Tetrathiafulvalene vinylogues as versatile building blocks for new organic materials

Yuming Zhao, Guang Chen, Karimulla Mulla, Ilias Mahmud, Shuai Liang, Prateek Dongare, David W. Thompson, Louise N. Dawe and Stephen Bouzan

Department of Chemistry, Memorial University of Newfoundland, St. John’s, Newfoundland A1B 3X7, Canada

Abstract: Although tetrathiafulvalene (TTF) and its derivatives have been extensively studied as important organic electronic materials over the past half century, tetrathiafulvalene vinyl-ogues (TTFVs) still remain a relatively underdeveloped branch in the family of TTF derivatives. Our recent work has investigated the synthesis and characterization of a class of diphenyl-substituted TTFVs carrying alkynyl functionality. The unique conformational and redox properties of such TTFV derivatives along with the versatile chemistry enabled by acetylenic groups (e.g., metal-catalyzed coupling and click reactions) have led us to a variety of functional molecular architectures ranging from oligoynes, polymers, and molecular tweezers, to macrocycles. Property studies of these new TTFV-based molecular materials point to appealing applications in molecular electronics and optoelectronics.