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Paper | Regular issue | Vol 63, No. 7, 2004, pp.1577-1584
Published online, 27th April, 2004
DOI: 10.3987/COM-04-10083
Synthesis and Electrochemical Properties of π-Extended N-Arylpyrrolo[3,4-d]tetrathiafuluvalenes

Bingzhu Yin,* Yonghua Yang, Zhiqi Cong, and Kimiaki Imafuku*

*Department of Chemistry, Faculty of Science, Kumamoto University, Kurokami 2-39-1, Kumamoto 860-8555, Japan


A series of π-extended N-arylpyrrolo[3,4-d]tetrathiafulvalenes, N-aryl-2-[4,5-bis(ethylthio)-1,3-dithiole-2-ylidene]-(1,3)-dithiolo[4,5-c]pyrroles, (3a-d) were prepared via cross-coupling of 4,5-bis(ethylthio)-1,3-dithiol-2-one (12) with N-aryl-(1,3)-dithiolo[4,5-c]pyrrole-2-thiones (11a-d). The latters were obtained by the reactions of 4,5-bis(bromomethyl)-1,3-dithiole-2-thione (8) with aromatic amines (9a-d). Electrochemical behavior of compounds (3a-d) was studied by means of cyclic voltammetry. It was found that all these compounds (3a-d) have comparable to or lower half-wave potentials than those of N-alkyl-pyrrolo[3,4-d]tetrathiafulvalenes (2a-c).