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Folded and open structures of a new bis-TTF derivative, as viewed from inter- and intra-molecular interactions.pdf

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Folded and open structures of a new bis-TTF derivative, as viewed from inter- and intra-molecular interactions.pdf

Journal of Molecular Structure 737 (2005) 153–157 /locate/molstruc Folded and open structures of a new bis-TTF derivative, as viewed from inter- and intra-molecular interactions Li-Hui Caoa, Yong Zhanga, Jie Daia,b,*, Hai-Hong Lina, Wen Lua, Wen-Juan Guoa aDepartment of Chemistry and Chemical Engineering, Suzhou University, Suzhou 215006, People’s Republic of China bLaboratory of Organic Solids, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, People’s Republic of China Received 7 September 2004; revised 14 October 2004; accepted 21 October 2004 Available online 25 November 2004 Abstract A dimeric TTF derivative of bis{2-[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-4-(methylsulfanyl)-5-(methylenesulfanyl)-1,3dithiole} (1) was synthesized and characterized. The sulfur atom of a methylthio group interacts with CaC double bond of the neighboring TTF moiety exhibiting a S–p interactions within a molecular chain. The molecules are further assembled to a 2D structure by an S/S interaction (3.3441(17) A? ). Open and folded model for the molecular conformation is discussed based on the results measured in the solid state (crystal structure) and in solution (cyclic voltammogram). q 2004 Elsevier B.V. All rights reserved. Keywords: Tetrathiafulvalene; Redox properties; Molecular interaction; Crystal structure 1. Introduction Dimeric and oligomeric TTFs (TTFZtetrathiafulvalene) are currently of interest to chemists in supramolecular chemistry for their applications in organic molecular materials, redox sensors and molecular devices [1–4]. Except for bi-TTFs in which two TTFs are linked directly by s-bond [5–7], most of the reported dimeric TTFs can be divided into two types: one is linked through conjugated p-systems and the other through non-conjugated s-chains [4]. A series of bis-TTFs with alkyl chains of different lengths have been synthesized and studied [8–15]. Compared with the conjugated compounds, the non-conjugate