Abstract
Benzo[1,2-c:3,4-c':5,6-c'']tri-thio-phene (D 3h -BTT) is an easily prepared electron donor that readily forms charge-transfer complexes with organic acceptors. We report here two crystal structures of its charge-transfer complexes with 7,7,8,8-tetra-cyano-quinodi-methane (TCNQ) and buckminsterfullerene (C60). The D 3h -BTT·TCNQ complex, C12H6S3·C12H4N4, crystallizes with mixed layers of donors and acceptors, with an estimated degree of charge transfer at 0.09 e. In the D 3h -BTT·C60·toluene complex, C12H6S3·C60·C7H8, the central ring of BTT is 'squeezed' by the C60 mol-ecules from both faces. However, the degree of charge transfer is low. The C60 unit is disordered over two sites in a 0.766 (3):0.234 (3) ratio and was refined as a two-component inversion twin.
Highlights
Conjugated sulfur-containing aromatic molecules remain the most popular choices for the preparation of organic electronic materials
Hart et al reported that D3h isomer of benzotrithiophene (D3h-BTT) formed CT complexes with several acceptor molecules including TCNQ, no structural information for any of the CT complexes was provided
We report the X-ray crystal structures of the CT complexes D3h-BTTÁTCNQ and D3h-BTTÁC60Átoluene, the latter of which exhibits the second closest pair of bilateral arene–C60 contacts
Summary
Conjugated sulfur-containing aromatic molecules remain the most popular choices for the preparation of organic electronic materials. Their planar shapes and the large 3p orbitals on sulfur atoms allow extensive intermolecular orbital overlap in the solid state. Both of these features make them very good candidates as donors in binary charge–transfer (CT) complexes (Holiday et al, 2014). The D3h isomer of benzotrithiophene (D3h-BTT) is the most highly symmetric isomer of the BTTs, and all three of its sulfur atoms point away radially from the central ring It is one of the most prepared BTT isomers (Hart et al, 1978). We report the X-ray crystal structures of the CT complexes D3h-BTTÁTCNQ and D3h-BTTÁC60Átoluene, the latter of which exhibits the second closest pair of bilateral arene–C60 contacts
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