Crystal structures of two charge-transfer com-plexes of benzo[1,2- c:3,4- c':5,6- c'']tri-thio-phene (D 3 h -BTT)

Qian Qin; Joel T Mague; Haley E Gould; Samuel E Vasquez; Anthony E Heyer

doi:10.1107/S2056989019013161

Crystal structures of two charge-transfer com-plexes of benzo[1,2- c:3,4- c':5,6- c'']tri-thio-phene (D _{3 h} -BTT)

Acta Crystallogr E Crystallogr Commun. 2019 Sep 30;75(Pt 10):1573-1577. doi: 10.1107/S2056989019013161. eCollection 2019 Oct 1.

Authors

Qian Qin¹, Joel T Mague², Haley E Gould¹, Samuel E Vasquez¹, Anthony E Heyer¹

Affiliations

¹ Department of Chemistry and Biochemistry, Loyola University, New Orleans, LA, 70118, USA.
² Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.

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.

Keywords: C60; TCNQ; benzotrithiophene; charge–transfer complex; crystal structure.

Grants and funding

This work was funded by National Science Foundation, MRI grant 1228232. Tulane University grant . Loyola University New Orleans grant .