A new donor for charge-transfer systems: synthesis and properties of 2,4,7,9-tetramethyl-1,6-dithiapyrene (TMDTP) and structure of (TMDTP)3(PF6)2·2THF and TMDTP-TCNQ

Jesper Bendix; Klaus Bechgaard; Jørn Bolstad Christensen

doi:10.1039/d1ra00587a

A new donor for charge-transfer systems: synthesis and properties of 2,4,7,9-tetramethyl-1,6-dithiapyrene (TMDTP) and structure of (TMDTP)₃(PF₆)₂·2THF and TMDTP-TCNQ

RSC Adv. 2021 Apr 20;11(24):14607-14614. doi: 10.1039/d1ra00587a. eCollection 2021 Apr 15.

Authors

Jesper Bendix¹, Klaus Bechgaard¹, Jørn Bolstad Christensen²

Affiliations

¹ Department of Chemistry, University of Copenhagen Universitetsparken 5 DK-2100 Copenhagen Denmark.
² Department of Chemistry, University of Copenhagen Thorvaldsensvej 40 DK-1871 Frederiksberg Denmark jbc@chem.ku.dk.

Abstract

The heterocyclic donor molecule 2,4,7,9-tetramethyl-1,6-dithiapyrene (TMDTP) has been synthesized in five steps. Oxidation of TMDTP is facile (E ₁ ^1/2 = 0.27 V and E ₂ ^1/2 = 0.79 V vs. SCE). The charge-transfer complex, TMDTP-TCNQ, has been prepared and the salt, (TMDTP)₃(PF₆)₂·2THF, obtained by electrocrystallization. The structure of TMDTP, TMDTP-TCNQ and (TMDTP)₃(PF₆)₂·2THF has been characterized by X-ray crystallography and computationally.