Tetrathiafulvalene-7,7,8,8-Tetracyanoquinodimethane and Tetrathiafulvalene-2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane Organic Charge-Transfer Complexes: Reusable Catalysts for Electron-Transfer Reactions

摘要

The application of organic charge-transfer complexes such as TTF-TCNQ (TTF=tetrathiafulvalene, TCNQ=7,7,8,8-tetracyanoquinodimethane) is well known in the area of organic electronics. However, the applicability of this material and its derivatives has not been explored for catalytic reactions. Herein, we report on the catalytic properties of both TTF-TCNQ and the significantly less-known fluorinated analogue TTF-TCNQF(4) (TCNQF(4)=2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane). The model reaction of ferricyanide ion reduction by thiosulfate ions was chosen, for which it was found that both materials were indeed catalytically active. Significantly, the fluorinated TCNQF(4) analogue showed considerably higher catalytic activity than TTF-TCNQ. In addition, TTF-TCNQF(4) was found to be highly stable under the catalytic conditions and could be recovered and reused without any loss in performance for at least 10 catalytic cycles. This work opens up new avenues for investigating these types of materials for catalytic reactions.