Issue 5, 2011

A binaphthol-substituted tetrathiafulvalene with axial chirality and its enantiopure TCNQF4 charge-transfer salts

Abstract

A chiral tetrathiafulvalene (1) bearing a binaphtholdimethylene moiety on one side, an ethylenedithio substituent on the other side, is prepared from atropoisomeric (R)-, (S)- and racemic (R,S)-binaphthol. Its oxidation potential (0.49 V vs.SCE) allows for its oxidation with TCNQF4. Crystal structures of the neutral racemic (R,S)-1 and enantiopure (R)-1 were determined together with those of the enantiopure charge-transfer salts formulated as [(R)-1][TCNQF4]·CH2Cl2 and [(S)-1][TCNQF4]·CH2Cl2, the first enantiomeric salts of chiral TTFs with axial chirality. Despite the peculiar geometry adopted by the binaphthyl moieties in the constrained ten-membered ring in 1, stacking of the donor molecules is observed, both in the neutral state and in the TCNQF4 charge transfer salts where the (1)+˙ and (TCNQF4)˙ radical species are associated, respectively, into [(1)2]2+ and [(TCNQF4)2]2 homodyads, both in their singlet state.

Graphical abstract: A binaphthol-substituted tetrathiafulvalene with axial chirality and its enantiopure TCNQF4 charge-transfer salts

Supplementary files

Article information

Article type
Paper
Submitted
18 Jan 2011
Accepted
15 Feb 2011
First published
10 Mar 2011

New J. Chem., 2011,35, 1004-1010

A binaphthol-substituted tetrathiafulvalene with axial chirality and its enantiopure TCNQF4 charge-transfer salts

A. Saad, O. Jeannin and M. Fourmigué, New J. Chem., 2011, 35, 1004 DOI: 10.1039/C1NJ20034H

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