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Issue 19, 2014
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Charge transfer complexes and radical cation salts of chiral methylated organosulfur donors

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Abstract

The single crystal X-ray structure of the all-axial conformer of the (R,R,R,R) enantiomer of the chiral donor tetramethyl-BEDT-TTF (TM-BEDT-TTF) was described and compared to the all-equatorial conformer. (S,S,S,S)-Tetramethyl-BEDT-TTF formed crystalline 1 : 1 complexes with TCNQ and TCNQ-F4, as well as a THF solvate of the TCNQ complex. Donors bis((2S,4S)-pentane-2,4-dithio)tetrathiafulvalene and (ethylenedithio)((2S,4S)-pentane-2,4-dithio)tetrathiafulvalene, which contain seven-membered rings bearing chirally oriented methyl groups, only formed complexes with TCNQ-F4. The TCNQ-F4 complexes contain planar organosulfur systems, in contrast to the TCNQ complexes in which there is minimal charge transfer. A variety of crystal packing modes were observed. Electrocrystallization experiments with both enantiomers and the racemic form of tetramethyl-BEDT-TTF afforded mixed valence radical cation salts with the AsF6 and SbF6 anions formulated as (TM-BEDT-TTF)2XF6 (X = As, Sb). Electrical conductivity was only found in one charge transfer complex, while the radical cation salts are all semiconducting.

Graphical abstract: Charge transfer complexes and radical cation salts of chiral methylated organosulfur donors

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Publication details

The article was received on 12 Dec 2013, accepted on 16 Feb 2014 and first published on 17 Feb 2014


Article type: Paper
DOI: 10.1039/C3CE42539H
Citation: CrystEngComm, 2014,16, 3906-3916
  • Open access: Creative Commons BY-NC license
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    Charge transfer complexes and radical cation salts of chiral methylated organosulfur donors

    S. Yang, F. Pop, C. Melan, A. C. Brooks, L. Martin, P. Horton, P. Auban-Senzier, G. L. J. A. Rikken, N. Avarvari and J. D. Wallis, CrystEngComm, 2014, 16, 3906
    DOI: 10.1039/C3CE42539H

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