trans-4,4‘-Dichloro-1,1‘,2,2‘,3,3‘-tetrathiadiazafulvalene (DC-TAF) and Its 1:1 Radical Cation Salts [DC-TAF][X]: Preparation and Solid-State Properties of BF4-, ClO4-, and FSO3- Derivatives
T. M. Barclay
1
,
L. Beer
1
,
A. W. Cordes
1
,
R. C. Haddon
1
,
M I Itkis
1
,
Richard Oakley
1
,
R. W. Reed
1
Publication type: Journal Article
Publication date: 1999-06-30
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Reductive coupling of 4,5-dichloro-1,2,3-dithiazolylium chloride yields trans-4,4‘-dichloro-1,1‘,2,2‘,3,3‘-tetrathiadiazafulvalene (DC-TAF), the first example of this heterofulvalene system. Ab initio molecular orbital (B3LYP/6-31G**) calculations on prototypal TAF confirm that the closed shell 1Ag state lies 22 kcal mol-1 below the 3Bu diradical triplet. Cyclic voltammetry on DC-TAF reveals two reversible oxidation waves at 0.80 and 1.25 V (in CH3CN, reference SCE). The ESR signal (g = 2.0117) of the radical cation [DC-TAF]+ (in SO2(l)) exhibits a five-line hyperfine coupling pattern with aN = 0.096 mT. DC-TAF forms a series of 1:1 radical ion salts [DC-TAF][X] by electrooxidation in the presence of tetrahedral counterions (X- = BF4-, ClO4-, FSO3-). The crystal structures of these salts are isomorphous, monoclinic space group P21/n, and consist of one-dimensional ladder-like arrays of [DC-TAF]+ radical cations bridged by S- - -S contacts ranging from 3.5 to 3.7 A. Variable-temperature conductivity and ma...
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Barclay T. M. et al. trans-4,4‘-Dichloro-1,1‘,2,2‘,3,3‘-tetrathiadiazafulvalene (DC-TAF) and Its 1:1 Radical Cation Salts [DC-TAF][X]: Preparation and Solid-State Properties of BF4-, ClO4-, and FSO3- Derivatives // Journal of the American Chemical Society. 1999. Vol. 121. No. 28. pp. 6657-6663.
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Barclay T. M., Beer L., Cordes A. W., Haddon R. C., Itkis M. I., Oakley R., Preuss K. E., Reed R. W. trans-4,4‘-Dichloro-1,1‘,2,2‘,3,3‘-tetrathiadiazafulvalene (DC-TAF) and Its 1:1 Radical Cation Salts [DC-TAF][X]: Preparation and Solid-State Properties of BF4-, ClO4-, and FSO3- Derivatives // Journal of the American Chemical Society. 1999. Vol. 121. No. 28. pp. 6657-6663.
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TY - JOUR
DO - 10.1021/ja990933z
UR - https://doi.org/10.1021/ja990933z
TI - trans-4,4‘-Dichloro-1,1‘,2,2‘,3,3‘-tetrathiadiazafulvalene (DC-TAF) and Its 1:1 Radical Cation Salts [DC-TAF][X]: Preparation and Solid-State Properties of BF4-, ClO4-, and FSO3- Derivatives
T2 - Journal of the American Chemical Society
AU - Barclay, T. M.
AU - Beer, L.
AU - Cordes, A. W.
AU - Haddon, R. C.
AU - Itkis, M I
AU - Oakley, Richard
AU - Preuss, Kathryn E.
AU - Reed, R. W.
PY - 1999
DA - 1999/06/30
PB - American Chemical Society (ACS)
SP - 6657-6663
IS - 28
VL - 121
SN - 0002-7863
SN - 1520-5126
ER -
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@article{1999_Barclay,
author = {T. M. Barclay and L. Beer and A. W. Cordes and R. C. Haddon and M I Itkis and Richard Oakley and Kathryn E. Preuss and R. W. Reed},
title = {trans-4,4‘-Dichloro-1,1‘,2,2‘,3,3‘-tetrathiadiazafulvalene (DC-TAF) and Its 1:1 Radical Cation Salts [DC-TAF][X]: Preparation and Solid-State Properties of BF4-, ClO4-, and FSO3- Derivatives},
journal = {Journal of the American Chemical Society},
year = {1999},
volume = {121},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/ja990933z},
number = {28},
pages = {6657--6663},
doi = {10.1021/ja990933z}
}
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Barclay, T. M., et al. “trans-4,4‘-Dichloro-1,1‘,2,2‘,3,3‘-tetrathiadiazafulvalene (DC-TAF) and Its 1:1 Radical Cation Salts [DC-TAF][X]: Preparation and Solid-State Properties of BF4-, ClO4-, and FSO3- Derivatives.” Journal of the American Chemical Society, vol. 121, no. 28, Jun. 1999, pp. 6657-6663. https://doi.org/10.1021/ja990933z.