D.F. Perepichka
A (π-extended tetrathiafulvalene)-fluorene conjugate. Unusual electrochemistry and charge transfer properties: The first observation of a covalent D²⁺–σ–A˙⁻ redox state
Perepichka, D.F.; Bryce, M.R.; Perepichka, I.F.; Lyubchik, S.B.; Christensen, C.A.; Godbert, N.; Batsanov, A.S.; Levillain, E.; McInnes, E.J.L.; Zhao, J.P.
Authors
Professor Martin Bryce m.r.bryce@durham.ac.uk
Professor
I.F. Perepichka
S.B. Lyubchik
C.A. Christensen
N. Godbert
A.S. Batsanov
E. Levillain
E.J.L. McInnes
J.P. Zhao
Abstract
The synthesis of novel electrochemically amphoteric TTFAQ-sigma-A compounds (TTFAQ = 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene, sigma = saturated spacer, A = polynitrofluorene acceptor) is reported. Their solution redox behavior is characterized by three single-electron reduction and one two-electron oxidation waves. Electrochemical quasi reversibility of the TTFAQ(2+) state and a low E-ox - E-red gap (approximate to0.25 V) for 3-(9-dicyanomethylene-4,5,7-trinitrofluorene-2-sulfonyl)-propionic acid 2-[10-(4,5-dimethyl-[1,3]dithiol-2-ylidene)-9,10-dihydroanthracen-9-ylid enel]-5-methyl-[1,3]dithiol-4-ylmethyI ester (10) has enabled the electrochemical generation of the hitherto unknown transient D2+-sigma-A(.-) state as observed in cyclic voltammetry and time-resolved spectroelectrochemistry. The ground state of compound 10 was shown to be ionic in the solid but is essentially neutral in solution (according to electron paramagnetic resonance). The X-ray structure of an intermolecular 1:2 complex between 2-[2,7-bis(2-hydroxyethoxy)-9,10-bis(4,5dimethyl-[1,3]dithiol-2-ylidene) -9,10-dihydroanthracene and 2,5,7-trinitro-4-bromo-9-dicyanomethylenefluorene, 14(.)(17)(2), reveals, for the first time, full electron transfer in a fluorene charge-transfer complex.
Citation
Perepichka, D., Bryce, M., Perepichka, I., Lyubchik, S., Christensen, C., Godbert, N., …Zhao, J. (2002). A (π-extended tetrathiafulvalene)-fluorene conjugate. Unusual electrochemistry and charge transfer properties: The first observation of a covalent D²⁺–σ–A˙⁻ redox state. Journal of the American Chemical Society, 124(47), 14227-14238. https://doi.org/10.1021/ja012518o
Journal Article Type | Article |
---|---|
Publication Date | Oct 1, 2002 |
Deposit Date | May 15, 2007 |
Journal | Journal of the American Chemical Society |
Print ISSN | 0002-7863 |
Electronic ISSN | 1520-5126 |
Publisher | American Chemical Society |
Peer Reviewed | Peer Reviewed |
Volume | 124 |
Issue | 47 |
Pages | 14227-14238 |
DOI | https://doi.org/10.1021/ja012518o |
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