I.F. Perepichka
Electron acceptors of the fluorene series. Part 13. 9-(5- Nitrofuran-2-ylidene)- and 9-(5-nitro-2-thienylidene)-2,4,5,7- tetranitrofluorenes: novel pi-extended electron acceptors. Synthesis, cyclic voltammetry and X-ray crystal structures for the acceptor
Perepichka, I.F.; Perepichka, D.F.; Lyubchik, S.B.; Bryce, M.R.; Batsanov, A.S.; Howard, J.A.K.
Authors
D.F. Perepichka
S.B. Lyubchik
Professor Martin Bryce m.r.bryce@durham.ac.uk
Professor
Dr Andrei Batsanov a.s.batsanov@durham.ac.uk
Academic Visitor
Judith Howard j.a.k.howard@durham.ac.uk
Emeritus Professor
Abstract
Two novel polynitrofluorene acceptors pi -extended with 5- nitrofuran and 5-nitrothiophene moieties (2 and 3); have been synthesised. Cyclic voltammetry experiments show single electron reduction peaks at ca. -0.66-0.67 V (vs. Fc/Fc(+)); however, this process (probably due to substantial changes in geometry of reduced species) is electrochemically irreversible and re-oxidation of the derived radical anions is observed at +0.05 and -0.04 V, for 2 and 3, respectively. Electronic absorption spectroscopy confirms charge transfer complexation of the studied acceptor with 4,5-dimethyltetrathiafulvalene (Me2TTF) in solution. The X-ray crystal structure of the 1 : 1 charge transfer complex (CTC) of acceptor 2 with Me2TTF shows mixed A . . .D . . .A . . .D stacking, and its comparison with the structure of the acceptor itself indicates a neutral ground state of this CTC. Theoretical HF/6-31 G(d) calculations for the acceptor 2 and its radical anion and dianion states are in agreement with this conclusion. Intramolecular hydrogen bonding in 2 between the oxygen of the furan ring and C(8)-H hydrogen of the fluorene moiety is observed in both solution (H-1 NMR) and solid state (X-ray) and also supported by theoretical calculations.
Citation
Perepichka, I., Perepichka, D., Lyubchik, S., Bryce, M., Batsanov, A., & Howard, J. (2001). Electron acceptors of the fluorene series. Part 13. 9-(5- Nitrofuran-2-ylidene)- and 9-(5-nitro-2-thienylidene)-2,4,5,7- tetranitrofluorenes: novel pi-extended electron acceptors. Synthesis, cyclic voltammetry and X-ray crystal structures for the acceptor. Journal of the Chemical Society-Perkin Transactions 2, 2001(9), 1546-1551
| Journal Article Type | Article |
|---|---|
| Publication Date | 2001-09 |
| Journal | Journal of the Chemical Society, Perkin Transactions 2 |
| Print ISSN | 1470-1820 |
| Electronic ISSN | 2050-8247 |
| Peer Reviewed | Peer Reviewed |
| Volume | 2001 |
| Issue | 9 |
| Pages | 1546-1551 |
| Public URL | https://durham-repository.worktribe.com/output/1580344 |
| Publisher URL | <Go to ISI>://000171185600017 |