IN SEARCH OF MOLECULAR RECTIFIERS - THE DONOR-SIGMA-ACCEPTOR SYSTEM DERIVED FROM TRIPTYCENEQUINONE AND TETRATHIAFULVALENE

Authors
SCHEIB S CAVA MP BALDWIN JW METZGER RM
Citation
S. Scheib et al., IN SEARCH OF MOLECULAR RECTIFIERS - THE DONOR-SIGMA-ACCEPTOR SYSTEM DERIVED FROM TRIPTYCENEQUINONE AND TETRATHIAFULVALENE, Journal of organic chemistry, 63(4), 1998, pp. 1198-1204
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
4
Year of publication
1998
Pages
1198 - 1204
Database
ISI
SICI code
0022-3263(1998)63:4<1198:ISOMR->2.0.ZU;2-Z
Abstract
Several donor-sigma-acceptor compounds (8, 9, 13, and 14) have been sy nthesized that contain a sterically hindered quinone tethered by a tet ramethylene chain to a substituted tetrathiafulvalene. Compounds 13 an d 14 show a dramatic increase (approximate to 450 mV) in the oxidation potential of the dipyrrolo-TTF unit, suggestive of considerable elect ron withdrawal through the sigma-bridge. Monolayers of 9 and 14 are me tastable at the air-water interface.