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Self-assembly and multistage redox chemistry of strong electron acceptors on metal surfaces: Polynitrofluorenes on gold and platinum

Perepichka, D.F.; Kondratenko, M.; Bryce, M.R.


D.F. Perepichka

M. Kondratenko


Nitrofluoren-9-one and nitrofluoren-9-dicyanomethylene electron acceptors 7, 8, and 11 functionalized with a terminal thioctic acid unit have been synthesized from 2,4,5,7-tetranitrofluorenone. The self-assembled monolayers (SAMs) of these compounds on gold, formed via gold-sulfur interaction, have been fully characterized by electrochemical, FTIR, ellipsometry, and contact angle measurements. Cyclic voltammetry of SAMs reveals two reversible single-electron reduction waves for fluorenone derivatives 7a,b and 11, and three single-electron reductions for the dicyanomethylene-fluorene 8b, providing the first observation of a radical trianion species in SAMs. The tendency of the thioctic anchor to form multilayers via disulfide links is noted.

Journal Article Type Article
Publication Date 2005-09
Journal Langmuir
Print ISSN 0743-7463
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 21
Issue 19
Pages 8824-8831
Public URL