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.

Abstract

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.

Citation

Perepichka, D., Kondratenko, M., & Bryce, M. (2005). Self-assembly and multistage redox chemistry of strong electron acceptors on metal surfaces: Polynitrofluorenes on gold and platinum. Langmuir, 21(19), 8824-8831

• 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