title: Self-assembly and multistage redox chemistry of strong electron acceptors on metal surfaces: polynitrofluorenes on gold and platinum.
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.
authors.affiliation: Centre Energie, Materiaux et Telecommunications, Institut National de la Recherche Scientifique, Universite du Quebec, Varennes J3X 1S2, Canada. perepichka@emt.inrs.ca
authors.forename: Dmitrii F
authors.initials: DF
authors.lastname: Perepichka
authors.forename: Mykola
authors.initials: M
authors.lastname: Kondratenko
authors.forename: Martin R
authors.initials: MR
authors.lastname: Bryce
mesh_terms: D004563:Electrochemistry; D004583:Electrons; D005449:Fluorenes / Q000138:chemical synthesis / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D010984:Platinum / Q000737:chemistry*; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D012680:Sensitivity and Specificity; D012996:Solutions / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods; D013499:Surface Properties
chemical_list: D005449:Fluorenes; D009574:Nitro Compounds; D011108:Polymers; D012996:Solutions; D010984:Platinum; D006046:Gold