title: Epoxy-terminated self-assembled monolayers containing internal urea or amide groups.
abstract: We report the synthesis of new coupling agents with internal amide or urea groups possessing an epoxy-terminal group and trimethoxysilyl-anchoring group. The structural characterizations of the corresponding self-assembled monolayers (SAMs) were performed by polarization modulation infrared reflection adsorption spectroscopy (PM-IRRAS). The molecular assembly is mainly based on the intermolecular hydrogen-bonding between adjacent amide or urea groups in the monolayers. Because of the steric hindrance of amide or urea groups, the distance between the alkyl chains is too large to establish van der Waals interactions, inducing their disorder. The reactivity of the epoxy-terminal groups was successfully investigated through reaction with a fluorescent probe. We show that SAMs containing internal urea or amide groups exhibited a higher density of accessible epoxide groups than the corresponding long-chain (C22) glycidyl-terminated SAM.
authors: ISM, UMR 5255 CNRS, Université de Bordeaux , 351 cours de la Liberation CS 10004, 33 405 Talence, France.
authors: Michaël A
authors: MA
authors: Ramin
authors: Gwénaëlle
authors: G
authors: Le Bourdon
authors: Karine
authors: K
authors: Heuzé
authors: Marie
authors: M
authors: Degueil
authors: Thierry
authors: T
authors: Buffeteau
authors: Bernard
authors: B
authors: Bennetau
authors: Luc
authors: L
authors: Vellutini
mesh_terms: D000577:Amides / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D006860:Hydrogen Bonding; D012825:Silicon / Q000737:chemistry; D014508:Urea / Q000737:chemistry*
chemical_list: D000577:Amides; D004852:Epoxy Compounds; D014508:Urea; D012825:Silicon