Ramin Michaël A, Le Bourdon Gwénaëlle, Heuzé Karine, Degueil Marie, Buffeteau Thierry, Bennetau Bernard, Vellutini Luc
ISM, UMR 5255 CNRS, Université de Bordeaux , 351 cours de la Liberation CS 10004, 33 405 Talence, France.
Langmuir. 2015 Mar 10;31(9):2783-9. doi: 10.1021/la5049375. Epub 2015 Feb 24.
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.
我们报道了具有内部酰胺或脲基、环氧端基和三甲氧基硅烷基锚定基团的新型偶联剂的合成。通过偏振调制红外反射吸附光谱（PM-IRRAS）对相应的自组装单分子层（SAMs）进行了结构表征。分子组装主要基于单分子层中相邻酰胺或脲基之间的分子间氢键。由于酰胺或脲基的空间位阻，烷基链之间的距离过大，无法建立范德华相互作用，导致它们无序排列。通过与荧光探针反应，成功研究了环氧端基的反应活性。我们表明，含有内部脲或酰胺基团的SAMs比相应的长链（C22）缩水甘油基封端的SAM表现出更高密度的可及环氧基团。
