双（三氟甲基）亚甲基加成到乙烯基封端的自组装单分子膜上：表面上的气相碳-碳键形成反应。

Bis(trifluoromethyl)methylene addition to vinyl-terminated SAMs: a gas-phase C-C bond-forming reaction on a surface.

作者信息

Adamkiewicz Malgorzata, O'Hagan David, Hähner Georg

机构信息

EaStCHEM School of Chemistry, University of St. Andrews , North Haugh, St. Andrews, Fife, KY16 9ST, U.K.

出版信息

Langmuir. 2014 May 20;30(19):5422-8. doi: 10.1021/la5011727. Epub 2014 May 8.

DOI:10.1021/la5011727

PMID:24806554

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4031204/

Abstract

Vinyl-terminated self-assembled monolayers (SAMs) on silicon oxide substrates were chemically modified by the addition of a bis(trifluoromethyl)methylene group in a rare gas-phase C-C bond-forming reaction to directly generate films carrying terminal CF3 groups. The vinyl-terminated films were treated with hexafluoroacetone azine (HFAA) for modification. The films were characterized with ellipsometry, contact angle measurements, atomic force microscopy (AFM), and X-ray photoelectron spectroscopy (XPS). In this study, we find that for optimized conditions clean reactions occur on a surface between SAMs with terminal olefins and HFAA, and the product is consistent with bis(trifluoromethyl)cyclopropanation formation after nitrogen extrusion.

摘要

通过在稀有气体相碳-碳键形成反应中添加双（三氟甲基）亚甲基，对氧化硅衬底上的乙烯基封端自组装单分子层（SAMs）进行化学修饰，以直接生成带有末端CF3基团的薄膜。用六氟丙酮嗪（HFAA）处理乙烯基封端的薄膜进行改性。通过椭偏仪、接触角测量、原子力显微镜（AFM）和X射线光电子能谱（XPS）对薄膜进行表征。在本研究中，我们发现，在优化条件下，末端烯烃的SAMs与HFAA在表面发生清洁反应，产物与脱氮后形成双（三氟甲基）环丙烷一致。