Bis(trifluoromethyl)methylene Addition to Vinyl-Terminated SAMs: A Gas-Phase C–C Bond-Forming Reaction on a Surface | Zendy

Malgorzata Adamkiewicz | Zendy; David O′Hagan | Zendy; Georg Hähner | Zendy

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Bis(trifluoromethyl)methylene Addition to Vinyl-Terminated SAMs: A Gas-Phase C–C Bond-Forming Reaction on a Surface

Author(s) -

Malgorzata Adamkiewicz,

David O′Hagan,

Georg Hähner

Publication year - 2014

Publication title -

langmuir

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.042

H-Index - 333

eISSN - 1520-5827

pISSN - 0743-7463

DOI - 10.1021/la5011727

Subject(s) - trifluoromethyl , x ray photoelectron spectroscopy , methylene , chemistry , monolayer , hexafluoroacetone , self assembled monolayer , contact angle , cyclopropanation , surface modification , polymer chemistry , double bond , photochemistry , organic chemistry , materials science , chemical engineering , catalysis , biochemistry , alkyl , engineering , composite material

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.

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