Bis(trifluoromethyl)methylene addition to vinyl-terminated SAMs : a gas-phase C–C bond-forming reaction on a surface
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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.
Adamkiewicz , M , O'Hagan , D & Hähner , G 2014 , ' Bis(trifluoromethyl)methylene addition to vinyl-terminated SAMs : a gas-phase C–C bond-forming reaction on a surface ' Langmuir , vol 30 , no. 19 , pp. 5422–5428 . DOI: 10.1021/la5011727
© 2014 American Chemical Society. Article published under Creative Commons CC-BY license (https://creativecommons.org/licenses/by/4.0/). Full terms can be found here: http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html
The authors acknowledge the Scottish Funding Council for a SPIRIT Studentship (M.A.) and the EPSRC (EP/K000411/1) for financial support, and D.O’H. acknowledges the European Research Council for an Advanced Grant and the Royal Society for a Wolfson Research Merit Award.
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