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

Malgorzata Adamkiewicz; David O'Hagan; Georg Hähner

doi:10.1021/la5011727

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

Malgorzata Adamkiewicz, David O'Hagan^*, Georg Hähner^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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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.

Original language	English
Pages (from-to)	5422–5428
Number of pages	7
Journal	Langmuir
Volume	30
Issue number	19
Early online date	29 Apr 2014
DOIs	https://doi.org/10.1021/la5011727
Publication status	Published - 20 May 2014

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10.1021/la5011727Licence: CC BY

OHagen_2014_Langmuir_Bis
© 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
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Modification of silicon substrates: Modification of Silicon Oxide Substrates with Functional Ultrthin Organic Films
Haehner, G. (PI) & Smith, A. D. (CoI)
EPSRC
31/03/13 → 30/04/16
Project: Standard
SPIRIT/SINAPSE Studentship with Edin Uni: SPIRIT/SINAPSE Studentship with the University of Edinburgh
O'Hagan, D. (PI)
Scottish Funding Council
1/04/10 → 31/12/13
Project: Studentship
HorizonCF: EU ERC Advanced Grant - HorizonCF: New horizons in organo-fluorine chemistry
O'Hagan, D. (PI)
European Commission
1/01/10 → 31/12/14
Project: Standard

Georg Haehner
- gh23st-andrews.acuk
- School of Chemistry - Reader
- EaSTCHEM
Person: Academic

Cite this

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title = "Bis(trifluoromethyl)methylene addition to vinyl-terminated SAMs: a gas-phase C–C bond-forming reaction on a surface",

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.",

author = "Malgorzata Adamkiewicz and David O'Hagan and Georg H{\"a}hner",

note = "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{\textquoteright}H. acknowledges the European Research Council for an Advanced Grant and the Royal Society for a Wolfson Research Merit Award.",

year = "2014",

month = may,

day = "20",

doi = "10.1021/la5011727",

language = "English",

volume = "30",

pages = "5422–5428",

journal = "Langmuir",

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T2 - a gas-phase C–C bond-forming reaction on a surface

AU - Adamkiewicz, Malgorzata

AU - O'Hagan, David

AU - Hähner, Georg

N1 - 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.

PY - 2014/5/20

Y1 - 2014/5/20

N2 - 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.

AB - 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.

U2 - 10.1021/la5011727

DO - 10.1021/la5011727

M3 - Article

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JO - Langmuir

JF - Langmuir

IS - 19

ER -

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

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Projects

Modification of silicon substrates: Modification of Silicon Oxide Substrates with Functional Ultrthin Organic Films

SPIRIT/SINAPSE Studentship with Edin Uni: SPIRIT/SINAPSE Studentship with the University of Edinburgh

HorizonCF: EU ERC Advanced Grant - HorizonCF: New horizons in organo-fluorine chemistry

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Georg Haehner

Cite this