In-plane enyne metathesis and subsequent Diels-Alder reactions on self-assembled monolayers

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We report in-plane enyne metathesis and subsequent Diels-Alder reactions on self-assembled monolayers (SAMs) terminating in vinyl and acetylenyl groups on gold. After the formation of SAMs of vinyl and acetylenyl group-containing dithiols on gold, in-plane enyne metathesis of the vinyl and acetylenyl groups, leading to the formation of 1,3-diene, was achieved on the SAMs, and Diels-Alder reactions were then successfully performed with tetracyanoethylene, maleic anhydride, and maleimide. The reactions were confirmed by FT-IR spectroscopy, X-ray photoelectron spectroscopy, and time-of-flight secondary-ion mass spectrometry. In-plane enyne metathesis developed herein would offer a versatile platform for the functionalization of surfaces with mild reaction conditions and a high compatibility in functional groups.
Publisher
AMER CHEMICAL SOC
Issue Date
2005-11
Language
English
Article Type
Article
Keywords

TRANSFER RADICAL POLYMERIZATION; CROSS-METATHESIS; ELECTRODE SURFACES; GOLD; AU(111); IMMOBILIZATION; WETTABILITY; DERIVATIVES; DISULFIDES; REACTIVITY

Citation

LANGMUIR, v.21, no.23, pp.10311 - 10315

ISSN
0743-7463
DOI
10.1021/la051680s
URI
http://hdl.handle.net/10203/90767
Appears in Collection
CH-Journal Papers(저널논문)
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