In-plane enyne metathesis and subsequent Diels-Alder reactions on self-assembled monolayers.
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.
Lee
Jungkyu K
JK
Chi
Young Shik
YS
Lee
Joon Sung
JS
Kim
Yang-Gyun
YG
Jung
Young Hwan
YH
Oh
Eugene
E
Ko
Sung-Bo
SB
Jung
Hyuk-Jun
HJ
Kang
Pill-Seong
PS
Choi
Insung S
IS