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

Abstract

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.

• Authors: Jungkyu K Lee, Young Shik Chi, Joon Sung Lee, Yang-Gyun Kim, Young Hwan Jung, Eugene Oh, Sung-Bo Ko, Hyuk-Jun Jung, Pill-Seong Kang, Insung S Choi
• Journal: Langmuir : the ACS journal of surfaces and colloids (Langmuir) Vol. 21 Issue 23 Pg. 10311-5 (Nov 08 2005) ISSN: 0743-7463 [Print] United States
• PMID: 16262283 (Publication Type: Letter)