Building conjugated organic structures on Si(111) surfaces via microwave-assisted Sonogashira coupling.
A novel step-by-step method employing microwave-assisted Sonogashira coupling is developed to grow fully conjugated organosilicon structures. As the first case study, p-(4-bromophenyl)acetylene is covalently conjugated to a p-(4-iodophenyl)acetylene-derived monolayer on a Si(111) surface. By bridging the two aromatic rings with C[triple bond]C, the pregrown monolayer is structurally extended outward from the Si surface, forming a fully conjugated (p-(4-bromophenylethynyl)phenyl)vinylene film. The film growth process, which reaches 90% yield after 2 h, is characterized thoroughly at each step by using X-ray reflectivity (XRR), X-ray standing waves (XSW), and X-ray fluorescence (XRF). The high yield and short reaction time offered by microwave-assisted surface Sonogashira coupling chemistry make it a promising strategy for functionalizing Si surfaces.
Department of Materials Science and Engineering, Northwestern University, Evanston, Illinois 60208, USA.
Jui-Ching
JC
Lin
Jun-Hyun
JH
Kim
Joshua A
JA
Kellar
Mark C
MC
Hersam
SonBinh T
ST
Nguyen
Michael J
MJ
Bedzyk
D008872:Microwaves; D009930:Organic Chemicals / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*; D014965:X-Rays
D009930:Organic Chemicals; D012825:Silicon