m-Terphenyl thiols: rigid and bulky molecules for the formation of bioactive self-assembled monolayers on gold.
The m-terphenyl 4-mercaptomethyl-2,6-diphenylbenzoic acid (3), was prepared and shown to form omega-carboxyl terminated self-assembled monolayers (SAMs) on gold with high surface pKa(10.1 +/- 0.2) and low density favourable for the binding of biological macromolecules.
Dickie
Diane A
DA
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada.
Chan
Andy Y C
AY
Jalali
Hanifa
H
Jenkins
Hilary A
HA
Yu
Hua-Zhong
HZ
Clyburne
Jason A C
JA
D015502:Absorptiometry, Photon; D001565:Benzoates / Q000138:chemical synthesis / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013499:Surface Properties
D001565:Benzoates; D009942:Organometallic Compounds; D013438:Sulfhydryl Compounds; C506104:m-terphenyl 4-mercaptomethyl-2,6-diphenylbenzoic acid; D006046:Gold