title: Loosely packed self-assembled monolayer of N-hexadecyl-3,6-di(p-mercaptophenylacetylene)carbazole on gold and its application in biomimetic membrane research.
abstract: Dithiols of N-hexadecyl-3,6-di(p-mercaptophenylacetylene)carbazole (HDMC) have been synthesized and employed to form self-assembled monolayers (SAMs) on gold. One characteristic of the HDMC molecule is its peculiar molecular structure consisting of a large and rigid headgroup and a small and flexible alkyl-chain tail. HDMC adsorbates can attach to gold substrates by a strong Au-S bond with weak van der Waals interactions between the alkyl-chain tails, leading to a loosely packed hydrophobic SAM. In this way we can couple hybrid bilayer membranes (HBMs) to gold surfaces with more likeness to a cell bilayer than the conventional HBMs based on densely packed long-chain alkanethiol SAMs. The insulating properties and stability of the HDMC monolayer as well as the HDMC/lipid bilayer on gold have been investigated by electrochemical techniques including cyclic voltammetry and impedance spectroscopy. To test whether the quality of the bilayer is sufficiently high for biomimetic research, we incorporated the pore-forming protein alpha-hemolysin) and the horseradish peroxidase into the bilayers, respectively. Experimental results demonstrated that this type of loosely packed hydrophobic SAM has great potential in biomimetic bilayer research and biosensor application.
authors.affiliation: State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Jilin 130022, People's Republic of China.
authors.forename: Haifeng
authors.initials: H
authors.lastname: Bao
authors.forename: Zhangquan
authors.initials: Z
authors.lastname: Peng
authors.forename: Erkang
authors.initials: E
authors.lastname: Wang
authors.forename: Shaojun
authors.initials: S
authors.lastname: Dong
mesh_terms: D040761:Biomimetic Materials / Q000737:chemistry*; D002227:Carbazoles / Q000737:chemistry*; D004563:Electrochemistry; D006046:Gold / Q000737:chemistry*; D008051:Lipid Bilayers / Q000737:chemistry; D008567:Membranes, Artificial; D010713:Phosphatidylcholines / Q000737:chemistry; D011506:Proteins / Q000737:chemistry; D013057:Spectrum Analysis / Q000379:methods; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013499:Surface Properties
chemical_list: D002227:Carbazoles; D008051:Lipid Bilayers; D008567:Membranes, Artificial; C510525:N-hexadecyl-3,6-di(p-mercaptophenylacetylene)carbazole; D010713:Phosphatidylcholines; D011506:Proteins; D013438:Sulfhydryl Compounds; C480658:didecanoylphosphatidylcholine; D006046:Gold