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Citation: Zhang Hao-Li, Zhang Jin, Zhao Jiang, Wang Yong-Qiang, She Jin, Yu Hua-Zhong, Li Hu-Lin, Liu Zhong-Fan. New Approach on the Synthesis of Functionalized Alkanethiols and the Structural Characterization of Their Self-Assembled Monolayers[J]. Acta Physico-Chimica Sinica, ;1997, 13(06): 515-524. doi: 10.3866/PKU.WHXB19970608 shu

New Approach on the Synthesis of Functionalized Alkanethiols and the Structural Characterization of Their Self-Assembled Monolayers

1.
Center for Intelligent Materials Research(CIMR),College of Chemistry and Molecular Engineering,Peking University,Beijing 100871

Received Date: 22 October 1996
Available Online: 15 June 1997

A simple and general method for synthesizing functionalized alkanethiols is reported. The synthesis started from carboxylic acid, RCOOH, which was selectively condensed with the amino group of 2-aminoethanethiol, thus giving the targetting thiol compounds. A series of thiol compounds having a structure of RC(O)NHCH2CH2SH, where R was azobenzene derivatives, dicetylene derivatives and n-akanes, respectively, have been synthesized using this method. The self-assembled monolayers(SAMs) of these species were characterized by wettability measurement, electrochemistry and grazing incidence refletance infrared spectroscopy(GIR-IR). The SAM from 4((N-(2’-mercaptrvethyl)amino)carbonyl) azobenzene showed clearcut electrochemical reactivity in aqueous solution, in which the surface coverage was evaluated to be 4.21×10-10mol•cm-2. On the other hand, for the thiols of R being n-alkanes, the packing structures became gradually improved with increasing the alkyl chain length. For CH3(CH2)6C(O)NHCH2CH2SH SAM, GIR-IR data indicate that the C=O and N-H groups are parallel with the substrate surface while the whole molecular axis is perpendicular to the surface.
- Self-assembled monolayers(SAMs),
- Thiols,
- Azobenzene derivative,
- Diacetylene derivative,
- Contact angle measurement;Electrochemistry,
- Grazing incidence reflectance infrared spectroscopy(GIR-IR)
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