Functionalization, self-assembly, and photoswitching quenching for azobenzene derivatives adsorbed on Au(111)

Jongweon Cho, L. Berbil-Bautista, Niv Levy, Daniel Poulsen, Jean M.J. Fréchet, Michael F. Crommie

    Research output: Contribution to journalArticlepeer-review

    18 Scopus citations


    We have used scanning tunneling microscopy to investigate the structure and photoswitching behavior of azobenzene molecules functionalized with bulky spacer groups and adsorbed onto Au(111). We find that positioning tert-butyl legs in a canted arrangement on the azobenzene phenyl rings quenches photoisomerizability of the molecule on Au(111). Addition of cyano groups at the para positions changes the molecular self-assembly significantly, but does not alter the quenched photoisomerizability. This behavior likely arises from a combination of molecule-surface interactions, molecule-molecule interactions, and alteration of azobenzene electronic structure resulting from the position-specific addition of tert-butyl groups.

    Original languageEnglish (US)
    Article number234707
    Issue number23
    StatePublished - Dec 21 2010

    Bibliographical note

    Funding Information:
    We are grateful to M. J. Comstock for helpful discussions. Molecular synthesis and STM measurements were supported by the Director, Office of Science, Office of Basic Energy Sciences, Division of Materials Sciences and Engineering Division, U.S. Department of Energy under Contract No. DE-AC03-76SF0098; STM data analysis was supported by the National Science Foundation within the Center of Integrated Nanomechanical Systems, under Grant No. EEC-0425941.

    ASJC Scopus subject areas

    • General Physics and Astronomy
    • Physical and Theoretical Chemistry


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