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

doi:10.1063/1.3519557

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 journal › Article › peer-review

18 Scopus citations

Abstract

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 language	English (US)
Article number	234707
Journal	JOURNAL OF CHEMICAL PHYSICS
Volume	133
Issue number	23
DOIs	https://doi.org/10.1063/1.3519557
State	Published - Dec 21 2010

ASJC Scopus subject areas

General Physics and Astronomy
Physical and Theoretical Chemistry

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

abstract = "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.",

author = "Jongweon Cho and L. Berbil-Bautista and Niv Levy and Daniel Poulsen and Fr{\'e}chet, {Jean M.J.} and Crommie, {Michael F.}",

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.",

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AU - Cho, Jongweon

AU - Berbil-Bautista, L.

AU - Levy, Niv

AU - Poulsen, Daniel

AU - Fréchet, Jean M.J.

AU - Crommie, Michael F.

N1 - 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.

PY - 2010/12/21

Y1 - 2010/12/21

N2 - 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.

AB - 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.

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

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