Structure–function relationships in single molecule rectification by N-phenylbenzamide derivatives

Koenigsmann, Christopher; Ding, Wendu; Koepf, Matthieu; Batra, Arunabh; Venkataraman, Latha; Negre, Christian F. A.; Brudvig, Gary W.; Crabtree, Robert H.; Batista, Victor S.; Schmuttenmaer, Charles A.

doi:10.1039/C6NJ00870D

Structure–function relationships in single molecule rectification by N-phenylbenzamide derivatives

Journal Article · Thu Jun 30 00:00:00 EDT 2016 · New Journal of Chemistry

DOI:https://doi.org/10.1039/C6NJ00870D· OSTI ID:1341855

Koenigsmann, Christopher ^[1]; Ding, Wendu ^[2]; Koepf, Matthieu ^[3]; Batra, Arunabh ^[4]; Venkataraman, Latha ^[4]; Negre, Christian F. A. ^[5]; Brudvig, Gary W. ^[2]; Crabtree, Robert H. ^[2]; Batista, Victor S. ^[2]; Schmuttenmaer, Charles A. ^[2]

Yale Univ., West Haven, CT (United States); Fordham Univ., Bronx, NY (United States)
Yale Univ., West Haven, CT (United States); Yale Univ., New Haven, CT (United States)
Yale Univ., West Haven, CT (United States)
Columbia Univ., New York, NY (United States)
Yale Univ., West Haven, CT (United States); Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

Here, we examine structure–function relationships in a series of N-phenylbenzamide (NPBA) derivatives by using computational modeling to identify molecular structures that exhibit both rectification and good conductance together with experimental studies of bias-dependent single molecule conductance and rectification behavior using the scanning tunneling microscopy break-junction technique. From a large number of computationally screened molecular diode structures, we have identified NPBA as a promising candidate, relative to the other structures that were screened. We demonstrate experimentally that conductance and rectification are both enhanced by functionalization of the NPBA 4-carboxamido-aniline moiety with electron donating methoxy groups, and are strongly correlated with the energy of the conducting frontier orbital relative to the Fermi level of the gold leads used in break-junction experiments.

View Accepted Manuscript (DOE)

Research Organization:: Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC52-06NA25396

OSTI ID:: 1341855

Report Number(s):: LA-UR--15-28629

Journal Information:: New Journal of Chemistry, Journal Name: New Journal of Chemistry Journal Issue: 9 Vol. 40; ISSN NJCHE5; ISSN 1144-0546

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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