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Issue 9, 2016
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Structure–function relationships in single molecule rectification by N-phenylbenzamide derivatives

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Abstract

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.

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

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Publication details

The article was received on 17 Mar 2016, accepted on 24 Jun 2016 and first published on 30 Jun 2016


Article type: Paper
DOI: 10.1039/C6NJ00870D
Citation: New J. Chem., 2016,40, 7373-7378
  • Open access: Creative Commons BY-NC license
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    Structure–function relationships in single molecule rectification by N-phenylbenzamide derivatives

    C. Koenigsmann, W. Ding, M. Koepf, A. Batra, L. Venkataraman, C. F. A. Negre, G. W. Brudvig, R. H. Crabtree, V. S. Batista and C. A. Schmuttenmaer, New J. Chem., 2016, 40, 7373
    DOI: 10.1039/C6NJ00870D

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