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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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Supplementary files

Article information


Submitted
17 Mar 2016
Accepted
24 Jun 2016
First published
30 Jun 2016

This article is Open Access

New J. Chem., 2016,40, 7373-7378
Article type
Paper

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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