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.
| Original language | English |
|---|---|
| Pages (from-to) | 7373-7378 |
| Number of pages | 6 |
| Journal | New Journal of Chemistry |
| Volume | 40 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 2016 |
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ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Materials Chemistry
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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.
In: New Journal of Chemistry, Vol. 40, No. 9, 2016, p. 7373-7378.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Structure-function relationships in single molecule rectification by
T2 - N -phenylbenzamide derivatives
AU - Koenigsmann, Christopher
AU - Ding, Wendu
AU - Koepf, Matthieu
AU - Batra, Arunabh
AU - Venkataraman, Latha
AU - Negre, Christian F A
AU - Brudvig, Gary W
AU - Crabtree, Robert H.
AU - Batista, Victor S.
AU - Schmuttenmaer, Charles A.
PY - 2016
Y1 - 2016
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84984939512&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84984939512&partnerID=8YFLogxK
U2 - 10.1039/c6nj00870d
DO - 10.1039/c6nj00870d
M3 - Article
AN - SCOPUS:84984939512
VL - 40
SP - 7373
EP - 7378
JO - New Journal of Chemistry
JF - New Journal of Chemistry
SN - 1144-0546
IS - 9
ER -