Joint experimental and theoretical characterization of the electronic structure of 4,4′-Bis(N-m-tolyl-N-phenylamino)biphenyl (TPD) and substituted derivatives

J. Cornil; N. E. Gruhn; D. A. Dos Santos; M. Malagoli; P. A. Lee; S. Barlow; S. Thayumanavan; S. R. Marder; N. R. Armstrong; J. L. Brédas

doi:10.1021/jp003142o

Joint experimental and theoretical characterization of the electronic structure of 4,4′-Bis(N-m-tolyl-N-phenylamino)biphenyl (TPD) and substituted derivatives

J. Cornil^*, N. E. Gruhn, D. A. Dos Santos, M. Malagoli, P. A. Lee, S. Barlow, S. Thayumanavan, S. R. Marder, N. R. Armstrong, J. L. Brédas

^*Corresponding author for this work

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50 Scopus citations

Abstract

We investigate by means of gas-phase ultraviolet photoelectron spectroscopy complemented by quantum-chemical calculations how the frontier levels of the 4,4′-bis(N-m-7tolyl-N-phenylamino)biphenyl (TPD) molecule are affected upon substitution of the terminal aryl rings with methoxy groups or fluorine atoms. These results provide strategies to modulate energy barriers at metal/organic or organic/organic interfaces involving TPD and its derivatives; it is shown that the change in the energy of the HOMO level of TPD upon derivatization is strongly affected by inductive effects taking place in the a skeleton.

Original language	English (US)
Pages (from-to)	5206-5211
Number of pages	6
Journal	Journal of Physical Chemistry A
Volume	105
Issue number	21
DOIs	https://doi.org/10.1021/jp003142o
State	Published - May 31 2001
Externally published	Yes

ASJC Scopus subject areas

Physical and Theoretical Chemistry

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Cornil, J., Gruhn, N. E., Dos Santos, D. A., Malagoli, M., Lee, P. A., Barlow, S., Thayumanavan, S., Marder, S. R., Armstrong, N. R., & Brédas, J. L. (2001). Joint experimental and theoretical characterization of the electronic structure of 4,4′-Bis(N-m-tolyl-N-phenylamino)biphenyl (TPD) and substituted derivatives. Journal of Physical Chemistry A, 105(21), 5206-5211. https://doi.org/10.1021/jp003142o

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title = "Joint experimental and theoretical characterization of the electronic structure of 4,4′-Bis(N-m-tolyl-N-phenylamino)biphenyl (TPD) and substituted derivatives",

abstract = "We investigate by means of gas-phase ultraviolet photoelectron spectroscopy complemented by quantum-chemical calculations how the frontier levels of the 4,4′-bis(N-m-7tolyl-N-phenylamino)biphenyl (TPD) molecule are affected upon substitution of the terminal aryl rings with methoxy groups or fluorine atoms. These results provide strategies to modulate energy barriers at metal/organic or organic/organic interfaces involving TPD and its derivatives; it is shown that the change in the energy of the HOMO level of TPD upon derivatization is strongly affected by inductive effects taking place in the a skeleton.",

author = "J. Cornil and Gruhn, {N. E.} and {Dos Santos}, {D. A.} and M. Malagoli and Lee, {P. A.} and S. Barlow and S. Thayumanavan and Marder, {S. R.} and Armstrong, {N. R.} and Br{\'e}das, {J. L.}",

year = "2001",

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doi = "10.1021/jp003142o",

language = "English (US)",

volume = "105",

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journal = "Journal of Physical Chemistry A",

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Cornil, J, Gruhn, NE, Dos Santos, DA, Malagoli, M, Lee, PA, Barlow, S, Thayumanavan, S, Marder, SR, Armstrong, NR & Brédas, JL 2001, 'Joint experimental and theoretical characterization of the electronic structure of 4,4′-Bis(N-m-tolyl-N-phenylamino)biphenyl (TPD) and substituted derivatives', Journal of Physical Chemistry A, vol. 105, no. 21, pp. 5206-5211. https://doi.org/10.1021/jp003142o

TY - JOUR

T1 - Joint experimental and theoretical characterization of the electronic structure of 4,4′-Bis(N-m-tolyl-N-phenylamino)biphenyl (TPD) and substituted derivatives

AU - Cornil, J.

AU - Gruhn, N. E.

AU - Dos Santos, D. A.

AU - Malagoli, M.

AU - Lee, P. A.

AU - Barlow, S.

AU - Thayumanavan, S.

AU - Marder, S. R.

AU - Armstrong, N. R.

AU - Brédas, J. L.

PY - 2001/5/31

Y1 - 2001/5/31

N2 - We investigate by means of gas-phase ultraviolet photoelectron spectroscopy complemented by quantum-chemical calculations how the frontier levels of the 4,4′-bis(N-m-7tolyl-N-phenylamino)biphenyl (TPD) molecule are affected upon substitution of the terminal aryl rings with methoxy groups or fluorine atoms. These results provide strategies to modulate energy barriers at metal/organic or organic/organic interfaces involving TPD and its derivatives; it is shown that the change in the energy of the HOMO level of TPD upon derivatization is strongly affected by inductive effects taking place in the a skeleton.

AB - We investigate by means of gas-phase ultraviolet photoelectron spectroscopy complemented by quantum-chemical calculations how the frontier levels of the 4,4′-bis(N-m-7tolyl-N-phenylamino)biphenyl (TPD) molecule are affected upon substitution of the terminal aryl rings with methoxy groups or fluorine atoms. These results provide strategies to modulate energy barriers at metal/organic or organic/organic interfaces involving TPD and its derivatives; it is shown that the change in the energy of the HOMO level of TPD upon derivatization is strongly affected by inductive effects taking place in the a skeleton.

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U2 - 10.1021/jp003142o

DO - 10.1021/jp003142o

M3 - Article

AN - SCOPUS:0035979138

SN - 1089-5639

VL - 105

SP - 5206

EP - 5211

JO - Journal of Physical Chemistry A

JF - Journal of Physical Chemistry A

IS - 21

ER -

Joint experimental and theoretical characterization of the electronic structure of 4,4′-Bis(N-m-tolyl-N-phenylamino)biphenyl (TPD) and substituted derivatives

Abstract

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