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, Neal R Armstrong, J. L. Brédas

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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 languageEnglish (US)
Pages (from-to)5206-5211
Number of pages6
JournalJournal of Physical Chemistry A
Volume105
Issue number21
DOIs
StatePublished - May 31 2001

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Temperature programmed desorption
Electronic structure
electronic structure
Derivatives
ultraviolet spectroscopy
musculoskeletal system
Ultraviolet photoelectron spectroscopy
fluorine
Fluorine
Energy barriers
photoelectron spectroscopy
substitutes
vapor phases
energy
rings
Substitution reactions
Gases
Metals
metals
atoms

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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Joint experimental and theoretical characterization of the electronic structure of 4,4′-Bis(N-m-tolyl-N-phenylamino)biphenyl (TPD) and substituted derivatives. / Cornil, J.; Gruhn, N. E.; Dos Santos, D. A.; Malagoli, M.; Lee, P. A.; Barlow, S.; Thayumanavan, S.; Marder, S. R.; Armstrong, Neal R; Brédas, J. L.

In: Journal of Physical Chemistry A, Vol. 105, No. 21, 31.05.2001, p. 5206-5211.

Research output: Contribution to journalArticle

Cornil, J. ; Gruhn, N. E. ; Dos Santos, D. A. ; Malagoli, M. ; Lee, P. A. ; Barlow, S. ; Thayumanavan, S. ; Marder, S. R. ; Armstrong, Neal R ; Brédas, J. L. / Joint experimental and theoretical characterization of the electronic structure of 4,4′-Bis(N-m-tolyl-N-phenylamino)biphenyl (TPD) and substituted derivatives. In: Journal of Physical Chemistry A. 2001 ; Vol. 105, No. 21. pp. 5206-5211.
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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, Neal R

AU - Brédas, J. L.

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