Matrix dependence of light emission from TCNQ adducts

D. Bloor, Y. Kagawa, M. Szablewski, M. Ravi, S. J. Clark, G. H. Cross, L. O. Pålsson, A. Beeby, C. Parmer, Gary Rumbles

Research output: Contribution to journalArticle

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Abstract

The reactions of primary and secondary amines with 7,7,8,8-tetracyano-p-quinodimethane§ (TCNQ) lead to mono- and di-substituted adducts. Fluorescence emission has been observed for several of these compounds. The luminescence property of the TCNQ adducts, 2-{4-[(2,6-dimethylmorpholin-4-yl)(4-methylpiperidin-1-yl) methylene]cyclohexa-2,5-dien-1-ylidene}malononitrile (MORPIP) and 2-{4-[cyclohex-1-yltetrahydropyrimidin2(1H)-ylidene]cyclohexa-2,5-dien-1- ylidene}malononitrile (AMINO) were investigated in a variety of environments. These included alcohol solutions and crystals at room temperature and glass forming solvents and polymer films as a function of temperature. The fluorescence quantum yields and Stokes' shifts were found to be very sensitive to the matrix. Crystal structure data show that the molecules are non-planar in the ground state. The matrix effect is discussed in terms of the conformational change during photo-excitation and the constraint imposed on this by the matrix.

Original languageEnglish
Pages (from-to)3053-3062
Number of pages10
JournalJournal of Materials Chemistry
Volume11
Issue number12
DOIs
Publication statusPublished - 2001

Fingerprint

Light emission
adducts
malononitrile
light emission
Fluorescence
Photoexcitation
Quantum yield
matrices
Polymer films
Ground state
Amines
Luminescence
fluorescence
Alcohols
Crystal structure
photoexcitation
methylene
Glass
Temperature
Crystals

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Materials Science(all)

Cite this

Bloor, D., Kagawa, Y., Szablewski, M., Ravi, M., Clark, S. J., Cross, G. H., ... Rumbles, G. (2001). Matrix dependence of light emission from TCNQ adducts. Journal of Materials Chemistry, 11(12), 3053-3062. https://doi.org/10.1039/b104992p

Matrix dependence of light emission from TCNQ adducts. / Bloor, D.; Kagawa, Y.; Szablewski, M.; Ravi, M.; Clark, S. J.; Cross, G. H.; Pålsson, L. O.; Beeby, A.; Parmer, C.; Rumbles, Gary.

In: Journal of Materials Chemistry, Vol. 11, No. 12, 2001, p. 3053-3062.

Research output: Contribution to journalArticle

Bloor, D, Kagawa, Y, Szablewski, M, Ravi, M, Clark, SJ, Cross, GH, Pålsson, LO, Beeby, A, Parmer, C & Rumbles, G 2001, 'Matrix dependence of light emission from TCNQ adducts', Journal of Materials Chemistry, vol. 11, no. 12, pp. 3053-3062. https://doi.org/10.1039/b104992p
Bloor D, Kagawa Y, Szablewski M, Ravi M, Clark SJ, Cross GH et al. Matrix dependence of light emission from TCNQ adducts. Journal of Materials Chemistry. 2001;11(12):3053-3062. https://doi.org/10.1039/b104992p
Bloor, D. ; Kagawa, Y. ; Szablewski, M. ; Ravi, M. ; Clark, S. J. ; Cross, G. H. ; Pålsson, L. O. ; Beeby, A. ; Parmer, C. ; Rumbles, Gary. / Matrix dependence of light emission from TCNQ adducts. In: Journal of Materials Chemistry. 2001 ; Vol. 11, No. 12. pp. 3053-3062.
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AU - Szablewski, M.

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AU - Clark, S. J.

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AU - Pålsson, L. O.

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AU - Rumbles, Gary

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AB - The reactions of primary and secondary amines with 7,7,8,8-tetracyano-p-quinodimethane§ (TCNQ) lead to mono- and di-substituted adducts. Fluorescence emission has been observed for several of these compounds. The luminescence property of the TCNQ adducts, 2-{4-[(2,6-dimethylmorpholin-4-yl)(4-methylpiperidin-1-yl) methylene]cyclohexa-2,5-dien-1-ylidene}malononitrile (MORPIP) and 2-{4-[cyclohex-1-yltetrahydropyrimidin2(1H)-ylidene]cyclohexa-2,5-dien-1- ylidene}malononitrile (AMINO) were investigated in a variety of environments. These included alcohol solutions and crystals at room temperature and glass forming solvents and polymer films as a function of temperature. The fluorescence quantum yields and Stokes' shifts were found to be very sensitive to the matrix. Crystal structure data show that the molecules are non-planar in the ground state. The matrix effect is discussed in terms of the conformational change during photo-excitation and the constraint imposed on this by the matrix.

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