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Matrix dependence of light emission from TCNQ adducts

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

Matrix dependence of light emission from TCNQ adducts Thumbnail


D. Bloor

Y. Kagawa

M. Ravi

G.H. Cross

C. Parmer

G. Rumbles


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-yltetrahydropyrimidin-2(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.


Bloor, D., Kagawa, Y., Szablewski, M., Ravi, M., Clark, S., Cross, G., …Rumbles, G. (2001). Matrix dependence of light emission from TCNQ adducts. Journal of materials chemistry, 11(12), 3053-3062.

Journal Article Type Article
Publication Date Oct 31, 2001
Deposit Date Dec 19, 2006
Publicly Available Date Dec 15, 2014
Journal Journal of Materials Chemistry
Print ISSN 0959-9428
Electronic ISSN 1364-5501
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 11
Issue 12
Pages 3053-3062
Keywords Intramolecular charge-transfer, Pull quinonoid compounds, Excited-state, Solvent polarity, Polymers, Dyes, Solvatochromism, Photophysics, Alignment, Viscosity.


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