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Matrix dependence of blue light emission from a novel NH2-functionalized dicyanoquinodimethane derivative.

Szablewski, Marek and Bloor, D. and Kagawa, Y. and Mosurkal, R. and Cole, J.M. and Clark, S.J. and Cross, G.H. and Palsson, L.O. (2006) 'Matrix dependence of blue light emission from a novel NH2-functionalized dicyanoquinodimethane derivative.', Journal of physical organic chemistry., 19 (3). pp. 206-213.


The reactions of primary and secondary amines with (cyclohexa-2,5-diene-1,4-diylidene)-dimalononitrile (TCNQ) lead to mono- and disubstituted dicyanoquinodimethane derivatives and fluorescence emission has been observed for several of these compounds. We report the luminescence properties, synthesis and crystal structure of the novel dicyanoquinodimethane derivative 2-{4-[amino-(2,6-dimethyl-morpholin-4-yl)-methylene]-cyclohexa-2,5- dienylidene}-malononitrile (Ammor), a unique example of an asymmetric dicyanoquinodimethane derivative in which one of the nitrile groups has been replaced with an NH2 moiety, which provides a reactive centre for potential further substitution or tethering to larger molecules or polymers. The luminescence properties of the title compound were investigated in a variety of environments, including alcohol solutions at room temperature and a glass-forming solvent at low temperature. The fluorescence quantum yields and Stokes' shifts of the blue emission were found to be very sensitive to the matrix. The crystal structure of the subject compound was determined, revealing that the molecules are non-planar in the ground state. The environmentally sensitive emission is discussed in terms of the conformational change during photoexcitation and the constraint imposed on this by the matrix. This behaviour is also compared with that of other related amino-functionalized dicyanoquinodimethane derivatives.

Item Type:Article
Keywords:TCNQ, Matrix-dependent fluorescence, Nonlinear-optical applications, Anion-radical derivatives, Pull quinonoid compounds, Fast acid violet-2R, Substituted quinodimethans, Internal-conversion, Crystal-structures, Solvent polarity, Rhodamine dye.
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Record Created:12 Aug 2011 12:20
Last Modified:18 Nov 2014 12:44

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