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TitleGeometry and bond-length alternation in nonlinear optical materials. III. Structural parameters of two chromophores containing aromatizable donors
Publication TypeJournal Article
Year of Publication2008
AuthorsGainsford, G.J., Bhuiyan M.D.H., and Kay A.J.
JournalActa Crystallographica Section C: Crystal Structure Communications
Paginationo616 - o619
Date Published2008
ISSN01082701 (ISSN)
Keywords2 (3 cyano 4 (3 (1 decyl 1,4 dihydroquinolin 4 ylidene)prop 1 enyl) 5,5 dimethyl 2,5 dihydrofuran 2 ylidene)malononitrile, 2 (3 cyano 5 (3 (1 decyl 1,4 dihydroquinolin 4 ylidene)penta 1,3 dienyl) 5,5 dimethyl 2,5 dihydrofuran 2 ylidene)malononitrile, 2-(3-cyano-4-(3-(1-decyl-1,4-dihydroquinolin-4-ylidene)prop-1-enyl)-5,5-dimethyl-2,5-dihydrofuran-2-ylidene)malononitrile, 2-(3-cyano-5-(3-(1-decyl-1,4-dihydroquinolin-4-ylidene)penta-1,3-dienyl)-5,5-dimethyl-2,5-dihydrofuran-2-ylidene)malononitrile, Agglomeration, Alkyl chains, article, Bond length, chemical structure, chemistry, Chromophores, Clupeidae, Crystallography, X-Ray, Delocalization, isomerism, Isomers, light related phenomena, Malononitrile, Models, Molecular, Molecular aggregations, Molecular Structure, nitrile, Nitriles, Noncentrosymmetric, Nonlinear optical materials, Nonlinear optical responses, Optical materials, Optical Phenomena, Organic compounds, Polyene chains, quinoline derivative, Quinolines, Rotational isomers, Structural parameters, synthesis, Three dimensional, X ray crystallography
AbstractThe planar component of 2-{3-cyano-4-[3-(1-decyl-1,4-dihydro-quinolin-4-yl- idene)prop-1-enyl]-5,5-dimethyl-2,5-di-hydrofuran-2-yl-idene}malononitrile, C32H46N4O, (I), forms into layers parallel to the ( 01) plane. The larger of the two spaces between layers is filled by the alkyl chains, giving a 'sandwich stack' appearance. The packing of 2-{3-cyano-4-[5-(1-decyl-1,4-dihydro-quinolin- 4-yl-idene)penta-1,3-dienyl]-5,5-dimethyl-2,5-dihydro-furan-2-yl-idene} malononitrile, C34H38N4O, (II), which has partial disorder in the 1-decyl group, utilizes weak C - H⋯N, C - H⋯O and C - N⋯π inter-actions in a three-dimensional 'herring-bone' array with mol-ecular segments parallel to the (111) and ( 1 ) planes. Different rotational isomers with respect to the polyene chain and the 5,5-dimethyl-2,5-dihydro-furan-2-yl- idene link are observed in the two structures. The significance of the study lies in the delocalization of charge along the polyene chain and the supra-molecular aggregation present, which highlight the difficulty in obtaining the noncentrosymmetric alignment required for high nonlinear optical (NLO) responses in zwitterionic chromophores. © 2008 International Union of Crystallography.

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