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Influence of chromophore length and acceptor groups on the optical properties of rigidified merocyanine dyes

: Kreß, K.C.; Fischer, T.; Stumpe, J.; Frey, W.; Raith, M.; Beiraghi, O.; Eichhorn, S.H.; Tussetschläger, S.; Laschat, S.


ChemPlusChem 79 (2014), Nr.2, S.223-232
ISSN: 2192-6506
Fraunhofer IAP ()

Three series of rigidified tri-, penta- and heptamethine merocyanine dyes were synthesised. A piperidyl moiety was chosen as the electron-donating substituent while the electron-accepting group was varied from ketones to malononitriles and cyanoacetates. The structures of the compounds in the solid state and in solution were elucidated by X-ray diffraction and NMR spectroscopy, respectively, while optical properties were investigated by absorption and emission spectroscopy. As a general trend, the acceptor properties decrease in the series malononitrile>cyanoacetate>ketone based on the analysis of their solvatochromic behaviour. The experimental results were further supported by calculations at the B3LYP 6-311+G(d) level of theory.