Kreß Katharina Christina, Fischer Thomas, Stumpe Joachim, Frey Wolfgang, Raith Melanie, Beiraghi Omid, Eichhorn S Holger, Tussetschläger Stefan, Laschat Sabine
Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany), Fax: (+49) 771-685-64285.
Fraunhofer-Institut für Angewandte Polymerforschung, Bereich Funktionale Polymersysteme, Geiselbergstrasse 69, 14476 Potsdam-Golm (Germany), Fax: (+49) 331-568-3259.
Chempluschem. 2014 Feb;79(2):223-232. doi: 10.1002/cplu.201300308. Epub 2013 Nov 26.
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.
合成了三个系列的刚性化三、五和七甲川部花青染料。选择哌啶基部分作为供电子取代基，而吸电子基团则从酮类变化到丙二腈和氰基乙酸酯。分别通过X射线衍射和核磁共振光谱对固态和溶液状态下化合物的结构进行了阐明，同时通过吸收光谱和发射光谱对光学性质进行了研究。基于对它们的溶剂化显色行为的分析，作为一般趋势，在丙二腈>氰基乙酸酯>酮这个系列中受体性质降低。理论计算在B3LYP 6-311+G(d)水平进一步支持了实验结果。
