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New push-pull dyes based on 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)malononitrile: An amine-directed synthesis
Dyes and Pigments ( IF 4.1 ) Pub Date : 2020-01-07 , DOI: 10.1016/j.dyepig.2020.108182
Corentin Pigot , Guillaume Noirbent , Sébastien Peralta , Sylvain Duval , Thanh-Tuan Bui , Pierre-Henri Aubert , Malek Nechab , Didier Gigmes , Frédéric Dumur

A series of twelve dyes have been designed using 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)malononitrile as the electron acceptor. While using piperidine as a classical base for the Knoevenagel reaction, a nucleophilic attack of the amine on the formed push-pull chromophore occurred, producing an azafluorenone derivative. By varying the amine, a series of azafluorenones could be obtained. By using an aldehyde of extended conjugation, a spontaneous aromatization following the cyclization reaction could also be demonstrated. The optical, electrochemical properties of the different dyes were examined. Theoretical calculations were also carried out to support the experimental results.



中文翻译:

基于2-(3-氧代-2,3-二氢-1 H-环戊[ b ]萘-1-亚烷基)丙二腈的新型推挽染料:一种胺定向合成

使用2-(3-氧代-2,3-二氢-1 H-环戊[ b ]萘-1-亚烷基)丙二腈作为电子受体设计了一系列十二种染料。当使用哌啶作为Knoevenagel反应的经典碱时,发生了胺对形成的推挽生色团的亲核攻击,产生了氮杂芴酮衍生物。通过改变胺,可以获得一系列的氮杂芴酮。通过使用扩展共轭的醛,还可以证明环化反应后的自发芳构化。检查了不同染料的光学,电化学性质。还进行了理论计算以支持实验结果。

更新日期:2020-01-07
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