New push-pull dyes based on 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)malononitrile: An amine-directed synthesis - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Dyes and Pigments Année : 2020

New push-pull dyes based on 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)malononitrile: An amine-directed synthesis

Résumé

A series of twelve dyes have been designed using 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-yli-dene)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 azaflu-orenone 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.

Domaines

Matériaux
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Dates et versions

hal-02866910 , version 1 (02-07-2020)

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Corentin Pigot, Guillaume Noirbent, Sebastien Peralta, Sylvain Duval, Thanh-Tuan Bui, et al.. 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, 2020, 175, pp.108182. ⟨10.1016/j.dyepig.2020.108182⟩. ⟨hal-02866910⟩
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