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Consecutive three-component synthesis of film luminescent indolone merocyanines with L-amino acid ester donors

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Chemistry of Heterocyclic Compounds Aims and scope

Prop-2-enylidene indolones substituted with L-amino acid esters are obtained in good to excellent yields in a consecutive three-component cyclocarbopalladation, Sonogashira coupling, and Michael addition sequence. While primary L-amino acid esters furnish a mixture of E,E- and E,Z-configurated diastereomers, L-proline methyl ester selectively and exclusively furnishes the E,E-isomer. As already discovered for other 3-aminoprop-2-enylidene indolones, the drop-casted films of all representatives display pronounced aggregation-induced orange-red fluorescence with large Stokes shifts, while all chromophores are nonemissive in solution.

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Authors and Affiliations

  1. Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, D-40225, Düsseldorf, Germany

    C. Muschelknautz, B. Mayer & T. J. J. Müller

  2. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, D-69120, Heidelberg, Germany

    F. Rominger

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  1. C. Muschelknautz
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  2. B. Mayer
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  3. F. Rominger
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  4. T. J. J. Müller
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Correspondence to T. J. J. Müller.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 922–934, June, 2013.

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Muschelknautz, C., Mayer, B., Rominger, F. et al. Consecutive three-component synthesis of film luminescent indolone merocyanines with L-amino acid ester donors. Chem Heterocycl Comp 49, 860–871 (2013). https://doi.org/10.1007/s10593-013-1320-3

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