CONSECUTIVE THREE-COMPONENT SYNTHESIS OF FILM LUMINESCENT INDOLONE MEROCYANINES WITH L-AMINO ACID ESTER DONORS

Authors

  • C. Muschelknautz Heinrich-Heine-Universität Düsseldorf, Institut für Organische Chemie und Makromolekulare Chemie
  • B. Mayer Heinrich-Heine-Universität Düsseldorf, Institut für Organische Chemie und Makromolekulare Chemie
  • F. Rominger Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg
  • T. J. J. Müller Heinrich-Heine-Universität Düsseldorf, Institut für Organische Chemie und Makromolekulare Chemie

DOI:

https://doi.org/10.1007/433

Keywords:

alkynes, amino acids, computations, cyclocarbopalladation, fluorescence, multicomponent reactions, indolones, insertion, Sonogashira coupling

Abstract

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 dropcasted films of all representatives display pronounced aggregation-induced orange-red fluorescence with large Stokes shifts, while all chromophores are nonemissive in solution.

Also published in Chemistry of Heterocyclic Compounds, 2013, 49 (6), pp 860-871

http://link.springer.com/article/10.1007/s10593-013-1320-3

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Published

2013-06-13

Issue

No. 6 (2013)

Section

Original Papers