Three‐Component Activation/Alkynylation/Cyclocondensation (AACC) Synthesis of Enhanced Emission Solvatochromic 3‐Ethynylquinoxalines

Three‐Component Activation/Alkynylation/Cyclocondensation (AACC) Synthesis of Enhanced Emission... 2‐Substituted 3‐ethynylquinoxaline chromophores can be readily synthesized by a consecutive activation–alkynylation–cyclocondensation (AACC) one‐pot sequence in a three‐component manner. In comparison with the previously published four‐component glyoxylation starting from electron‐rich π‐nucleophiles, the direct activation of (hetero)aryl glyoxylic acids allows the introduction of substituents that cannot be directly accessed by glyoxylation. By introducing N,N‐dimethylaniline as a strong donor in the 2‐position, the emission solvatochromicity of 3‐ethynylquinoxalines can be considerably enhanced to cover the spectral range from blue–green to deep red–orange with a single chromophore in a relatively narrow polarity window. The diversity‐oriented nature of the synthetic multicomponent reaction concept enables comprehensive investigations of structure–property relationships by Hammett correlations and Lippert–Mataga analysis, as well as the elucidation of the electronic structure of the emission solvatochromic π‐conjugated donor–acceptor systems by DFT and time‐dependent DFT calculations with the PBEh1PBE functional for a better reproduction of the dominant charge‐transfer character of the longest wavelength absorption band. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemistry - A European Journal Wiley

Three‐Component Activation/Alkynylation/Cyclocondensation (AACC) Synthesis of Enhanced Emission Solvatochromic 3‐Ethynylquinoxalines

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Publisher
Wiley
Copyright
© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
0947-6539
eISSN
1521-3765
D.O.I.
10.1002/chem.201800079
Publisher site
See Article on Publisher Site

Abstract

2‐Substituted 3‐ethynylquinoxaline chromophores can be readily synthesized by a consecutive activation–alkynylation–cyclocondensation (AACC) one‐pot sequence in a three‐component manner. In comparison with the previously published four‐component glyoxylation starting from electron‐rich π‐nucleophiles, the direct activation of (hetero)aryl glyoxylic acids allows the introduction of substituents that cannot be directly accessed by glyoxylation. By introducing N,N‐dimethylaniline as a strong donor in the 2‐position, the emission solvatochromicity of 3‐ethynylquinoxalines can be considerably enhanced to cover the spectral range from blue–green to deep red–orange with a single chromophore in a relatively narrow polarity window. The diversity‐oriented nature of the synthetic multicomponent reaction concept enables comprehensive investigations of structure–property relationships by Hammett correlations and Lippert–Mataga analysis, as well as the elucidation of the electronic structure of the emission solvatochromic π‐conjugated donor–acceptor systems by DFT and time‐dependent DFT calculations with the PBEh1PBE functional for a better reproduction of the dominant charge‐transfer character of the longest wavelength absorption band.

Journal

Chemistry - A European JournalWiley

Published: Jan 7, 2018

Keywords: ; ; ; ;

References

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