Three-Component Activation/Alkynylation/Cyclocondensation (AACC) Synthesis of Enhanced Emission Solvatochromic 3-Ethynylquinoxalines
| Autor: | Irina Gruber, Christoph Janiak, Simon P. Höwedes, Charlotte F. Gers-Panther, Thomas Müller, Franziska K. Merkt |
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| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Chemistry Component (thermodynamics) Polarity (physics) Aryl Solvatochromism Organic Chemistry Electronic structure General Chemistry Chromophore 010402 general chemistry 01 natural sciences Fluorescence Catalysis 0104 chemical sciences chemistry.chemical_compound Alkynylation Computational chemistry |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 24(32) |
| ISSN: | 1521-3765 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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