Crystallization and Aggregation-Induced Emission in a Series of Pyrrolidinylvinylquinoxaline Derivatives
| Autor: | Charlotte F. Gers-Panther, Walter Frank, Katrin Hoffmann, Ute Resch-Genger, Nithiya Nirmalananthan, Thomas Müller, Daniel Kage, Thomas Behnke |
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| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Substituent 010402 general chemistry Photochemistry 01 natural sciences Fluorescence 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials law.invention chemistry.chemical_compound General Energy Quinoxaline chemistry law Moiety Molecule Polystyrene Physical and Theoretical Chemistry Crystallization Spectroscopy |
| Zdroj: | The Journal of Physical Chemistry C. 122:11119-11127 |
| ISSN: | 1932-7455 1932-7447 |
| DOI: | 10.1021/acs.jpcc.8b01425 |
| Popis: | Aggregation-induced emission (AIE) has been meanwhile observed for many dye classes and particularly for fluorophores containing propeller-like groups. Herein, we report on the AIE characteristics of a series of four hydrophobic pyrrolidinylvinylquinoxaline (PVQ) derivatives with phenyl, pyrrolyl, indolyl, and methoxythienyl substituents used to systematically vary the torsion angle between this substituent at the quinoxaline C2 position and the planar PVQ moiety. These molecules, which are accessible via four- or five-component one-pot syntheses, were spectroscopically studied in organic solvents and solvent–water mixtures, as dye aggregates, solids, and entrapped in polystyrene particles (PSP). Steady-state and time-resolved fluorescence measurements revealed a strong fluorescence enhancement for all dyes in ethanol–water mixtures of high water content, accompanying the formation of dye aggregates with sizes of a few hundred nm, overcoming polarity and H-bonding-induced fluorescence quenching of the cha... |
| Databáze: | OpenAIRE |
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