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Photophysics of 9,9-Dimethylacridan-Substituted Phenylstyrylpyrimidines Exhibiting Long-Lived Intramolecular Charge-Transfer Fluorescence and Aggregation-Induced Emission Characteristics
Authors: Fecková Michaela | Kalis Ioannis Konstantinos | Roisnel Thierry | le Poul Pascal | Pytela Oldřich | Klikar Milan | Robin-le Guen Francoise | Bureš Filip | Fakis Mihalis | Achelle Sylvain
Year: 2021
Type of publication: článek v odborném periodiku
Name of source: Chemistry - A European Journal
Publisher name: Wiley-VCH
Place: Weinheim
Page from-to: 1145–1159
Titles:
Language Name Abstract Keywords
cze Fotofyzikální vlastnosti 9,9-dimethylakridanem substituovaných fenylstyrylpyrimidinů – charakteristiky dlouhotrvající intramolekulární charge-transfer fluorescence a agregací indukované emise Cross-couplingovými reakcemi a Knoevenagelovou kondenzací bylo připraveno šest push-pull molekul na bázi pyrimidinu substituovaných v polohách C2 a C4/6 fenylakridanem a styrenovými fragmenty, dekorované methoxy nebo N,N-difenylamino substituenty jako donory. X-ray analýzy potvrdily strukturu látek, akridanová část je orientována kolmo ke zbývajícími pi-systému. Fotofyzikální studie potvrdily významné rozdíly mezi methoxy s N,N-difenylamino chromofory. Při solvatochromních studiích vykazovaly methoxy deriváty duální emisi v polárních rozpouštědlech. emise indukovaná agregací; donor-akceptorový systém; duální emise; přenos náboje; fluorescence
eng Photophysics of 9,9-Dimethylacridan-Substituted Phenylstyrylpyrimidines Exhibiting Long-Lived Intramolecular Charge-Transfer Fluorescence and Aggregation-Induced Emission Characteristics Six pyrimidine-based push-pull systems substituted at positions C2 and C4/6 with phenylacridan and styryl moieties, employing methoxy or N,N-diphenylamino donors, have been designed and synthesized through cross-coupling and Knoevenagel reactions. X-ray analysis confirmed that the molecular structure featured the acridan moiety arranged perpendicularly to the residual pi system. Photophysical studies revealed significant differences between the methoxy and N,N-diphenylamino chromophores. Solvatochromic studies revealed that the methoxy derivatives showed dual emission in polar solvents. Time-resolved spectroscopy revealed that the higher energy band involved very fast (<80 ps) fluorescence, whereas the lower energy one included long components (approximate to 30 ns) due to long-lived intramolecular charge-transfer fluorescence. In contrast to N,N-diphenylamino chromophores, the methoxy derivatives also showed aggregation-induced emission in mixtures of THF/water, as well as dual emission in thin films, covering almost the whole visible spectrum with corresponding chromaticity coordinates not far from that of pure white light. These properties render the methoxy derivatives as very promising organic materials for white organic light-emitting diodes. aggregation-induced emission; donor– acceptor systems; dual emission; charge transfer; fluorescence

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