Crystallization-Enhanced Emission and Room-Temperature Phosphorescence of Cyclic Triimidazole-Monohexyl Thiophene Derivatives

The development of organic room-temperature phosphorescent (ORTP) materials represents an active field of research due to their significant advantages with respect to their organometallic counterparts. Two cyclic triimidazole (<b>TT</b>) derivatives bearing one and three hexyl-thiophene...

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Bibliographic Details
Main Authors: Daniele Malpicci, Alessandra Forni, Elena Cariati, Riku Inoguchi, Daniele Marinotto, Daniele Maver, Federico Turco, Elena Lucenti
Format: Article
Language:English
Published: MDPI AG 2022-12-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/28/1/140
Description
Summary:The development of organic room-temperature phosphorescent (ORTP) materials represents an active field of research due to their significant advantages with respect to their organometallic counterparts. Two cyclic triimidazole (<b>TT</b>) derivatives bearing one and three hexyl-thiophene moieties, <b>TT-HThio</b> and <b>TT-(HThio)<sub>3</sub></b>, have been prepared and characterized. Both compounds display enhanced quantum yields in their crystalline form with respect to those in a solution state, revealing crystallization-enhanced emissive (CEE) behavior. Importantly, while single fluorescence is observed in solution, crystalline powders also feature dual ORTP, whose respective molecular and aggregate origins have been disclosed through X-ray diffraction analysis and DFT/TDDFT calculations. The relation between the photophysical properties of <b>TT-HThio</b> and its crystallinity degree has been confirmed by a decrease in photoluminescent quantum yield (Φ) and loss of vibronic resolution when its crystals are ground in a mortar, revealing mechanochromic behavior and confirming CEE features.
ISSN:1420-3049