Flexible Alkylene Bridges as a Tool To Engineer Crystal Distyrylbenzene Structures Enabling Highly Fluorescent Monomeric Emission |
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Authors: | Yoshimichi Shimomura Prof. Dr. Kazunobu Igawa Dr. Shunsuke Sasaki Dr. Noritaka Sakakibara Prof. Dr. Raita Goseki Prof. Dr. Gen-ichi Konishi |
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Affiliation: | 1. Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, 152-8552 Tokyo, Japan;2. Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga 816-8580 Fukuoka, Japan;3. Université de Nantes, CNRS, Institut des Matériaux Jean Rouxel, IMN, F-44000 Nantes, France;4. Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, 152-8552 Tokyo, Japan;5. Department of Applied Chemistry, Kogakuin University, Nakano-machi, Hachioji-shi, 192-0015 Tokyo, Japan |
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Abstract: | To design ultrabright fluorescent solid dyes, a crystal engineering strategy that enables monomeric emission by blocking intermolecular electronic interactions is required. We introduced propylene moieties to distyrylbenzene (DSB) as bridges between the phenyl rings either side of its C=C bonds. The bridged DSB derivatives formed compact crystals that emit colors similar to those of the same molecules in dilute solution, with high quantum yields. The introduction of flexible seven-membered rings to the DSB core produced moderate distortion and steric hindrance in the DSB π-plane. However, owing to this strategy, it was possible to control the molecular arrangement with almost no decrease in the crystal density, and intermolecular electronic interactions were suppressed. The bridged DSB crystal structure differs from other DSB derivative structures; thus, bridging affords access to novel crystalline systems. This design strategy has important implications in many fields and is more effective than the conventional photofunctional molecular crystal design strategies. |
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Keywords: | aggregation-induced emission crystal engineering distyrylbenzene organic light-emitting devices (OLEDs) solid state fluorescence |
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