Structural Engineering of Luminogens with High Emission Efficiency Both in Solution and in the Solid State

Developing molecules with high emission efficiency both in solution and the solid state is still a great challenge, since most organic luminogens are either aggregation‐caused quenching or aggregation‐induced emission molecules. This dilemma was overcome by integrating planar and distorted structure...

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Veröffentlicht in:Angewandte Chemie International Edition 2019-08, Vol.58 (33), p.11419-11423
Hauptverfasser: Wu, Hongwei, Chen, Zhao, Chi, Weijie, Bindra, Anivind Kaur, Gu, Long, Qian, Cheng, Wu, Bing, Yue, Bingbing, Liu, Guofeng, Yang, Guangbao, Zhu, Liangliang, Zhao, Yanli
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container_end_page 11423
container_issue 33
container_start_page 11419
container_title Angewandte Chemie International Edition
container_volume 58
creator Wu, Hongwei
Chen, Zhao
Chi, Weijie
Bindra, Anivind Kaur
Gu, Long
Qian, Cheng
Wu, Bing
Yue, Bingbing
Liu, Guofeng
Yang, Guangbao
Zhu, Liangliang
Zhao, Yanli
description Developing molecules with high emission efficiency both in solution and the solid state is still a great challenge, since most organic luminogens are either aggregation‐caused quenching or aggregation‐induced emission molecules. This dilemma was overcome by integrating planar and distorted structures with long alkyl side chains to achieve DAπAD type emitters. A linear diphenyl–diacetylene core and the charge transfer effect ensure considerable planarity of these molecules in the excited state, allowing strong emission in dilute solution (quantum yield up to 98.2 %). On the other hand, intermolecular interactions of two distorted cyanostilbene units restrict molecular vibration and rotation, and long alkyl chains reduce the quenching effect of the π–π stacking to the excimer, eventually leading to strong emission in the solid state (quantum yield up to 60.7 %). The integration of planar and distorted structures with long alkyl side chains to obtain molecules with high emission efficiency both in solution and the solid state is demonstrated. Efficient intracellular bioimaging using the molecules with different concentrations demonstrates the possibility of applying the highly emissive systems.
doi_str_mv 10.1002/anie.201906507
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This dilemma was overcome by integrating planar and distorted structures with long alkyl side chains to achieve DAπAD type emitters. A linear diphenyl–diacetylene core and the charge transfer effect ensure considerable planarity of these molecules in the excited state, allowing strong emission in dilute solution (quantum yield up to 98.2 %). On the other hand, intermolecular interactions of two distorted cyanostilbene units restrict molecular vibration and rotation, and long alkyl chains reduce the quenching effect of the π–π stacking to the excimer, eventually leading to strong emission in the solid state (quantum yield up to 60.7 %). The integration of planar and distorted structures with long alkyl side chains to obtain molecules with high emission efficiency both in solution and the solid state is demonstrated. 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subjects Agglomeration
bioimaging
Chains
Charge transfer
Emission
Emitters
Excimers
luminescence
molecular engineering
molecular stacking
noncovalent interactions
Quenching
Solid state
Structural engineering
Vibration
title Structural Engineering of Luminogens with High Emission Efficiency Both in Solution and in the Solid State
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