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Pyrene‐fused Dibenzoazatetracenes: Synthesis, Crystal Structures, Photophysical Properties and their Morphologies
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2020-12-02 , DOI: 10.1002/ajoc.202000616 Qingsong Wang 1 , Wei Gao 1 , Yan Chen 1 , Xiaohui Wang 1 , Jin Zeng 1 , Yiwei Liu 1 , Huijuan Ran 2 , Zhen Hu 1 , Jie Bai 1 , Xing Feng 1 , Carl Redshaw 3 , Qing Chen 4 , Jian‐Yong Hu 2
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2020-12-02 , DOI: 10.1002/ajoc.202000616 Qingsong Wang 1 , Wei Gao 1 , Yan Chen 1 , Xiaohui Wang 1 , Jin Zeng 1 , Yiwei Liu 1 , Huijuan Ran 2 , Zhen Hu 1 , Jie Bai 1 , Xing Feng 1 , Carl Redshaw 3 , Qing Chen 4 , Jian‐Yong Hu 2
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Molecular packing and microstructure can play a crucial role in the photophysical and electronic properties of organic semiconductor materials. This article presents six pyrene‐fused dibenzoazatetracenes 3 and the relationship between their molecular structures and the emission, and as well as the morphology has been investigated. All of the compounds display an aggregation‐caused emission quenching effect due to the extended π‐conjugation associated with the close π‐π stacking in their crystal structures. In terms of fluorescence, the compounds emitted sky‐blue emission with a maximum peak (λmaxem) in the range 469–474 nm with a quantum yield (Φf) of 0.37–0.50 in solution. In the solid state, the emission maximum red‐shifts to ∼528 nm and possesses a relatively low quantum yield (<0.16). In addition, the electronic effects of the terminal group shows only a limited effect on the emission behavior. On the other hand, tert‐butyl groups have been introduced at the pyrene core, and contribute to enhance the solubility of the compound, and also improve the quality of the morphology.
中文翻译：
fused稠合的二苯并氮杂卓烷酮：合成，晶体结构，光物理性质及其形态
分子堆积和微结构可以在有机半导体材料的光物理和电子特性中发挥关键作用。本文介绍了六个pyr稠合的二苯并azatetracenes 3及其分子结构与发射之间的关系，并研究了其形态。由于与它们的晶体结构中紧密的π-π堆积有关的扩展的π-共轭作用，所有这些化合物都表现出聚集引起的发射猝灭效应。在荧光的方面，所述化合物发出的天蓝色发射具有最大峰（λ maxem）范围469-474纳米具有量子产率（Φ ˚F）在溶液中的0.37–0.50。在固态状态下，最大发射红移至〜528 nm，并且具有相对较低的量子产率（<0.16）。此外，端基的电子效应对发射行为仅显示出有限的效应。另一方面，叔丁基已引入the中心，有助于增强化合物的溶解性，并改善形态质量。
更新日期：2021-01-18
中文翻译：
fused稠合的二苯并氮杂卓烷酮：合成，晶体结构，光物理性质及其形态
分子堆积和微结构可以在有机半导体材料的光物理和电子特性中发挥关键作用。本文介绍了六个pyr稠合的二苯并azatetracenes 3及其分子结构与发射之间的关系，并研究了其形态。由于与它们的晶体结构中紧密的π-π堆积有关的扩展的π-共轭作用，所有这些化合物都表现出聚集引起的发射猝灭效应。在荧光的方面，所述化合物发出的天蓝色发射具有最大峰（λ maxem）范围469-474纳米具有量子产率（Φ ˚F）在溶液中的0.37–0.50。在固态状态下，最大发射红移至〜528 nm，并且具有相对较低的量子产率（<0.16）。此外，端基的电子效应对发射行为仅显示出有限的效应。另一方面，叔丁基已引入the中心，有助于增强化合物的溶解性，并改善形态质量。
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