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Triskelion‐Shaped π‐Luminophores Bearing Coumarin: Syntheses, Structures, and Luminescence Properties
ChemPhotoChem ( IF 3.0 ) Pub Date : 2020-06-03 , DOI: 10.1002/cptc.202000049 Masafumi Ueda 1 , Mirai Kokubun 1 , Yasuhiro Mazaki 1
ChemPhotoChem ( IF 3.0 ) Pub Date : 2020-06-03 , DOI: 10.1002/cptc.202000049 Masafumi Ueda 1 , Mirai Kokubun 1 , Yasuhiro Mazaki 1
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Triskelion‐shaped π‐luminophores bearing three coumarin units 1 a and 1 b were successfully synthesized by the intramolecular Ullmann coupling reaction of triphenyl benzene‐1,3,5‐tricarboxylate derivatives. X‐ray crystal structure analysis revealed that compound 1 adopts a unique curved and three‐blade propeller‐shaped structure. These crystals are a racemic mixture consisting of PPP‐ and MMM‐1 due to the helicity resulting from the steric hindrance. A computational study suggests that this helical inversion process between PPP‐ and MMM‐1 a occurs with comparative ease. The emission spectra of 1 a and 1 b in THF solution showed sharp emission bands at 454 nm and 492 nm, respectively. The Stokes shifts were relatively large at 7385 cm−1 and 6556 cm−1 due to their degenerate frontier molecular orbitals. A solution of 1 b in different organic solvents demonstrated solvatofluorochromism due to intramolecular charge transfer of the coumarin unit in the excited states. Interestingly, both triskelion‐shaped molecules formed aggregates in a mixture of THF‐H2O and exhibited aggregation‐induced emission enhancement characteristics.
中文翻译：
带有香豆素的Triskelion形π发光体：合成，结构和发光特性
通过三苯基苯-1,3,5-三羧酸酯衍生物的分子内Ullmann偶联反应成功合成了带有三个香豆素单元1a和1b的Triskelion形π发光体。X射线晶体结构分析表明，化合物1采用独特的弯曲和三叶螺旋桨形结构。这些晶体是由PPP-和MMM - 1组成的外消旋混合物，这是由于空间位阻引起的螺旋。一项计算研究表明，PPP-和MMM - 1a之间的这种螺旋反演过程比较容易发生。的发射光谱THF溶液中的1a和1b分别在454 nm和492 nm处显示出清晰的发射带。由于斯托克斯位移的简并前沿分子轨道，它们在7385 cm -1和6556 cm -1处相对较大。的溶液1b中在不同的有机溶剂表现出solvatofluorochromism由于激发态的香豆素单元的分子内电荷转移。有趣的是，两个三方形的分子在THF-H 2 O的混合物中形成聚集体，并表现出聚集体诱导的发射增强特性。
更新日期：2020-06-03
中文翻译：
带有香豆素的Triskelion形π发光体：合成，结构和发光特性
通过三苯基苯-1,3,5-三羧酸酯衍生物的分子内Ullmann偶联反应成功合成了带有三个香豆素单元1a和1b的Triskelion形π发光体。X射线晶体结构分析表明，化合物1采用独特的弯曲和三叶螺旋桨形结构。这些晶体是由PPP-和MMM - 1组成的外消旋混合物，这是由于空间位阻引起的螺旋。一项计算研究表明，PPP-和MMM - 1a之间的这种螺旋反演过程比较容易发生。的发射光谱THF溶液中的1a和1b分别在454 nm和492 nm处显示出清晰的发射带。由于斯托克斯位移的简并前沿分子轨道，它们在7385 cm -1和6556 cm -1处相对较大。的溶液1b中在不同的有机溶剂表现出solvatofluorochromism由于激发态的香豆素单元的分子内电荷转移。有趣的是，两个三方形的分子在THF-H 2 O的混合物中形成聚集体，并表现出聚集体诱导的发射增强特性。
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