Multiply Twisted Chiral Macrocycles Clamped by Tethered Binaphthyls Exhibiting High Circularly Polarized Luminescence Brightness

Multiply Twisted Chiral Macrocycles Clamped by Tethered Binaphthyls Exhibiting High Circularly Polarized Luminescence Brightness
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由束缚联萘钳位的多重扭曲手性大环化合物表现出高圆偏振发光亮度

DOI:
10.1002/chem.202202218
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发表时间:
2022
期刊:
Chemistry - A European Journal
影响因子:
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通讯作者:
Mazaki Yasuhiro
Mazaki Yasuhiro
中科院分区:
--
文献类型:
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作者:
Hasegawa Masashi;Hasegawa Chika;Nagaya Yuki;Tsubaki Kazunori;Mazaki Yasuhiro

文献摘要

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合成了由对苯撑和栓联联萘组成的手性大环二聚体、三聚体和四聚体,研究了它们的分子结构和手性光学性质。X射线分析和理论计算表明,多个扭曲的分子结构-二聚体,三聚体和四聚体-分别采用8字形,莫比乌斯三角形和凹矩形结构。由于萘-亚苯基-萘骨架的π-共轭,这些同系物在其紫外-维斯吸收光谱中具有大的λ值。由于形状持久的环结构和与− OCH 2CH 2 O −的束缚,实现了高荧光量子产率和相对高的不对称因子gCPLin圆偏振发光(CPL)光谱。这导致超过100的CPL亮度(BCPL),其大于常规有机CPL染料的CPL亮度。
Chiral macrocyclic dimers, trimers, and tetramers composed of paraphenylene and tethered binaphthyl were synthesized, and their molecular structures and chiroptical properties were investigated. X‐ray analysis and theoretical calculations revealed that multiple twisted molecular structures – dimers, trimers, and tetramers – adopt figure‐of‐eight, Möbius triangle, and concave rectangle structures, respectively. These homologues have largeϵvalues in their UV‐vis absorption spectra because of the π‐conjugation of the naphthalene‐phenylene‐naphthalene frameworks. Owing to the shape‐persistent ring structure and tethering with −OCH2CH2O−, high fluorescence quantum yields and a relatively high dissymmetry factorgCPLin circularly polarized luminescence (CPL) spectra were achieved. This results in CPL brightness (BCPL) of over 100, which is greater than that of the conventional organic CPL dye.