Cyclodextrins with Multiple Pyrenyl Groups: An Approach to Organic Molecules Exhibiting Bright Excimer Circularly Polarized Luminescence
Cyclodextrins with Multiple Pyrenyl Groups: An Approach to Organic Molecules Exhibiting Bright Excimer Circularly Polarized Luminescence
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DOI：
10.1002/anie.202114700
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发表时间：
2021-12-29
影响因子：
16.6
通讯作者：
Kida, Toshiyuki
中科院分区：
文献类型：
--
作者：
Shigemitsu, Hajime;Kawakami, Kosei;Kida, Toshiyuki
我们报道了一种简单有效的方法，有机分子表现出明亮的圆偏振发光（CPL）相结合的手性环状分子支架和多个准分子使能部分。用六个芘基修饰α-环糊精（CyD）支架，以从市售化合物一步合成得到芘-环糊精（PCD）。PCD具有高的摩尔消光系数（λ = 10（5）M-1 cm（-1）），偏振发射具有良好的不对称因子（|g（lum）|近似10（-2））和量子产率（φ（f）近似0.5）。由于PCD具有良好的物理化学性能，其圆偏振发光亮度（B-CPL）达到340 M-1 cm（-1）。光物理和手性研究的PCD只有5个芘单元和连接的CyD与芘单元的各种长度的连接器显示，在空间拥挤的环境中形成的芘准分子是至关重要的CPL各向异性。该研究为开发具有良好发光性能的CPL有机分子奠定了基础。
We report a simple and effective approach to organic molecules exhibiting bright circularly polarized luminescence (CPL) by combining a chiral cyclic molecular scaffold and multiple excimer-enabling moieties. An alpha-cyclodextrin (CyD) scaffold was modified with six pyrenyl groups to obtain pyrene-cyclodextrins (PCDs) in a one-step synthesis from commercially available compounds. The PCDs exhibited high molar extinction coefficients (epsilon approximate to 10(5) M-1 cm(-1)), polarized emission with a good dissymmetry factor (|g(lum)|approximate to 10(-2)), and quantum yield (phi(f)approximate to 0.5). Owing to the excellent photophysical properties of the PCDs, the circularly polarized luminescence brightness (B-CPL) reached 340 M-1 cm(-1). Photophysical and chiroptical studies of the PCDs with only five pyrene units and with linkers of various lengths connecting the CyD with the pyrene units revealed that the formation of a pyrene excimer in a spatially crowded environment is crucial for CPL anisotropy. This study paves the way for the development of bright CPL organic molecules.