Intramolecular Energy and Solvent-Dependent Chirality Transfer within a BINOL-Perylene Hetero-Cyclophane

被引：40
作者：
Ouyang, Guanghui [1 ,2 ,3 ]
Ruehe, Jessica [1 ,2 ]
Zhang, Yang [4 ]
Lin, Mei-Jin [4 ]
Liu, Minghua [3 ]
Wuerthner, Frank [1 ,2 ]
机构：
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[2] Univ Wurzburg, Ctr Nanosyst Chem, D-97074 Wurzburg, Germany
[3] Chinese Acad Sci, CAS Key Lab Colloid Interface & Chem Thermodynam, Inst Chem, North First St 2, Beijing 100190, Peoples R China
[4] Fuzhou Univ, Coll Chem, State Key Lab Photocatalysis Energy & Environm, Fuzhou 350116, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 31期
关键词：
Chirality Transfer; Cyclophanes; Energy Transfer; Perylene Bisimide; Solvent Effects; BISIMIDE CYCLOPHANE; GUEST; HOST; RESOLUTION; COMPLEXES; DYES;
D O I：
10.1002/anie.202206706
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Multichromophoric macrocycles and cyclophanes are important supramolecular architectures for the elucidation of interchromophoric interactions originating from precise spatial organization. Herein, by combining an axially chiral binaphthol bisimide (BBI) and a bay-substituted conformationally labile twisted perylene bisimide (PBI) within a cyclophane of well-defined geometry, we report a chiral PBI hetero-cyclophane (BBI-PBI) that shows intramolecular energy and solvent-regulated chirality transfer from the BBI to the PBI subunit. Excellent spectral overlap and spatial arrangement of BBI and PBI lead to efficient excitation energy transfer and subsequent PBI emission with high quantum yield (80-98 %) in various solvents. In contrast, chirality transfer is strongly dependent on the respective solvent as revealed by circular dichroism (CD) spectroscopy. The combination of energy and chirality transfer affords a bright red circularly polarized luminescence (CPL) from the PBI chromophore by excitation of BBI.
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页数：5
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