Improving the Overall Properties of Circularly Polarized Luminescent Materials Through Arene–Perfluoroarene Interactions

• Published in: Angewandte Chemie International Edition Vol. 60; no. 9; pp. 4575 - 4580
• Main Authors: Zhang, Haowen, Han, Jianlei, Jin, Xue, Duan, Pengfei
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 23.02.2021; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Anthracene; arene–perfluoroarene interactions; Assemblies; Chemistry; Chemistry, Multidisciplinary; Chirality; Circular polarization; circularly polarized luminescence; Fluorescence; Luminescence; Organic materials; Physical Sciences; Polycyclic aromatic hydrocarbons; Pyrene; Science & Technology; self-assembly; SUBSTITUTION; chirality; COCRYSTALLIZATION; RECOGNITION; perfluoroarene interactions; COMPLEXES; circularly polarized luminescence; ELECTROLUMINESCENCE; MOLECULES; arene– self-assembly; COMPETITION; CHARGE-TRANSFER INTERACTIONS; CPL; arene-perfluoroarene interactions
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202014891

A major trade‐off in the field of circularly polarized luminescence (CPL) of pure organic materials is that the large luminescence dissymmetry factor (glum) usually gives rise to the suppression of luminescence efficiency (ΦPL). Here, a supramolecular self‐assembled system, driven by arene–perfluoroarene (AP) interactions of chiral polycyclic aromatic hydrocarbons (PAHs) and octafluoronaphthalene (OFN), is reported to provide a solution to this problem. Two kinds of chiral PAHs based on pyrene and anthracene could co‐assemble with OFN in hybrid solvents to form long‐range‐ordered AP assemblies. The detailed process of AP interaction driving self‐assembly was verified by morphological measurements and fluorescence spectra. The AP assemblies exhibited chirality amplification not only in the excited state but also in the ground state. In addition, the AP assemblies showed an enhanced luminescence efficiency compared with the individual chiral PAHs due to the energy‐barrier effect of OFN. The present strategy based on AP interactions could be applied to boost the development of highly efficient CPL‐active materials. Chiral supramolecular self‐assembly driven by arene–perfluoroarene (AP) interactions are demonstrated in chiral polyaromatic hydrocarbons and octafluoronaphthalene. They exhibit a large figure of merit for boosting circularly polarized luminescence. The AP interaction amplifies both ground‐state and excited‐state chirality. Due to the high energy barrier of octafluoronaphthalene, the photoluminescence quantum efficiency of the AP complex could be significantly enhanced.