Organic Room‐Temperature Phosphorescence with Strong Circularly Polarized Luminescence Based on Paracyclophanes

• Published in: Angewandte Chemie International Edition Vol. 58; no. 48; pp. 17220 - 17225
• Main Authors: Liang, Xiao, Liu, Ting‐Ting, Yan, Zhi‐Ping, Zhou, Yan, Su, Jian, Luo, Xu‐Feng, Wu, Zheng‐Guang, Wang, Yi, Zheng, You‐Xuan, Zuo, Jing‐Lin
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 25.11.2019; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Bromine; Charge transfer; Chemistry; Chemistry, Multidisciplinary; Circular polarization; dissymmetry factor; Enantiomers; Luminescence; Organic materials; organic room-temperature phosphorescence; paracyclophane; Phosphorescence; Physical Sciences; Science & Technology; Space charge; Temperature; Toluene; paracyclophane; dissymmetry factor; luminescence; organic room-temperature phosphorescence; FLUORESCENCE; circular polarization
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201909076

Pure organic materials with intrinsic room‐temperature phosphorescence typically rely on heavy atoms or heteroatoms. Two different strategies towards constructing organic room‐temperature phosphorescence (RTP) species based upon the through‐space charge transfer (TSCT) unit of [2.2]paracyclophane (PCP) were demonstrated. Materials with bromine atoms, PCP‐BrCz and PPCP‐BrCz, exhibit RTP lifetime of around 100 ms. Modulating the PCP core with non‐halogen‐containing electron‐withdrawing units, PCP‐TNTCz and PCP‐PyCNCz, successfully elongate the RTP lifetime to 313.59 and 528.00 ms, respectively, the afterglow of which is visible for several seconds under ambient conditions. The PCP‐TNTCz and PCP‐PyCNCz enantiomers display excellent circular polarized luminescence with dissymmetry factors as high as −1.2×10−2 in toluene solutions, and decent RTP lifetime of around 300 ms for PCP‐TNTCz enantiomers in crystalline state. A series of organic phosphors based on paracyclophanes (PCPs) exhibit both strong room‐temperature phosphorescence (RTP) and excellent circularly polarized luminescence. Modulating the PCP core with non‐halogen‐containing electron‐withdrawing units elongates the RTP lifetime to 313.59 and 528.00 ms. The afterglow is visible for several seconds under ambient conditions.