Solid-State Emissive Triarylborane-Based [2.2]Paracyclophanes Displaying Circularly Polarized Luminescence and Thermally Activated Delayed Fluorescence

被引:84
作者
Zhang, Meng-Yuan [1 ]
Li, Zhi-Yi [2 ]
Lu, Bo [1 ]
Wang, Ying [2 ]
Ma, Yu-Dao [1 ]
Zhao, Cui-Hua [1 ]
机构
[1] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China
[2] Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
基金
中国国家自然科学基金;
关键词
LIGHT-EMITTING-DIODES; SPACE CHARGE-TRANSFER; PI-ELECTRON SYSTEMS; OPTICAL-PROPERTIES; ORGANIC-SOLIDS; ELECTROLUMINESCENCE; MOLECULES; BORON; DELOCALIZATION; ASSEMBLIES;
D O I
10.1021/acs.orglett.8b02995
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New types of [2.2]paracyclophane derivatives, g-BNMe2-Cp and mBNMe(2)-Cp, in which electron-donating NMe2 and the electron-accepting BMes(2) are introduced at the pseudo-gem and pseudo-meta positions, were designed and synthesized. The efficient through-space charge transfer enables the intense fluorescence with thermally activated delayed fluorescence characteristics. The quantum yields are up to 0.72 and 0.39 in cyclohexane. In addition, no significant fluorescence quenching was observed in the solid state with fluorescence quantum yields of powder up to 0.53 and 0.33. Moreover, the enantiomerically pure forms of g-BNMe2-Cp exhibit strong CPL signals with g(lum) up to 4.24 X 10(-3).
引用
收藏
页码:6868 / 6871
页数:4
相关论文
共 48 条
[1]   Solid-state circularly polarised luminescence of atropisomeric fluorophores embedded in achiral myo-inositol-containing polyurethanes [J].
Amako, Tomoyuki ;
Nakabayashi, Kazuki ;
Sudo, Atsushi ;
Fujiki, Michiya ;
Imai, Yoshitane .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (10) :2913-2917
[2]   Three-dimensional nonlinear optical chromophores based on through-space delocalization [J].
Bartholomew, GP ;
Ledoux, I ;
Mukamel, S ;
Bazan, GC ;
Zyss, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13480-13485
[3]   Lanthanide complexes as chiral probes exploiting circularly polarized luminescence [J].
Carr, Rachel ;
Evans, Nicholas H. ;
Parker, David .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (23) :7673-7686
[4]   Solid-State Emissive B,S-Bridged p-Terphenyls: Synthesis, Properties, and Utility as Bifunctional Fluorescent Sensor for Hg2+ and F- Ions [J].
Chen, Dong-Mei ;
Wang, Sheng ;
Li, Hong-Xiang ;
Zhu, Xiao-Zhang ;
Zhao, Cui-Hua .
INORGANIC CHEMISTRY, 2014, 53 (23) :12532-12539
[5]   Design and synthesis of planar chiral heterocyclic carbene precursors derived from [2.2]paracyclophane [J].
Duan, Wenzeng ;
Ma, Yudao ;
Xia, Houqi ;
Liu, Xueying ;
Ma, Qingshuang ;
Sun, Junshan .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (11) :4330-4333
[6]  
Entwistle CD, 2002, ANGEW CHEM INT EDIT, V41, P2927, DOI 10.1002/1521-3773(20020816)41:16<2927::AID-ANIE2927>3.0.CO
[7]  
2-L
[8]   Design and Synthesis of New Circularly Polarized Thermally Activated Delayed Fluorescence Emitters [J].
Feuillastre, Sophie ;
Pauton, Mathilde ;
Gao, Longhui ;
Desmarchelier, Alaric ;
Riives, Adrian J. ;
Prim, Damien ;
Tondelier, Denis ;
Geffroy, Bernard ;
Muller, Gilles ;
Clavier, Gilles ;
Pieters, Gregory .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (12) :3990-3993
[9]   p-Quaterphenyls Laterally Substituted with a Dimesitylboryl Group: A Promising Class of Solid-State Blue Emitters [J].
Fu, Guang-Liang ;
Zhang, Hong-Yu ;
Yan, Yi-Qiao ;
Zhao, Cui-Hua .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (04) :1983-1990
[10]   A silver(I)-induced higher-ordered structure based on planar chiral tetrasubstituted [2.2]paracyclophane [J].
Gon, Masayuki ;
Morisaki, Yasuhiro ;
Chujo, Yoshiki .
CHEMICAL COMMUNICATIONS, 2017, 53 (59) :8304-8307