Aggregation-Induced Emission and Circularly Polarized Luminescence Duality in Tetracationic Binaphthyl-Based Cyclophanes

Garci, Amine; Abid, Seifallah; David, Arthur G.; Codesal, Marcos D.; Đorđević, Luka; Young, Ryan M.; Sai, Hiroaki; Le Bras, Laura; Perrier, Aurélie; Ovalle, Marco; Brown, Paige J.; Stern, Charlotte L.; Campaña, Araceli G.; Stupp, Samuel I.; Wasielewski, Michael R.; Blanco, Victor; Stoddart, J. Fraser

doi:10.1002/anie.202208679

Aggregation-Induced Emission and Circularly Polarized Luminescence Duality in Tetracationic Binaphthyl-Based Cyclophanes

Journal Article · Fri Jul 29 00:00:00 EDT 2022 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.202208679· OSTI ID:1882762

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Northwestern Univ., Evanston, IL (United States)
Univ. of Granada (Spain)
University Burgundy Franche-Comté (France)
Paris Sciences et Lettres (PSL) University (France); Centre National de la Recherche Scientifique-Mixed Organizations (CNRS-UMR), Paris (France); Paris Cité University (France)
Northwestern Univ., Evanston, IL (United States); Northwestern Univ., Chicago, IL (United States)
Northwestern Univ., Evanston, IL (United States); Univ. of New South Wales, Sydney, NSW (Australia); Zhejiang Univ., Hangzhou (China)

Here, we report an approach to the synthesis of highly charged enantiopure cyclophanes by the insertion of axially chiral enantiomeric binaphthyl fluorophores into the constitutions of pyridinium-based macrocycles. Remarkably, these fluorescent tetracationic cyclophanes exhibit a significant AIE compared to their neutral optically active binaphthyl precursors. A combination of theoretical calculations and time-resolved spectroscopy reveal that the AIE originates from limited torsional vibrations associated with the axes of chirality present in the chiral enantiomeric binaphthyl units and the fine-tuning of their electronic landscape when incorporated within the cyclophane structure. Furthermore, these highly charged enantiopure cyclophanes display CPL responses both in solution and in the aggregated state. This unique duality of AIE and CPL in these tetracationic cyclophanes is destined to be of major importance in future development of photonic devices and bio-applications.

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Research Organization:: Northwestern Univ., Evanston, IL (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES). Scientific User Facilities (SUF)

Grant/Contract Number:: SC0000989

OSTI ID:: 1882762

Alternate ID(s):: OSTI ID: 1882765
OSTI ID: 2419551

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 40 Vol. 61; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

References (90)

Diastereoselective Self-Assembly of [2]Catenanes Ashton, Peter R.; Heiss, Aaron M.; Pasini, Dario European Journal of Organic Chemistry, Vol. 1999, Issue 5 https://doi.org/10.1002/(SICI)1099-0690(199905)1999:5<995::AID-EJOC995>3.0.CO;2-K	journal	May 1999
Manipulation of Charge and Exciton Distribution Based on Blue Aggregation-Induced Emission Fluorophors: A Novel Concept to Achieve High-Performance Hybrid White Organic Light-Emitting Diodes Liu, Baiquan; Nie, Han; Zhou, Xingbang Advanced Functional Materials, Vol. 26, Issue 5 https://doi.org/10.1002/adfm.201503368	journal	December 2015
Achieving High-Performance Nondoped OLEDs with Extremely Small Efficiency Roll-Off by Combining Aggregation-Induced Emission and Thermally Activated Delayed Fluorescence Guo, Jingjing; Li, Xiang-Long; Nie, Han Advanced Functional Materials, Vol. 27, Issue 13 https://doi.org/10.1002/adfm.201606458	journal	February 2017
Endowing Perovskite Nanocrystals with Circularly Polarized Luminescence Shi, Yonghong; Duan, Pengfei; Huo, Shengwei Advanced Materials, Vol. 30, Issue 12 https://doi.org/10.1002/adma.201705011	journal	January 2018
Aggregation‐Induced Circularly Polarized Luminescence: Chiral Organic Materials for Emerging Optical Technologies Nitti, Andrea; Pasini, Dario Advanced Materials, Vol. 32, Issue 41 https://doi.org/10.1002/adma.201908021	journal	March 2020
Aggregation‐Induced Emission Luminogens Married to 2D Black Phosphorus Nanosheets for Highly Efficient Multimodal Theranostics Huang, Jiachang; He, Benzhao; Zhang, Zhijun Advanced Materials, Vol. 32, Issue 37 https://doi.org/10.1002/adma.202003382	journal	August 2020
Furan Is Superior to Thiophene: A Furan-Cored AIEgen with Remarkable Chromism and OLED Performance Zhao, Zheng; Nie, Han; Ge, Congwu Advanced Science, Vol. 4, Issue 8 https://doi.org/10.1002/advs.201700005	journal	February 2017
Highly Efficient Far Red/Near-Infrared Solid Fluorophores: Aggregation-Induced Emission, Intramolecular Charge Transfer, Twisted Molecular Conformation, and Bioimaging Applications Lu, Hongguang; Zheng, Yadan; Zhao, Xiaowei Angewandte Chemie, Vol. 128, Issue 1 https://doi.org/10.1002/ange.201507031	journal	November 2015
Aggregation-Induced Delayed Fluorescence Based on Donor/Acceptor-Tethered Janus Carborane Triads: Unique Photophysical Properties of Nondoped OLEDs Furue, Ryuhei; Nishimoto, Takuro; Park, In Seob Angewandte Chemie, Vol. 128, Issue 25 https://doi.org/10.1002/ange.201603232	journal	May 2016
Highly Efficient Nondoped OLEDs with Negligible Efficiency Roll-Off Fabricated from Aggregation-Induced Delayed Fluorescence Luminogens Huang, Jian; Nie, Han; Zeng, Jiajie Angewandte Chemie, Vol. 129, Issue 42 https://doi.org/10.1002/ange.201706752	journal	September 2017
AIE Triggers the Circularly Polarized Luminescence of Atomically Precise Enantiomeric Copper(I) Alkynyl Clusters Zhang, Miao‐Miao; Dong, Xi‐Yan; Wang, Zhao‐Yang Angewandte Chemie, Vol. 132, Issue 25 https://doi.org/10.1002/ange.201908909	journal	September 2019
Selective Synthesis of Conjugated Chiral Macrocycles: Sidewall Segments of (−)/(+)‐(12,4) Carbon Nanotubes with Strong Circularly Polarized Luminescence Wang, Jinyi; Zhuang, Guilin; Chen, Muqing Angewandte Chemie, Vol. 132, Issue 4 https://doi.org/10.1002/ange.201909401	journal	December 2019
ACQ‐to‐AIE Transformation: Tuning Molecular Packing by Regioisomerization for Two‐Photon NIR Bioimaging Li, Yuanyuan; Liu, Shunjie; Ni, Huwei Angewandte Chemie, Vol. 132, Issue 31 https://doi.org/10.1002/ange.202005785	journal	June 2020
Aggregations‐induzierte Emission (AIE): Eine historische Betrachtung Würthner, Frank Angewandte Chemie, Vol. 132, Issue 34 https://doi.org/10.1002/ange.202007525	journal	July 2020
500‐Fold Amplification of Small Molecule Circularly Polarised Luminescence through Circularly Polarised FRET Wade, Jessica; Brandt, Jochen R.; Reger, David Angewandte Chemie, Vol. 133, Issue 1 https://doi.org/10.1002/ange.202011745	journal	December 2020
AIE‐Active Chiral [3]Rotaxanes with Switchable Circularly Polarized Luminescence Li, Wei‐Jian; Gu, Qingyi; Wang, Xu‐Qing Angewandte Chemie, Vol. 133, Issue 17 https://doi.org/10.1002/ange.202100934	journal	March 2021
Highly Efficient Far Red/Near-Infrared Solid Fluorophores: Aggregation-Induced Emission, Intramolecular Charge Transfer, Twisted Molecular Conformation, and Bioimaging Applications Lu, Hongguang; Zheng, Yadan; Zhao, Xiaowei Angewandte Chemie International Edition, Vol. 55, Issue 1 https://doi.org/10.1002/anie.201507031	journal	November 2015
Aggregation-Induced Delayed Fluorescence Based on Donor/Acceptor-Tethered Janus Carborane Triads: Unique Photophysical Properties of Nondoped OLEDs Furue, Ryuhei; Nishimoto, Takuro; Park, In Seob Angewandte Chemie International Edition, Vol. 55, Issue 25 https://doi.org/10.1002/anie.201603232	journal	May 2016
Highly Efficient Nondoped OLEDs with Negligible Efficiency Roll-Off Fabricated from Aggregation-Induced Delayed Fluorescence Luminogens Huang, Jian; Nie, Han; Zeng, Jiajie Angewandte Chemie International Edition, Vol. 56, Issue 42 https://doi.org/10.1002/anie.201706752	journal	September 2017
AIE Triggers the Circularly Polarized Luminescence of Atomically Precise Enantiomeric Copper(I) Alkynyl Clusters Zhang, Miao‐Miao; Dong, Xi‐Yan; Wang, Zhao‐Yang Angewandte Chemie International Edition, Vol. 59, Issue 25 https://doi.org/10.1002/anie.201908909	journal	September 2019
Selective Synthesis of Conjugated Chiral Macrocycles: Sidewall Segments of (−)/(+)‐(12,4) Carbon Nanotubes with Strong Circularly Polarized Luminescence Wang, Jinyi; Zhuang, Guilin; Chen, Muqing Angewandte Chemie International Edition, Vol. 59, Issue 4 https://doi.org/10.1002/anie.201909401	journal	December 2019
ACQ‐to‐AIE Transformation: Tuning Molecular Packing by Regioisomerization for Two‐Photon NIR Bioimaging Li, Yuanyuan; Liu, Shunjie; Ni, Huwei Angewandte Chemie International Edition, Vol. 59, Issue 31 https://doi.org/10.1002/anie.202005785	journal	June 2020
Aggregation‐Induced Emission (AIE): A Historical Perspective Würthner, Frank Angewandte Chemie International Edition, Vol. 59, Issue 34 https://doi.org/10.1002/anie.202007525	journal	July 2020
500‐Fold Amplification of Small Molecule Circularly Polarised Luminescence through Circularly Polarised FRET Wade, Jessica; Brandt, Jochen R.; Reger, David Angewandte Chemie International Edition, Vol. 60, Issue 1 https://doi.org/10.1002/anie.202011745	journal	December 2020
AIE‐Active Chiral [3]Rotaxanes with Switchable Circularly Polarized Luminescence Li, Wei‐Jian; Gu, Qingyi; Wang, Xu‐Qing Angewandte Chemie International Edition, Vol. 60, Issue 17 https://doi.org/10.1002/anie.202100934	journal	March 2021
Axially Chiral Catenanes and π-Electron-Deficient Receptors Asakawa, Masumi; Ashton, Peter R.; Boyd, Sue E. Chemistry - A European Journal, Vol. 3, Issue 3 https://doi.org/10.1002/chem.19970030319	journal	January 2006
Circularly Polarized Luminescence of a Stereogenic Curved Paraphenylene Anchoring a Chiral Binaphthyl in Solution and Solid State Sato, Kenta; Hasegawa, Masashi; Nojima, Yuki Chemistry – A European Journal, Vol. 27, Issue 4 https://doi.org/10.1002/chem.202004283	journal	November 2020
Small Figure‐Eight Luminophores: Double‐Twisted Tethered Cyclic Binaphthyls Boost Circularly Polarized Luminescence Nojima, Yuki; Hasegawa, Masashi; Hara, Nobuyuki Chemistry – A European Journal, Vol. 27, Issue 19 https://doi.org/10.1002/chem.202005320	journal	February 2021
Circularly Polarized Luminescence: A Review of Experimental and Theoretical Aspects: CPL: EXPERIMENTS AND THEORY. A REVIEW Longhi, Giovanna; Castiglioni, Ettore; Koshoubu, Jun Chirality, Vol. 28, Issue 10 https://doi.org/10.1002/chir.22647	journal	September 2016
Aggregation‐Induced Emission: A Challenge for Computational Chemistry Taking TPA‐BMO as an Example** Thieulloy, Laure; Le Bras, Laura; Zumer, Benoît ChemPhysChem, Vol. 22, Issue 17 https://doi.org/10.1002/cphc.202100239	journal	July 2021
Circularly Polarized Luminescence and Circular Dichroisms in Small Organic Molecules: Correlation between Excitation and Emission Dissymmetry Factors Tanaka, Hiroki; Inoue, Yoshihisa; Mori, Tadashi ChemPhotoChem, Vol. 2, Issue 5 https://doi.org/10.1002/cptc.201800015	journal	March 2018
Circularly Polarized Luminescence in Chiral π‐Conjugated Macrocycles Hasegawa, Masashi; Nojima, Yuki; Mazaki, Yasuhiro ChemPhotoChem, Vol. 5, Issue 12 https://doi.org/10.1002/cptc.202100162	journal	September 2021
Chiral AIEgens – Chiral recognition, CPL materials and other chiral applications Hu, Ming; Feng, Hai-Tao; Yuan, Ying-Xue Coordination Chemistry Reviews, Vol. 416 https://doi.org/10.1016/j.ccr.2020.213329	journal	August 2020
Chirality and Chiroptics of Lanthanide Molecular and Supramolecular Assemblies Wong, Ho-Yin; Lo, Wai-Sum; Yim, King-Him Chem, Vol. 5, Issue 12 https://doi.org/10.1016/j.chempr.2019.08.006	journal	December 2019
Axially chiral propeller-shaped spiroborates with aggregation-modulated circularly polarized luminescence Duan, Wenzeng; Li, Kang; Ji, Honghan Dyes and Pigments, Vol. 193 https://doi.org/10.1016/j.dyepig.2021.109538	journal	September 2021
Supramolecular Ex plorations: Ex hibiting the Ex tent of Ex tended Cationic Cyclophanes Dale, Edward J.; Vermeulen, Nicolaas A.; Juríček, Michal Accounts of Chemical Research, Vol. 49, Issue 2 https://doi.org/10.1021/acs.accounts.5b00495	journal	January 2016
Aggregation-Induced Emission (AIE) Dots: Emerging Theranostic Nanolights Feng, Guangxue; Liu, Bin Accounts of Chemical Research, Vol. 51, Issue 6 https://doi.org/10.1021/acs.accounts.8b00060	journal	May 2018
Aggregation-Induced Emission: Together We Shine, United We Soar! Mei, Ju; Leung, Nelson L. C.; Kwok, Ryan T. K. Chemical Reviews, Vol. 115, Issue 21 https://doi.org/10.1021/acs.chemrev.5b00263	journal	October 2015
Sugar-Based Aggregation-Induced Emission Luminogens: Design, Structures, and Applications Wang, Yijia; Nie, Jingyi; Fang, Wen Chemical Reviews, Vol. 120, Issue 10 https://doi.org/10.1021/acs.chemrev.9b00814	journal	April 2020
3D Boranil Complexes with Aggregation-Amplified Circularly Polarized Luminescence Li, Kang; Ji, Honghan; Yang, Zeren The Journal of Organic Chemistry, Vol. 86, Issue 23 https://doi.org/10.1021/acs.joc.1c01956	journal	November 2021
Pyrene-Containing ortho-Oligo(phenylene)ethynylene Foldamer as a Ratiometric Probe Based on Circularly Polarized Luminescence Reiné, Pablo; Justicia, Jose; Morcillo, Sara P. The Journal of Organic Chemistry, Vol. 83, Issue 8 https://doi.org/10.1021/acs.joc.8b00162	journal	March 2018
Polyanionic Cyclodextrin-Induced Supramolecular Assembly of a Cationic Tetraphenylethylene Derivative with Aggregation-Induced Emission Kaur, Jasvir; Nadimetla, Dinesh N.; Bhosale, Sheshanath V. The Journal of Physical Chemistry B, Vol. 126, Issue 5 https://doi.org/10.1021/acs.jpcb.1c09780	journal	February 2022
Modeling the Modulation of Emission Behavior in E/Z Isomers of Dipyrrolyldiphenylethene: From Molecules to Nanoaggregates Le Bras, Laura; Adamo, Carlo; Perrier, Aurélie The Journal of Physical Chemistry C, Vol. 121, Issue 45 https://doi.org/10.1021/acs.jpcc.7b09310	journal	November 2017
High Brightness Circularly Polarized Organic Light-Emitting Diodes Based on Nondoped Aggregation-Induced Emission (AIE)-Active Chiral Binaphthyl Emitters Zhang, Xueyan; Zhang, Yu; Zhang, Haiping Organic Letters, Vol. 21, Issue 2 https://doi.org/10.1021/acs.orglett.8b03620	journal	December 2018
Tetraphenylethylene-Based AIE-Active Probes for Sensing Applications La, Duong Duc; Bhosale, Sidhanath V.; Jones, Lathe A. ACS Applied Materials & Interfaces, Vol. 10, Issue 15 https://doi.org/10.1021/acsami.7b12320	journal	October 2017
Creation of Efficient Blue Aggregation-Induced Emission Luminogens for High-Performance Nondoped Blue OLEDs and Hybrid White OLEDs Li, Yinghao; Xu, Zeng; Zhu, Xiangyu ACS Applied Materials & Interfaces, Vol. 11, Issue 19 https://doi.org/10.1021/acsami.9b03177	journal	April 2019
Achieving Circularly Polarized Surface Emitting Perovskite Microlasers with All-Dielectric Metasurfaces Dai, Wei; Wang, Yujie; Li, Ruixue ACS Nano, Vol. 14, Issue 12 https://doi.org/10.1021/acsnano.0c06463	journal	November 2020
Eutectogels as Matrices to Manipulate Supramolecular Chirality and Circularly Polarized Luminescence Cheng, Qiuhong; Hao, Aiyou; Xing, Pengyao ACS Nano, Vol. 16, Issue 4 https://doi.org/10.1021/acsnano.2c01731	journal	March 2022
Efficient Solid Emitters with Aggregation-Induced Emission and Intramolecular Charge Transfer Characteristics: Molecular Design, Synthesis, Photophysical Behaviors, and OLED Application Yuan, Wang Zhang; Gong, Yongyang; Chen, Shuming Chemistry of Materials, Vol. 24, Issue 8 https://doi.org/10.1021/cm300416y	journal	April 2012
Circularly polarized luminescence spectroscopy Riehl, James P.; Richardson, Frederick S. Chemical Reviews, Vol. 86, Issue 1, p. 1-16 https://doi.org/10.1021/cr00071a001	journal	February 1986
1,1‘-Binaphthyl Dimers, Oligomers, and Polymers: Molecular Recognition, Asymmetric Catalysis, and New Materials Pu, Lin Chemical Reviews, Vol. 98, Issue 7 https://doi.org/10.1021/cr970463w	journal	October 1998
Host-guest complexation. 22. Reciprocal chiral recognition between amino acids and dilocular systems Peacock, Stephen S.; Walba, David M.; Gaeta, Fred C. A. Journal of the American Chemical Society, Vol. 102, Issue 6 https://doi.org/10.1021/ja00526a046	journal	March 1980
Turn-On Fluorescence in Tetraphenylethylene-Based Metal–Organic Frameworks: An Alternative to Aggregation-Induced Emission Shustova, Natalia B.; McCarthy, Brian D.; Dincă, Mircea Journal of the American Chemical Society, Vol. 133, Issue 50 https://doi.org/10.1021/ja209327q	journal	December 2011
ExBox: A Polycyclic Aromatic Hydrocarbon Scavenger Barnes, Jonathan C.; Juríček, Michal; Strutt, Nathan L. Journal of the American Chemical Society, Vol. 135, Issue 1 https://doi.org/10.1021/ja307360n	journal	October 2012
Planar Chiral Tetrasubstituted [2.2]Paracyclophane: Optical Resolution and Functionalization Morisaki, Yasuhiro; Gon, Masayuki; Sasamori, Takahiro Journal of the American Chemical Society, Vol. 136, Issue 9 https://doi.org/10.1021/ja412197j	journal	February 2014
Mechanical-Bond-Induced Exciplex Fluorescence in an Anthracene-Based Homo[2]catenane Garci, Amine; Beldjoudi, Yassine; Kodaimati, Mohamad S. Journal of the American Chemical Society, Vol. 142, Issue 17 https://doi.org/10.1021/jacs.0c02128	journal	April 2020
Formation of Planar Chiral Platinum Triangles via Pillar[5]arene for Circularly Polarized Luminescence Zhu, Huangtianzhi; Li, Qi; Shi, Bingbing Journal of the American Chemical Society, Vol. 142, Issue 41 https://doi.org/10.1021/jacs.0c09598	journal	October 2020
Infinitene: A Helically Twisted Figure-Eight [12]Circulene Topoisomer Krzeszewski, Maciej; Ito, Hideto; Itami, Kenichiro Journal of the American Chemical Society, Vol. 144, Issue 2 https://doi.org/10.1021/jacs.1c10807	journal	December 2021
Helically Chiral Hybrid Cyclodextrin Metal–Organic Framework Exhibiting Circularly Polarized Luminescence Kazem-Rostami, Masoud; Orte, Angel; Ortuño, Ana M. Journal of the American Chemical Society, Vol. 144, Issue 21 https://doi.org/10.1021/jacs.2c01554	journal	May 2022
The Fixed Propeller-Like Conformation of Tetraphenylethylene that Reveals Aggregation-Induced Emission Effect, Chiral Recognition, and Enhanced Chiroptical Property Xiong, Jia-Bin; Feng, Hai-Tao; Sun, Jian-Ping Journal of the American Chemical Society, Vol. 138, Issue 36 https://doi.org/10.1021/jacs.6b07087	journal	August 2016
Binaphthyl–Bipyridyl Cyclic Dyads as a Chiroptical Switch Takaishi, Kazuto; Yasui, Makoto; Ema, Tadashi Journal of the American Chemical Society, Vol. 140, Issue 16 https://doi.org/10.1021/jacs.8b01860	journal	April 2018
ExTzBox: A Glowing Cyclophane for Live-Cell Imaging Roy, Indranil; Bobbala, Sharan; Zhou, Jiawang Journal of the American Chemical Society, Vol. 140, Issue 23 https://doi.org/10.1021/jacs.8b03066	journal	May 2018
Functionalized Acrylonitriles with Aggregation-Induced Emission: Structure Tuning by Simple Reaction-Condition Variation, Efficient Red Emission, and Two-Photon Bioimaging Niu, Guangle; Zheng, Xiuli; Zhao, Zheng Journal of the American Chemical Society, Vol. 141, Issue 38 https://doi.org/10.1021/jacs.9b06196	journal	August 2019
Enantioselective Recognition of Amino Acids by Axially-Chiral π-Electron-Deficient Receptors Asakawa, Masumi; Brown, Christopher L.; Pasini, Dario The Journal of Organic Chemistry, Vol. 61, Issue 21 https://doi.org/10.1021/jo961256j	journal	January 1996
Circularly polarized lanthanide luminescence for advanced security inks MacKenzie, Lewis E.; Pal, Robert Nature Reviews Chemistry, Vol. 5, Issue 2 https://doi.org/10.1038/s41570-020-00235-4	journal	December 2020
Mechanically interlocked pyrene-based photocatalysts Garci, Amine; Weber, Jacob A.; Young, Ryan M. Nature Catalysis, Vol. 5, Issue 6 https://doi.org/10.1038/s41929-022-00799-y	journal	June 2022
Circularly polarized laser emission induced in isotropic and achiral dye systems Cerdán, Luis; García-Moreno, Sara; Costela, Angel Scientific Reports, Vol. 6, Issue 1 https://doi.org/10.1038/srep28740	journal	June 2016
Limonene induced chiroptical generation and inversion during aggregation of achiral polyfluorene analogs: structure-dependence and mechanism Wang, Laibing; Suzuki, Nozomu; Liu, Jiangfei Polym. Chem., Vol. 5, Issue 20 https://doi.org/10.1039/C4PY00865K	journal	January 2014
Red emissive AIE luminogens with high hole-transporting properties for efficient non-doped OLEDs Qin, Wei; Lam, Jacky W. Y.; Yang, Zhiyong Chemical Communications, Vol. 51, Issue 34 https://doi.org/10.1039/C5CC01690H	journal	January 2015
Aggregation-induced emission of siloles Zhao, Zujin; He, Bairong; Tang, Ben Zhong Chemical Science, Vol. 6, Issue 10 https://doi.org/10.1039/C5SC01946J	journal	January 2015
From ACQ to AIE: the suppression of the strong π–π interaction of naphthalene diimide derivatives through the adjustment of their flexible chains Zong, Luyi; Xie, Yujun; Wang, Can Chemical Communications, Vol. 52, Issue 77 https://doi.org/10.1039/C6CC06176A	journal	January 2016
Stereogenic cyclic oligonaphthalenes displaying ring size-dependent handedness of circularly polarized luminescence (CPL) Nojima, Yuki; Hasegawa, Masashi; Hara, Nobuyuki Chemical Communications, Vol. 55, Issue 19 https://doi.org/10.1039/C8CC08929A	journal	January 2019
Macrocycles and cages based on tetraphenylethylene with aggregation-induced emission effect Feng, Hai-Tao; Yuan, Ying-Xue; Xiong, Jia-Bin Chemical Society Reviews, Vol. 47, Issue 19 https://doi.org/10.1039/C8CS00444G	journal	January 2018
Novel near-infrared II aggregation-induced emission dots for in vivo bioimaging Lin, Jiacheng; Zeng, Xiaodong; Xiao, Yuling Chemical Science, Vol. 10, Issue 4 https://doi.org/10.1039/C8SC04363A	journal	January 2019
Design of multi-functional AIEgens: tunable emission, circularly polarized luminescence and self-assembly by dark through-bond energy transfer Feng, Hai-Tao; Gu, Xinggui; Lam, Jacky W. Y. Journal of Materials Chemistry C, Vol. 6, Issue 33 https://doi.org/10.1039/C8TC02504E	journal	January 2018
Recent advances in circularly polarized electroluminescence based on organic light-emitting diodes Zhang, Da-Wei; Li, Meng; Chen, Chuan-Feng Chemical Society Reviews, Vol. 49, Issue 5 https://doi.org/10.1039/C9CS00680J	journal	January 2020
Multi-color tunable circularly polarized luminescence in one single AIE system Shang, Hongxing; Ding, Zeyang; Shen, Yue Chemical Science, Vol. 11, Issue 8 https://doi.org/10.1039/C9SC05643B	journal	January 2020
Strong CPL of achiral liquid crystal fluorescent polymer via the regulation of AIE-active chiral dopant Liu, Kerui; Shen, Yihao; Li, Xiaojing Chemical Communications, Vol. 56, Issue 84 https://doi.org/10.1039/D0CC05523A	journal	January 2020
Fluorescent cyclophanes and their applications Roy, Indranil; David, Arthur H. G.; Das, Partha Jyoti Chemical Society Reviews, Vol. 51, Issue 13 https://doi.org/10.1039/D0CS00352B	journal	January 2022
The design of responsive luminescent lanthanide probes and sensors Parker, David; Fradgley, Jack D.; Wong, Ka-Leung Chemical Society Reviews, Vol. 50, Issue 14 https://doi.org/10.1039/D1CS00310K	journal	January 2021
The fast-growing field of photo-driven theranostics based on aggregation-induced emission Zhang, Zhijun; Kang, Miaomiao; Tan, Hui Chemical Society Reviews, Vol. 51, Issue 6 https://doi.org/10.1039/D1CS01138C	journal	January 2022
Circularly polarized luminescence in chiral nematic liquid crystals: generation and amplification Yang, Xuefeng; Jin, Xue; Zhao, Tonghan Materials Chemistry Frontiers https://doi.org/10.1039/D1QM00335F	journal	January 2021
Chiral assembly of organic luminogens with aggregation-induced emission Liu, Chenchen; Yang, Jun-Cheng; Lam, Jacky W. Y. Chemical Science, Vol. 13, Issue 3 https://doi.org/10.1039/D1SC02305E	journal	January 2022
Aggregation-induced emission from silole-based lumophores embedded in organic–inorganic hybrid hosts Lyu, Guanpeng; Southern, Thomas J. F.; Charles, Bethan L. Journal of Materials Chemistry C, Vol. 9, Issue 39 https://doi.org/10.1039/D1TC02794H	journal	January 2021
Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole Luo, Jingdong; Xie, Zhiliang; Lam, Jacky W. Y. Chemical Communications, Issue 18 https://doi.org/10.1039/b105159h	journal	January 2001
Aggregation-induced emission: phenomenon, mechanism and applications Hong, Yuning; Lam, Jacky W. Y.; Tang, Ben Zhong Chemical Communications, Issue 29 https://doi.org/10.1039/b904665h	journal	January 2009
Chiral intertwined spirals and magnetic transition dipole moments dictated by cylinder helicity Sato, Sota; Yoshii, Asami; Takahashi, Satsuki Proceedings of the National Academy of Sciences, Vol. 114, Issue 50 https://doi.org/10.1073/pnas.1717524114	journal	November 2017
The energy gap law for radiationless transitions in large molecules Englman, Robert; Jortner, Joshua Molecular Physics, Vol. 18, Issue 2 https://doi.org/10.1080/00268977000100171	journal	February 1970
Measurement of the Circular Polarization of the Luminescence of Photoselected Samples under Artifact-Free Conditions Blok, P. M. L.; Dekkers, H. P. J. M. Applied Spectroscopy, Vol. 44, Issue 2 https://doi.org/10.1366/0003702904085679	journal	February 1990
Beyond Chiral Organic (p-Block) Chromophores for Circularly Polarized Luminescence: The Success of d-Block and f-Block Chiral Complexes Doistau, Benjamin; Jiménez, Juan-Ramón; Piguet, Claude Frontiers in Chemistry, Vol. 8 https://doi.org/10.3389/fchem.2020.00555	journal	July 2020

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Aggregation‐Induced Emission and Circularly Polarized Luminescence Duality in Tetracationic Binaphthyl‐Based Cyclophanes

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Aggregation-Induced Emission and Circularly Polarized Luminescence Duality in Tetracationic Binaphthyl-Based Cyclophanes

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