Circularly Polarized Luminescence from Chiral Conjugated Poly(carbazole- ran -acridine)s with Aggregation-Induced Emission and Delayed Fluorescence
Abstract
Pure organic materials with circularly polarized luminescence (CPL) and delayed fluorescence have gained increasing interest from academic and technological areas. To enhance the solid-state emission and exciton utilization in chiral optoelectronic devices, a synthetic strategy to impart conjugated polymers with CPL and aggregation-induced delayed fluorescence was proposed. Herein, two conjugated macromolecules with electron-donating poly(carbazole- ran -acridine) backbones, electron-withdrawing dibenzothiophen-2-yl(phenyl)methanone, and chiral alanine moieties were designed and synthesized. Their neat films exhibited strong green emission with quantum yields of 6.7 and 10.3% and delayed fluorescence with a lifetime of 1.358 and 1.366 μs, respectively. Both the Cotton effect and CPL with a dissymmetry factor of −2.01 × 10 –3 and −1.39 × 10 –3 were determined in the solid state. Such unique conjugated polymers were employed as solution-processed emitting layers in organic light emitting diodes, which displayed a maximum brightness of 1477 cd/m 2 and maximum current efficiency of 2.52 cd/A.
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Aggregation-Induced Emission: Together We Shine, United We Soar!
Mei, J., Leung, N. L. C., Kwok, R. T. K., Lam, J. W. Y., & Tang, B. Z. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00263 · Cited by 8,270 · see citing works
Self-citationElectroluminescence in conjugated polymers
Friend, R. H., Gymer, R. W., Holmes, A. B., Burroughes, J. H., Marks, R. N., Taliani, C., Bradley, D. D. C., dos Santos, D. A., Brédas, J., Lögdlund, M., et al. (1999) · Nature · doi:10.1038/16393 · Cited by 5,997 · see citing works
Gold Helix Photonic Metamaterial as Broadband Circular Polarizer
Gansel, J. K., Thiel, M., Rill, M. S., Decker, M., Bade, K. J., Saile, V., von Freymann, G., Lindén, S., & Wegener, M. (2009) · Science · doi:10.1126/science.1177031 · Cited by 2,700 · see citing works
Efficient blue organic light-emitting diodes employing thermally activated delayed fluorescence
Zhang, Q., Li, B., Huang, S., Nomura, H., Tanaka, H., & Adachi, C. (2014) · Nature Photonics · doi:10.1038/nphoton.2014.12 · Cited by 2,434 · see citing works
Recent advances in organic thermally activated delayed fluorescence materials
Yang, Z., Mao, Z., Xie, Z., Zhang, Y., Liu, S., Zhao, J., Xu, J., Chi, Z., & Aldred, M. P. (2017) · Chemical Society Reviews · doi:10.1039/c6cs00368k · Cited by 2,395 · see citing works
Purely Organic Thermally Activated Delayed Fluorescence Materials for Organic Light‐Emitting Diodes
Wong, M. Y., & Zysman‐Colman, E. (2017) · Advanced Materials · doi:10.1002/adma.201605444 · Cited by 2,053 · see citing works
Thermally Activated Delayed Fluorescence Materials Towards the Breakthrough of Organoelectronics
Tao, Y., Yuan, K., Chen, T., Xu, P., Li, H., Chen, R., Zheng, C., Zhang, L., & Huang, W. (2014) · Advanced Materials · doi:10.1002/adma.201402532 · Cited by 2,002 · see citing works
Zhang, Q., Li, J., Shizu, K., Huang, S., Hirata, S., Miyazaki, H., & Adachi, C. (2012) · Journal of the American Chemical Society · doi:10.1021/ja306538w · Cited by 1,609 · see citing works
Highly efficient blue electroluminescence based on thermally activated delayed fluorescence
Hirata, S., Sakai, Y., Masui, K., Tanaka, H., Lee, S. Y., Nomura, H., Nakamura, N., Yasumatsu, M., Nakanotani, H., Zhang, Q., et al. (2014) · Nature Materials · doi:10.1038/nmat4154 · Cited by 1,328 · see citing works
A Broadband, Background-Free Quarter-Wave Plate Based on Plasmonic Metasurfaces
Yu, N., Aieta, F., Genevet, P., Kats, M. A., Gaburro, Z., & Capasso, F. (2012) · Nano Letters · doi:10.1021/nl303445u · Cited by 1,222 · see citing works
Electrically Switchable Chiral Light-Emitting Transistor
Zhang, Y., Oka, T., Suzuki, R., Ye, J. T., & Iwasa, Y. (2014) · Science · doi:10.1126/science.1251329 · Cited by 776 · see citing works
Lasing in a three-dimensional photonic crystal of the liquid crystal blue phase II
Cao, W., Muñoz, A., Palffy‐Muhoray, P., et al. (2002) · Nature Materials · doi:10.1038/nmat727 · Cited by 567 · see citing works
Brandt, J. R., Wang, X., Yang, Y., et al. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b02463 · Cited by 547 · see citing works
Circularly Polarized Electroluminescence from a Polymer Light-Emitting Diode
Peeters, E., Christiaans, M. P. T., Janssen, R. A. J., Schoo, H. F. M., Dekkers, H. P. J. M., & Meijer, E. W. (1997) · Journal of the American Chemical Society · doi:10.1021/ja971912c · Cited by 531 · see citing works
Li, M., Li, S., Zhang, D., et al. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201800198 · Cited by 471 · see citing works
Guo, J., Li, X., Nie, H., Luo, W., Gan, S., Hu, S., Hu, R., Qin, A., Zhao, Z., Su, S., et al. (2017) · Advanced Functional Materials · doi:10.1002/adfm.201606458 · Cited by 444 · see citing works
Self-citationSong, F., Xu, Z., Zhang, Q., Zhao, Z., Zhang, H., Zhao, W., Qiu, Z., Qi, C., Zhang, H., Sung, H. H. Y., et al. (2018) · Advanced Functional Materials · doi:10.1002/adfm.201800051 · Cited by 433 · see citing works
Self-citationDesign of Lanthanide‐Based OLEDs with Remarkable Circularly Polarized Electroluminescence
Zinna, F., Pasini, M., Galeotti, F., et al. (2016) · Advanced Functional Materials · doi:10.1002/adfm.201603719 · Cited by 424 · see citing works
Shao, S., Hu, J. H., Wang, X., et al. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.7b10257 · Cited by 424 · see citing works
Liu, J., Su, H., Meng, L., Zhao, Y., Deng, C., Ng, J. C. Y., Lü, P., Mahtab, F., Lam, J. W. Y., Huang, X., et al. (2012) · Chemical Science · doi:10.1039/c2sc20382k · Cited by 389 · see citing works
Self-citationHuang, J., Nie, H., Zeng, J., Zhuang, Z., Gan, S., Cai, Y., Guo, J., Su, S., Zhao, Z., & Tang, B. Z. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201706752 · Cited by 385 · see citing works
Self-citationDevelopment of a New Mesoporous Carbon Using an HMS Aluminosilicate Template
Lee, J., Yoon, S., Oh, S. M., Shin, C., & Hyeon, T. (2000) · Advanced Materials · doi:10.1002/(sici)1521-4095(200003)12:5 · Cited by 380 · see citing works
Miniature chiral beamsplitter based on gyroid photonic crystals
Turner, M. D., Saba, M., Zhang, Q., et al. (2013) · Nature Photonics · doi:10.1038/nphoton.2013.233 · Cited by 344 · see citing works
Circularly‐Polarized Luminescence (CPL) from Chiral AIE Molecules and Macrostructures
Roose, J., Tang, B. Z., & Wong, K. S. (2016) · Small · doi:10.1002/smll.201601455 · Cited by 324 · see citing works
Self-citationOptical Polarization in Biomedical Applications
Tuchin, V. V., Novikova, T., Wang, L. V., Zimnyakov, D. A., Ma, H., Васильевна, А. М., & Wan, J. (2006) · Springer series in biophysics · doi:10.1007/978-3-032-16073-7 · Cited by 293 · see citing works
Nuzzo, D. D., Kulkarni, C. H., Zhao, B., et al. (2017) · ACS Nano · doi:10.1021/acsnano.7b07390 · Cited by 276 · see citing works
Imai, Y., Nakano, Y., Kawai, T., et al. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201803833 · Cited by 274 · see citing works
Binaphthyl–Bipyridyl Cyclic Dyads as a Chiroptical Switch
Takaishi, K., Yasui, M., & Ema, T. (2018) · Journal of the American Chemical Society · doi:10.1021/jacs.8b01860 · Cited by 246 · see citing works
Control of Circularly Polarized Electroluminescence in Induced Twist Structure of Conjugate Polymer
Lee, D., Song, J., Lee, Y., et al. (2017) · Advanced Materials · doi:10.1002/adma.201700907 · Cited by 245 · see citing works
Xie, G., Luo, J., Huang, M., et al. (2017) · Advanced Materials · doi:10.1002/adma.201604223 · Cited by 227 · see citing works
Huang, J., Su, J., Li, X., et al. (2011) · Journal of Materials Chemistry · doi:10.1039/c0jm03300f · Cited by 196 · see citing works
Shao, S., Ding, J., Wang, L., et al. (2012) · Journal of the American Chemical Society · doi:10.1021/ja310158j · Cited by 147 · see citing works
Yang, Y., Wang, S., Zhu, Y., et al. (2018) · Advanced Functional Materials · doi:10.1002/adfm.201706916 · Cited by 141 · see citing works
Construction of efficient blue AIE emitters with triphenylamine and TPE moieties for non-doped OLEDs
Huang, J., Jiang, Y., Yang, J., Tang, R., Xie, N., Li, Q., Kwok, H. S., Tang, B. Z., & Li, Z. (2013) · Journal of Materials Chemistry C · doi:10.1039/c3tc32207f · Cited by 134 · see citing works
Self-citationFreeman, D. M. E., Musser, A. J., Frost, J. M., et al. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.7b03327 · Cited by 130 · see citing works
Zhu, Y., Zhang, Y., Yao, B., et al. (2016) · Macromolecules · doi:10.1021/acs.macromol.6b00430 · Cited by 119 · see citing works
Liu, J., Cheng, Y., Xie, Z., et al. (2008) · Advanced Materials · doi:10.1002/adma.200701705 · Cited by 118 · see citing works
Zhu, W., Hu, M. J., Yao, R., et al. (2003) · Journal of Photochemistry and Photobiology A Chemistry · doi:10.1016/s1010-6030(02)00325-8 · Cited by 113 · see citing works
Wang, Z., Feng, Y., Wang, N., Cheng, Y., Quan, Y., & Ju, H. (2018) · The Journal of Physical Chemistry Letters · doi:10.1021/acs.jpclett.8b02087 · Cited by 100 · see citing works
Liu, Q., Xia, Q., Wang, S., Li, B. S., & Tang, B. Z. (2018) · Journal of Materials Chemistry C · doi:10.1039/c8tc00838h · Cited by 95 · see citing works
Self-citationFeng, H., Zhang, X., & Zheng, Y. (2015) · The Journal of Organic Chemistry · doi:10.1021/acs.joc.5b01194 · Cited by 93 · see citing works
Liu, X., Jiao, J., Jiang, X., Li, J., Cheng, Y., & Zhu, C. (2013) · Journal of Materials Chemistry C · doi:10.1039/c3tc30886c · Cited by 87 · see citing works
Doping-free circularly polarized electroluminescence of AIE-active chiral binaphthyl-based polymers
Yang, L., Zhang, Y., Zhang, X., Li, N., Quan, Y., & Cheng, Y. (2018) · Chemical Communications · doi:10.1039/c8cc05153d · Cited by 86 · see citing works
A Self-Replicating Peptide under Ionic Control
Yao, S. Q., Ghosh, I., Zutshi, R., & Chmielewski, J. A. (1998) · Angewandte Chemie International Edition · doi:10.1002/(sici)1521-3773(19980302)37:4 · Cited by 85 · see citing works
Red emissive AIE luminogens with high hole-transporting properties for efficient non-doped OLEDs
Qin, W., Lam, J. W. Y., Yang, Z., Chen, S., Liang, G., Zhao, W., Kwok, H. S., & Tang, B. Z. (2015) · Chemical Communications · doi:10.1039/c5cc01690h · Cited by 80 · see citing works
Self-citationCheng, S.-W., Han, T., Huang, T.-Y., et al. (2018) · Polymer Chemistry · doi:10.1039/c8py00809d · Cited by 75 · see citing works
Aizawa, N., Tsou, C.-J., Park, I. S., & Yasuda, T. (2016) · Polymer Journal · doi:10.1038/pj.2016.82 · Cited by 71 · see citing works
Xiong, J., Xie, W.-Z., Sun, J.-P., Wang, J., Zhu, Z.-H., Feng, H., Guo, D., Zhang, H., & Zheng, Y. (2016) · The Journal of Organic Chemistry · doi:10.1021/acs.joc.6b00371 · Cited by 62 · see citing works
Self-citationSynthesis and tunable chiroptical properties of chiral BODIPY-based D–π–A conjugated polymers
Ma, X., Azeem, E. A., Liu, X., et al. (2013) · Journal of Materials Chemistry C · doi:10.1039/c3tc32029d · Cited by 58 · see citing works
Thermally Activated Delayed Fluorescence Host for High Performance Organic Light-Emitting Diodes
Zhang, L., & Cheah, K. W. (2018) · Scientific Reports · doi:10.1038/s41598-018-27238-y · Cited by 42 · see citing works
Monitoring of the ADP/ATP Ratio by Induced Circularly Polarised Europium Luminescence
Shuvaev, S., Fox, M. A., & Parker, D. (2018) · Angewandte Chemie · doi:10.1002/ange.201801248 · Cited by 31 · see citing works
Feng, L., Wang, C., Deng, X., et al. (2017) · Materials Chemistry Frontiers · doi:10.1039/c7qm00404d · Cited by 25 · see citing works
Synthesis and fluorescence study of conjugated polymers based on 2,4,6-triphenylpyridine moieties
Ran, Q., Ma, J., Wang, T., Fan, S., Yang, Y., Qi, S., Cheng, Y., & Song, F. (2016) · New Journal of Chemistry · doi:10.1039/c5nj03722k · Cited by 14 · see citing works
Self-citationAggregation-induced delayed fluorescence (AIDF) materials: a new break-through for nondoped OLEDs
Bryce, M. R. (2017) · Science China Chemistry · doi:10.1007/s11426-017-9161-4 · Cited by 14 · see citing works
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- Authors
- Hu, Y., Song, F., Xu, Z., Tu, Y., Zhang, H., Cheng, Q., Lam, J. W. Y., Ma, D., & Tang, B. Z.
- Affiliations
- Hong Kong University of Science and Technology (HK)
- State Key Laboratory of Luminescent Materials and Devices (CN)
- Department of Chemistry, The Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration and Reconstruction and Institute for Advanced Study, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong 999077, China
- Corresponding author
- Lam, Jacky W.Y.
- Ma, Dongge
- Tang, Ben Zhong
- Venue
- ACS Applied Polymer Materials
- Publisher
- American Chemical Society (ACS)
- Published
- 2019-01-07
- Volume
- 1
- Issue
- 2
- Pages
- 221-229
- ISSN
- 2637-6105 (ISSN-L)
- OpenAlex
- W2909459070
- Cited by
- 48
- References
- 54
- Citations by year
- 2026: 3 · 2025: 4 · 2024: 8 · 2023: 6 · 2022: 9 · 2021: 6 · 2020: 10 · 2019: 2
- FWCI
- 2.43
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- ACS Applied Polymer Materials (publishedVersion)
- Rare & Special e-Zone (The Hong Kong University of Science and Technology) (submittedVersion)
- Funders
- Research Grants Council, University Grants Committee (16303815, C6009-17G, A-HKUST605/16, 16308116, C2014-15G)
- Innovation and Technology Commission (ITS/254/17, ITC-CNERC149C01)
- National Natural Science Foundation of China (21490570, 21490574, 21788102, 51508242)
- Guangzhou Municipality (201704030069)
- Shenzhen Municipality (JCY20170307173739739, JCYJ20170818113602462, JCYJ20160229205601482)
- Topics
- Physical Sciences › Engineering › Electrical and Electronic Engineering › Organic Light-Emitting Diodes Research
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Engineering › Electrical and Electronic Engineering › Organic Electronics and Photovoltaics
- Keywords
- circularly polarized luminescence, aggregation-induced emission, delayed fluorescence, chiral conjugated polymers, organic light-emitting diodes, Cotton effect, asymmetry factor, exciton utilization
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