Highly efficient aggregation-induced red-emissive organic thermally activated delayed fluorescence materials with prolonged fluorescence lifetime for time-resolved luminescence bioimaging
Abstract
Organic thermally activated delayed fluorescence (TADF) materials are emerging as potential candidates for time-resolved fluorescence imaging in biological systems. However, the development of purely organic TADF materials with bright aggregated-state emissions in the red/near-infrared (NIR) region remains challenging. Here, we report three donor–acceptor-type TADF molecules as promising candidates for time-resolved fluorescence imaging, which are engineered by direct connection of electron-donating moieties (phenoxazine or phenothiazine) and an electron-acceptor 1,8-naphthalimide (NI). Theoretically and experimentally, we elucidate that three TADF materials possessed remarkably small Δ E ST to promote the occurrence of reverse intersystem crossing (RISC). Moreover, they all exhibit aggregation-induced red emissions and long delayed fluorescence lifetimes without the influence of molecular oxygen. More importantly, these long-lived and biocompatible TADF materials, especially the phenoxazine-substituted NI fluorophores, show great potential for high-contrast fluorescence lifetime imaging in living cells. This study provides further a molecular design strategy for purely organic TADF materials and expands the versatile biological application of long-lived fluorescence research in time-resolved luminescence imaging.
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Organic molecules with small HOMO and LUMO orbital overlaps have a small singlet-triplet energy gap (ΔEST) because of small exchange energy between them, thus making it easy to induce TADF.
“Existing studies show that organic molecules with small HOMO and LUMO orbital overlaps have a small singlet-triplet energy gap (▵EST) because of small exchange energy between them, thus making it easy to induce TADF [38,39].”
From Red-light excited efficient metal-free near-infrared room-temperature phosphorescent films (2022) · cites this paper as [38]
Cites
Highly efficient organic light-emitting diodes from delayed fluorescence
Uoyama, H., Goushi, K., Shizu, K., Nomura, H., & Adachi, C. (2012) · Nature · doi:10.1038/nature11687 · Cited by 8,219 · 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
Fluorescent chemosensors: the past, present and future
Wu, D., Sedgwick, A. C., Gunnlaugsson, T., Akkaya, E. U., Yoon, J., & James, T. D. (2017) · Chemical Society Reviews · doi:10.1039/c7cs00240h · Cited by 2,013 · see citing works
Self-citationThermally 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
Reaction-based small-molecule fluorescent probes for chemoselective bioimaging
Chan, J., Dodani, S. C., & Chang, C. J. (2012) · Nature Chemistry · doi:10.1038/nchem.1500 · Cited by 1,890 · see citing works
Yuan, L., Lin, W., Zheng, K., He, L., & Huang, W. (2012) · Chemical Society Reviews · doi:10.1039/c2cs35313j · Cited by 1,827 · see citing works
Phosphorescent heavy-metal complexes for bioimaging
Zhao, Q., Huang, C., & Li, F. (2011) · Chemical Society Reviews · doi:10.1039/c0cs00114g · Cited by 1,262 · see citing works
Fluorescent Probes for Sensing and Imaging within Specific Cellular Organelles
Zhu, H., Fan, J., Du, J., & Peng, X. (2016) · Accounts of Chemical Research · doi:10.1021/acs.accounts.6b00292 · Cited by 987 · see citing works
Long-Lived Emissive Probes for Time-Resolved Photoluminescence Bioimaging and Biosensing
Zhang, K. Y., Yu, Q., Wei, H., Liu, S., Zhao, Q., & Huang, W. (2018) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00425 · Cited by 922 · see citing works
Lighting the way to see inside the live cell with luminescent transition metal complexes
Baggaley, E., Weinstein, J. A., & Williams, J. A. G. (2012) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2012.03.018 · Cited by 474 · see citing works
Chromogenic/Fluorogenic Ensemble Chemosensing Systems
Wu, J., Kwon, B., Liu, W., Anslyn, E. V., Wang, P., & Kim, J. S. (2015) · Chemical Reviews · doi:10.1021/cr500553d · Cited by 407 · see citing works
A selective fluorescent ratiometric chemodosimeter for mercury ion
Liu, B., & Tian, H. (2005) · Chemical Communications · doi:10.1039/b501913c · Cited by 381 · see citing works
Wu, D., Chen, L., Lee, W., Ko, G., Yin, J., & Yoon, J. (2017) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2017.06.011 · Cited by 335 · see citing works
Self-citationXiong, X., Song, F., Wang, J., Zhang, Y., Xue, Y., Sun, L., Jiang, N., Gao, P., Tian, L., & Peng, X. (2014) · Journal of the American Chemical Society · doi:10.1021/ja502292p · Cited by 326 · see citing works
Xie, G., Li, X., Chen, D., Wang, Z., Cai, X., Chen, D., Li, Y., Liu, K., Cao, Y., & Su, S. (2015) · Advanced Materials · doi:10.1002/adma.201503225 · Cited by 318 · see citing works
Recognition Moieties of Small Molecular Fluorescent Probes for Bioimaging of Enzymes
Wu, X., Shi, W. S., Li, X., & Ma, H. (2019) · Accounts of Chemical Research · doi:10.1021/acs.accounts.9b00214 · Cited by 287 · see citing works
AIE luminogens as fluorescent bioprobes
Niu, G., Zhang, R., Shi, X., Park, H., Xie, S., Kwok, R. T. K., Lam, J. W. Y., & Tang, B. Z. (2019) · TrAC Trends in Analytical Chemistry · doi:10.1016/j.trac.2019.115769 · Cited by 226 · see citing works
Self-citationNiu, G., Zheng, X., Zhao, Z., Zhang, H., Wang, J., He, X., Chen, Y., Shi, X., Ma, C., Kwok, R. T. K., et al. (2019) · Journal of the American Chemical Society · doi:10.1021/jacs.9b06196 · Cited by 183 · see citing works
Self-citationZhu, Z., Tian, D., Gao, P., Wang, K., Li, Y., Shu, X., Zhu, J., & Zhao, Q. (2018) · Journal of the American Chemical Society · doi:10.1021/jacs.8b08438 · Cited by 170 · see citing works
Recent Progress in Time‐Resolved Biosensing and Bioimaging Based on Lanthanide‐Doped Nanoparticles
Ma, Q., Wang, J., Li, Z., Lv, X., Liang, L., & Yuan, Q. (2019) · Small · doi:10.1002/smll.201804969 · Cited by 163 · see citing works
Ni, F., Zhu, Z., Tong, X., Xie, M., Zhao, Q., Zhong, C., Zou, Y., & Yang, C. (2018) · Chemical Science · doi:10.1039/c8sc01485j · Cited by 142 · see citing works
Li, T., Yang, D., Zhai, L., Wang, S., Zhao, B., Fu, N., Wang, L., Tao, Y., & Huang, W. (2017) · Advanced Science · doi:10.1002/advs.201600166 · Cited by 138 · see citing works
Ni, F., Li, N., Zhan, L., & Yang, C. (2020) · Advanced Optical Materials · doi:10.1002/adom.201902187 · Cited by 135 · see citing works
Shi, H., Zou, L., Huang, K., Wang, H., Sun, C., Wang, S., Ma, H., He, Y., Wang, J., Yu, H., et al. (2019) · ACS Applied Materials & Interfaces · doi:10.1021/acsami.9b01615 · Cited by 123 · see citing works
Ni, F., Zhu, Z., Tong, X., Zeng, W., An, K., Wei, D., Gong, S., Zhao, Q., Zhou, X., & Yang, C. (2019) · Advanced Science · doi:10.1002/advs.201801729 · Cited by 107 · see citing works
Brennecke, B., Wang, Q., Zhang, Q., et al. (2020) · Angewandte Chemie International Edition · doi:10.1002/anie.202002391 · Cited by 106 · see citing works
Gan, S., Zhou, J. Q., Smith, T. A., Su, H., Luo, W., Hong, Y., Zhao, Z., & Tang, B. Z. (2017) · Materials Chemistry Frontiers · doi:10.1039/c7qm00286f · Cited by 103 · see citing works
Grichine, A., Haefelé, A., Pascal, S., Alain Duperray, B., Michel, R., Andraud, C., & Maury, O. (2014) · Chemical Science · doi:10.1039/c4sc00473f · Cited by 97 · see citing works
Xiao, Y.-F., Chen, J.-X., Li, S., Tao, W.-W., Tian, S., Wang, K., Cui, X., Huang, Z., Zhang, X.-H., & Lee, C.-S. (2020) · Chemical Science · doi:10.1039/c9sc05817f · Cited by 84 · see citing works
Zhang, J., Chen, W., Kalytchuk, S., Li, K., Chen, R., Adachi, C., Chen, Z., Rogach, A. L., Zhu, G., Yu, K. N., et al. (2016) · ACS Applied Materials & Interfaces · doi:10.1021/acsami.6b03259 · Cited by 74 · see citing works
Zhang, Q., Xu, S., Li, M., Wang, Y., Zhang, N., Guan, Y., Chen, M., Chen, C.-F., & Hu, H.-Y. (2019) · Chemical Communications · doi:10.1039/c9cc00898e · Cited by 73 · see citing works
Hu, W., Guo, L., Bai, L., Miao, X., Ni, Y., Wang, Q., Zhao, H., Xie, M., Li, L., Lü, X., et al. (2018) · Advanced Healthcare Materials · doi:10.1002/adhm.201800299 · Cited by 69 · see citing works
Paisley, N. R., Tonge, C. M., & Hudson, Z. M. (2020) · Frontiers in Chemistry · doi:10.3389/fchem.2020.00229 · Cited by 67 · see citing works
King, S. M., Claire, S., Teixeira, R. I., Dosumu, A. N., Carrod, A. J., Dehghani, H., Hannon, M. J., Ward, A. D., Bicknell, R., Botchway, S. W., et al. (2018) · Journal of the American Chemical Society · doi:10.1021/jacs.8b05105 · Cited by 59 · see citing works
Hearn, K. N., Nalder, T. D., Cox, R. P., et al. (2017) · Chemical Communications · doi:10.1039/c7cc07922b · Cited by 50 · see citing works
Zhu, Z., Song, B., Yuan, J., et al. (2016) · Advanced Science · doi:10.1002/advs.201600146 · Cited by 46 · see citing works
Protein-Induced Long Lifetime Luminescence of Nonmetal Probes
Enkvist, E., Vaasa, A., Kasari, M., et al. (2011) · ACS Chemical Biology · doi:10.1021/cb200120v · Cited by 44 · see citing works
Xiong, X., Zheng, L., Yan, J., Ye, F., Qian, Y., & Song, F. (2015) · RSC Advances · doi:10.1039/c5ra08539j · Cited by 40 · see citing works
Tu, C., Awasthi, K., Chen, K.-P., et al. (2017) · ACS Photonics · doi:10.1021/acsphotonics.7b00188 · Cited by 38 · see citing works
Wu, Y., Song, F., Luo, W., Liu, Z., Song, B., & Peng, X. (2016) · ChemPhotoChem · doi:10.1002/cptc.201600027 · Cited by 33 · see citing works
A single component self-assembled thermally activated delayed fluorescence nanoprobe
Rao, W., Zhang, L., Xu, S., Zhang, Q., Yong-xiu, Q., & Hu, H. (2020) · Chemical Communications · doi:10.1039/c9cc09957c · Cited by 28 · see citing works
Sarkar, S. K., Pegu, M., Behera, S. K., Narra, S. K., & Thilagar, P. (2019) · Chemistry - An Asian Journal · doi:10.1002/asia.201901138 · Cited by 27 · see citing works
Hwang, J., Lee, C., Jeong, J., et al. (2020) · ACS Applied Materials & Interfaces · doi:10.1021/acsami.9b20279 · Cited by 27 · see citing works
Wu, Y., Jiao, L., Song, F., Chen, M., Liu, D., Yang, W., Sun, Y., Hong, G., Liu, L., & Peng, X. (2019) · Chemical Communications · doi:10.1039/c9cc07704a · Cited by 23 · see citing works
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Red-light excited efficient metal-free near-infrared room-temperature phosphorescent films
Sun, S., Ma, L., Wang, J., Ma, X., & Tian, H. (2022) · National Science Review · doi:10.1093/nsr/nwab085 · Cited by 108 · see citing works
“The delayed emission located at 600–700 nm, which is on a par with the fluorescence emission location and shape of the prompted emission, was classified as thermally activated delayed fluorescence (TADF) emission.”
BackgroundInfluential
- Authors
- Qi, S., Kim, S., Nguyen, V.-N., Kim, Y., Niu, G., Kim, G., Kim, S.-J., Park, S., & Yoon, J.
- Affiliations
- Ewha Womans University (KR)
- Department of Chemistry and Nanoscience, Ewha Womans University, Seoul 03760, Republic of Korea
- Shandong University (CN)
- Korea University (KR)
- Corresponding author
- Park, Sungnam
- Yoon, Juyoung
- ORCID
- Venue
- ACS Applied Materials & Interfaces
- Publisher
- American Chemical Society (ACS)
- Published
- 2020-11-06
- Volume
- 12
- Issue
- 46
- Pages
- 51293-51301
- ISSN
- 1944-8244 (ISSN-L)
- 1944-8252
- OpenAlex
- W3096899321
- Cited by
- 112
- References
- 45
- Citations by year
- 2026: 13 · 2025: 16 · 2024: 27 · 2023: 17 · 2022: 17 · 2021: 22
- FWCI
- 5.44
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- ACS Applied Materials & Interfaces (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Research Foundation of Korea (2012R1A3A2048814, 2019R1A6A1A11044070, 2020R 1A 6C 101B194)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Engineering › Electrical and Electronic Engineering › Organic Light-Emitting Diodes Research
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
- Keywords
- thermally activated delayed fluorescence, aggregation-induced emission, time-resolved fluorescence imaging, fluorescence lifetime imaging, donor-acceptor molecules, phenoxazine, phenothiazines, 1,8-naphthalimide, reverse intersystem crossing, oxygen tolerance, live-cell imaging, molecular design
- MeSH terms
- Biocompatible Materials, Cell Survival, Fluorescent Dyes, HeLa Cells, Humans, Microscopy, Fluorescence, Oxazines, Quantum Theory, Spectrometry, Fluorescence, Temperature, Naphthalimides
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