Phosphine Oxides Manipulate Aggregation‐Induced Delayed Fluorescence for Time‐Resolved Bioimaging
Open accessAbstract
Delayed fluorescence (DF) materials have shown great potential in time‐resolved luminescence imaging (TRLI), due to the relatively elongated emission lifetimes. However, the sensitivity of DF to environmental quenching leads to a challenge to realize TRLI directly using pure thermally‐activated DF (TADF) molecules. Herein, two TADF molecules, namely CzPOTCF and tBCzPOTCF, are designed and synthesized, featuring a diphenylphosphine oxide (DPPO) group substituted at the ortho‐position of the carbazole group. Compared with DPPO‐free CzTCF, the steric hindrance of DPPO groups enlarges dihedral angles between TCF and the carbazole groups in CzPOTCF and tBCzPOTCF; meanwhile, PO provides other channels for forming intermolecular hydrogen bonds. The optimized intermolecular interactions facilitate the dimer formation of CzPOTCF and tBCzPOTCF, which simultaneously enhance aggregation‐induced DF and mitigate disordered packing‐induced quenching. As a consequence, CzPOTCF and tBCzPOTCF show the enhanced aggregation‐induced DF with largely increased lifetimes. Without any additional assistance, the long‐lived fluorescence of CzPOTCF and tBCzPOTCF is successfully observed for cell TRLI, with 1–1.7 μs elongated average lifetimes of 6.69 and 7.41 μs, respectively.
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
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
Fluorescence Lifetime Measurements and Biological Imaging
Berezin, M. Y., & Achilefu, S. A. (2010) · Chemical Reviews · doi:10.1021/cr900343z · Cited by 2,401 · 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
Luminescent Chemodosimeters for Bioimaging
Yang, Y., Zhao, Q., Feng, W., & Li, F. (2012) · Chemical Reviews · doi:10.1021/cr2004103 · Cited by 2,236 · see citing works
Self-citationNew Strategies for Fluorescent Probe Design in Medical Diagnostic Imaging
Kobayashi, H., Ogawa, M., Alford, R. E., Choyke, P. L., & Urano, Y. (2009) · Chemical Reviews · doi:10.1021/cr900263j · Cited by 2,205 · 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
Self-citationGuo, 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
Huang, 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
Xiong, 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
Single Cell Optical Imaging and Spectroscopy
Stender, A. S., Marchuk, K., Liu, C., Sander, S., Meyer, M. W., Smith, E. A., Neupane, B. B., Wang, G., Li, J., Cheng, J., et al. (2013) · Chemical Reviews · doi:10.1021/cr300336e · Cited by 293 · see citing works
Zhu, 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
Self-citationZhao, B., Wang, H., Han, C., Ma, P., Li, Z., Chang, P., & Xu, H. (2020) · Angewandte Chemie International Edition · doi:10.1002/anie.202008885 · Cited by 149 · see citing works
Self-citationNi, 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
Self-citationZhang, J., Chen, R., Zhu, Z., Adachi, C., Zhang, X., & Lee, C. (2015) · ACS Applied Materials & Interfaces · doi:10.1021/acsami.5b08539 · Cited by 138 · 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
Self-citationNi, F., Li, N., Zhan, L., & Yang, C. (2020) · Advanced Optical Materials · doi:10.1002/adom.201902187 · Cited by 135 · see citing works
Li, X., Baryshnikov, G., Deng, C., Bao, X., Wu, B., Zhou, Y., Ågren, H., & Zhu, L. (2019) · Nature Communications · doi:10.1038/s41467-019-08684-2 · Cited by 133 · 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
Self-citationZhang, J., Fang, F., Liu, B., Tan, J., Chen, W., Zhu, Z., Yuan, Y., Wan, Y., Cui, X., Li, S., et al. (2019) · ACS Applied Materials & Interfaces · doi:10.1021/acsami.9b14552 · Cited by 105 · 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
Luo, M., Li, X., Ding, L., Baryshnikov, G., Shen, S., Zhu, M., Zhou, L., Zhang, M., Lu, J., Ågren, H., et al. (2020) · Angewandte Chemie International Edition · doi:10.1002/anie.202009077 · Cited by 89 · see citing works
Thermally activated delayed fluorescence molecules and their new applications aside from OLEDs
Chen, W., & Song, F. (2019) · Chinese Chemical Letters · doi:10.1016/j.cclet.2019.08.032 · Cited by 77 · 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
Self-citationPaisley, N. R., Tonge, C. M., & Hudson, Z. M. (2020) · Frontiers in Chemistry · doi:10.3389/fchem.2020.00229 · Cited by 67 · see citing works
Li, X., Baryshnikov, G., Ding, L., Bao, X., Li, X., Lu, J., Liu, M., Shen, S., Luo, M., Zhang, M., et al. (2020) · Angewandte Chemie International Edition · doi:10.1002/anie.202000185 · Cited by 61 · see citing works
Zhao, B., Xie, G., Wang, H., Han, C., & Xu, H. (2018) · Chemistry - A European Journal · doi:10.1002/chem.201805201 · Cited by 50 · see citing works
Self-citationXiong, X., Zheng, L., Yan, J., Ye, F., Qian, Y., & Song, F. (2015) · RSC Advances · doi:10.1039/c5ra08539j · Cited by 40 · 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
Thermally activated delayed fluorescence organic dots for two-photon fluorescence lifetime imaging
He, T., Ren, C., Li, Z., Xiao, S., Li, J., Lin, X., Ye, C., Zhang, J., Guo, L., Hu, W., et al. (2018) · Applied Physics Letters · doi:10.1063/1.5034375 · Cited by 33 · see citing works
Aggregation‐Induced Delayed Fluorescence
Liu, H., Guo, J., Zhao, Z., & Tang, B. Z. (2019) · ChemPhotoChem · doi:10.1002/cptc.201900118 · Cited by 32 · see citing works
TADF Dye-Loaded Nanoparticles for Fluorescence Live-Cell Imaging
Crucho, C. I. C., Avó, J., Diniz, A. M., Pinto, S. N., Barbosa, J., Smith, P. O., Berberan-Santos, M. N., Pålsson, L., & Dias, F. B. (2020) · Frontiers in Chemistry · doi:10.3389/fchem.2020.00404 · Cited by 31 · 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
Silica nanoparticles with thermally activated delayed fluorescence for live cell imaging
Crucho, C. I. C., Avó, J., Nobuyasu, R. S., Pinto, S. N., Fernandes, F., Lima, J. C., Berberan-Santos, M. N., & Dias, F. B. (2019) · Materials Science and Engineering C · doi:10.1016/j.msec.2019.110528 · 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
Zhu, Z., & Shu, X. (2018) · Sensors and Actuators B Chemical · doi:10.1016/j.snb.2018.10.071 · Cited by 15 · see citing works
Flagged first, then by citations
Research works printed but not linked: 38
- H. Kobayashi, M. Ogawa, R. Alford, P. L. Choyke, Y. Urano, Chem. Rev. 2010, 110, 2620.
- Y. Yang, Q. Zhao, W. Feng, F. Li, Chem. Rev. 2013, 113, 192.
- A. S. Stender, K. Marchuk, C. Liu, S. Sander, M. W. Meyer, E. A. Smith, B. Neupane, G. Wang, J. Li, J.-X. Cheng, B. Huang, N. Fang, Chem. Rev. 2013, 113, 2469.
- K. Y. Zhang, Q. Yu, H. Wei, S. Liu, Q. Zhao, W. Huang, Chem. Rev. 2018, 118, 1770.
- M. Y. Berezin, S. Achilefu, Chem. Rev. 2010, 110, 2641.
- X. Xiong, F. Song, J. Wang, Y. Zhang, Y. Xue, L. Sun, N. Jiang, P. Gao, L. Tian, X. Peng, J. Am. Chem. Soc. 2014, 136, 9590.
- F. Ni, N. Li, L. Zhan, C. Yang, Adv. Opt. Mater. 2020, 8, 1902187.
- H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Nature 2012, 492, 234.
- Z. Yang, Z. Mao, Z. Xie, Y. Zhang, S. Liu, J. Zhao, J. Xu, Z. Chi, M. P. Aldred, Chem. Soc. Rev. 2017, 46, 915.
- B. Zhao, H. Wang, C. Han, P. Ma, Z. Li, P. Chang, H. Xu, Angew. Chem., Int. Ed. 2020, 59, 19042.
- W. Chen, F. Song, Chin. Chem. Lett. 2019, 30, 1717.
- N. R. Paisley, C. M. Tonge, Z. M. Hudson, Front. Chem. 2020, 8, 229.
- J. Zhang, W. Chen, S. Kalytchuk, K. F. Li, R. Chen, C. Adachi, Z. Chen, A. L. Rogach, G. Zhu, P. K. N. Yu, W. Zhang, K. W. Cheah, X. Zhang, C.-S. Lee, ACS Appl. Mater. Interfaces 2016, 8, 11355.
- Z. Zhu, X. Shu, Sens. Actuators, B 2019, 280, 177.
- C. I. C. Crucho, J. Avo, A. M. Diniz, S. N. Pinto, J. Barbosa, P. O. Smith, M. N. Berberan-Santos, L.-O. Palsson, F. B. Dias, Front. Chem. 2020, 8, 404.
- C. I. C. Crucho, J. Avo, R. Nobuyasu, S. N. Pinto, F. Fernandes, J. C. Lima, M. N. Berberan-Santos, F. B. Dias, Mater. Sci. Eng., C 2020, 109, 110528.
- J. Zhang, F. Fang, B. Liu, J.-H. Tan, W.-C. Chen, Z. Zhu, Y. Yuan, Y. Wan, X. Cui, S. Li, Q.-X. Tong, J. Zhao, X.-M. Meng, C.-S. Lee, ACS Appl. Mater. Interfaces 2019, 11, 41051.
- X. Xiong, L. Zheng, J. Yan, F. Ye, Y. Qian, F. Song, RSC Adv. 2015, 5, 53660.
- Y. Wu, F. Song, W. Luo, Z. Liu, B. Song, X. Peng, Chemphotochem 2017, 1, 79.
- T. He, C. Ren, Z. Li, S. Xiao, J. Li, X. Lin, C. Ye, J. Zhang, L. Guo, W. Hu, R. Chen, Appl. Phys. Lett. 2018, 112, 211102.
- Z. Zhu, D. Tian, P. Gao, K. Wang, Y. Li, X. Shu, J. Zhu, Q. Zhao, J. Am. Chem. Soc. 2018, 140, 17484.
- X. Li, G. Baryshnikov, C. Deng, X. Bao, B. Wu, Y. Zhou, H. Agren, L. Zhu, Nat. Commun. 2019, 10, 731.
- Y. Wu, L. Jiao, F. Song, M. Chen, D. Liu, W. Yang, Y. Sun, G. Hong, L. Liu, X. Peng, Chem. Commun. 2019, 55, 14522.
- X. Li, G. Baryshnikov, L. Ding, X. Bao, X. Li, J. Lu, M. Liu, S. Shen, M. Luo, M. Zhang, H. Agren, X. Wang, L. Zhu, Angew. Chem., Int. Ed. 2020, 59, 7548.
- R. Wei, L. Zhang, S. Xu, Q. Zhang, Y. Qi, H.-Y. Hu, Chem. Commun. 2020, 56, 2550.
- J. Guo, X.-L. Li, H. Nie, W. Luo, S. Gan, S. Hu, R. Hu, A. Qin, Z. Zhao, S.-J. Su, B. Z. Tang, Adv. Funct. Mater. 2017, 27, 1606458.
- J. Huang, H. Nie, J. Zeng, Z. Zhuang, S. Gan, Y. Cai, J. Guo, S.-J. Su, Z. Zhao, B. Z. Tang, Angew. Chem., Int. Ed. 2017, 56, 12971.
- H. Liu, J. Guo, Z. Zhao, B. Z. Tang, ChemPhotoChem 2019, 3, 993.
- J. Zhang, R. Chen, Z. Zhu, C. Adachi, X. Zhang, C.-S. Lee, ACS Appl. Mater. Interfaces 2015, 7, 26266.
- T. Li, D. Yang, L. Zhai, S. Wang, B. Zhao, N. Fu, L. Wang, Y. Tao, W. Huang, Adv. Sci. 2017, 4, 1600166.
- S. Gan, J. Zhou, T. A. Smith, H. Su, W. Luo, Y. Hong, Z. Zhao, B. Z. Tang, Mater. Chem. Front. 2017, 1, 2554.
- W. Hu, L. Guo, L. Bai, X. Miao, Y. Ni, Q. Wang, H. Zhao, M. Xie, L. Li, X. Lu, W. Huang, Q. Fan, Adv. Healthcare Mater. 2018, 7, 1800299.
- S. K. Sarkar, M. Pegu, S. K. Behera, S. K. Narra, P. Thilagar, Chem. Asian J. 2019, 14, 4588.
- M. Luo, X. Li, L. Ding, G. Baryshnikov, S. Shen, M. Zhu, L. Zhou, M. Zhang, J. Lu, H. Ågren, X.-d. Wang, L. Zhu, Angew. Chem., Int. Ed. 2020, 59, 17018.
- F. Ni, Z. Zhu, X. Tong, M. Xie, Q. Zhao, C. Zhong, Y. Zou, C. Yang, Chem. Sci. 2018, 9, 6150.
- F. Ni, Z. Zhu, X. Tong, W. Zeng, K. An, D. Wei, S. Gong, Q. Zhao, X. Zhou, C. Yang, Adv. Sci. 2019, 6, 1801729.
- Q. Zhang, S. Xu, M. Li, Y. Wang, N. Zhang, Y. Guan, M. Chen, C.-F. Chen, H.-Y. Hu, Chem. Commun. 2019, 55, 5639.
- B. Zhao, G. Xie, H. Wang, C. Han, H. Xu, Chemistry 2019, 25, 1010.
Cited by
Sorted by citations
The Golden Age of Thermally Activated Delayed Fluorescence Materials: Design and Exploitation
dos Santos, J. M., Hall, D., Basumatary, B., Bryden, M. A., Chen, D., Choudhary, P., Comerford, T. A., Crovini, E., Danos, A., De, J., et al. (2024) · Chemical Reviews · doi:10.1021/acs.chemrev.3c00755 · Cited by 498 · see citing works
Barman, D., Narang, K., Parui, R., Zehra, N., Khatun, M. N., Adil, L. R., & Iyer, P. K. (2022) · Aggregate · doi:10.1002/agt2.172 · Cited by 113 · see citing works
Huo, M., Dai, X., & Liu, Y. (2021) · Small · doi:10.1002/smll.202104514 · Cited by 58 · see citing works
Kim, T., Shin, G., Park, T., & Kim, M. (2024) · Advanced Functional Materials · doi:10.1002/adfm.202412267 · Cited by 46 · see citing works
Red Multi‐Resonant Thermally Activated Delayed Fluorescence Emitters as Bioimaging Agents
Si, C., Primrose, W. L., Xu, Y., Hudson, Z. M., & Zysman‐Colman, E. (2024) · Advanced Optical Materials · doi:10.1002/adom.202402576 · Cited by 30 · see citing works
Ni, F., Xie, M., Liu, T., Zhou, X. M., Chen, Z., Zheng, K., Wu, Y., Zhao, Q., & Yang, C. (2022) · Chemical Engineering Journal · doi:10.1016/j.cej.2022.135396 · Cited by 23 · see citing works
Self-citationChu, Y., Jin, X., Ji, G., Li, P., Xiao, S., Wang, W., & Song, Z. (2025) · ACS Nano · doi:10.1021/acsnano.4c11719 · Cited by 17 · see citing works
Cucurbit[8]uril-based supramolecular theranostics
Wu, D. Q., Wang, J., Du, X., Cao, Y., Ping, K., & Liu, D. (2024) · Journal of Nanobiotechnology · doi:10.1186/s12951-024-02349-z · Cited by 13 · see citing works
Barnwal, N., Sarkar, P., Nandi, N., & Sahu, K. (2025) · ACS Applied Nano Materials · doi:10.1021/acsanm.5c02556 · Cited by 11 · see citing works
Photo- and electro-luminescence properties of two coumarin-triarylimidazole hybrid derivatives
Wu, X., Su, R., Zhao, Y., Ma, H., Liu, X., Qian, L., Han, M., Su, W., & Yu, T. (2021) · New Journal of Chemistry · doi:10.1039/d1nj04676d · Cited by 6 · see citing works
Anand, A., Perinbanathan, S., Gokul, A. S., Goud, E. V., Ranjan, P., Desikan, R., Rao, C. V. S. B., & Sivaramakrishna, A. (2025) · Journal of Molecular Liquids · doi:10.1016/j.molliq.2025.128625 · Cited by 1 · see citing works
External Heavy Atom Effects Accelerate Intersystem Crossing in Glassy Organic Dots
Elgadi, S. A., Mikulin, S., Hu, P., & Hudson, Z. M. (2026) · ACS Applied Nano Materials · doi:10.1021/acsanm.6c00445 · Cited by 1 · see citing works
- Authors
- Zhao, B., Wang, H., Xie, M., Han, C., Yang, H., Zhao, W., Zhao, Q., & Xu, H.
- Affiliations
- Heilongjiang University (CN)
- Nanjing University of Posts and Telecommunications (CN)
- Corresponding author
- Han, Chunmiao
- Zhao, Qiang
- Xu, Hui
- Venue
- Advanced Photonics Research
- Publisher
- Wiley
- Published
- 2020-12-27
- Volume
- 2
- Issue
- 2
- ISSN
- 2699-9293 (ISSN-L)
- OpenAlex
- W3109703521
- Cited by
- 12
- References
- 38
- Citations by year
- 2026: 1 · 2025: 3 · 2024: 4 · 2022: 2 · 2021: 2
- FWCI
- 0.39
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Licence
- Locations
- Advanced Photonics Research (publishedVersion, cc-by)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion)
- Funders
- National Natural Science Foundation of China (21672056, 21602048, 51873056)
- 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 › Spectroscopy › Molecular Sensors and Ion Detection
- Keywords
- phosphine oxides, thermally activated delayed fluorescence, carbazole, diphenylphosphine oxide, steric hindrance, intermolecular hydrogen bonding, dimerization, emission lifetime, cell imaging
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
