Thermally Activated Delayed Fluorescence of Fluorescein Derivative for Time-Resolved and Confocal Fluorescence Imaging
Abstract
Compared with fluorescence imaging utilizing fluorophores whose lifetimes are in the order of nanoseconds, time-resolved fluorescence microscopy has more advantages in monitoring target fluorescence. In this work, compound DCF-MPYM, which is based on a fluorescein derivative, showed long-lived luminescence (22.11 μs in deaerated ethanol) and was used in time-resolved fluorescence imaging in living cells. Both nanosecond time-resolved transient difference absorption spectra and time-correlated single-photon counting (TCSPC) were employed to explain the long lifetime of the compound, which is rare in pure organic fluorophores without rare earth metals and heavy atoms. A mechanism of thermally activated delayed fluorescence (TADF) that considers the long wavelength fluorescence, large Stokes shift, and long-lived triplet state of DCF-MPYM was proposed. The energy gap (ΔEST) of DCF-MPYM between the singlet and triplet state was determined to be 28.36 meV by the decay rate of DF as a function of temperature. The ΔE(ST) was small enough to allow efficient intersystem crossing (ISC) and reverse ISC, leading to efficient TADF at room temperature. The straightforward synthesis of DCF-MPYM and wide availability of its starting materials contribute to the excellent potential of the compound to replace luminescent lanthanide complexes in future time-resolved imaging technologies.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
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
Photosensitized singlet oxygen and its applications
DeRosa, M. C. (2002) · Coordination Chemistry Reviews · doi:10.1016/s0010-8545(02)00034-6 · Cited by 2,964 · see citing works
Goushi, K., Yoshida, K., Sato, K., & Adachi, C. (2012) · Nature Photonics · doi:10.1038/nphoton.2012.31 · Cited by 1,705 · see citing works
Activating efficient phosphorescence from purely organic materials by crystal design
Bolton, O., Lee, K., Kim, H.-J., Lin, K. Y., & Kim, J. (2011) · Nature Chemistry · doi:10.1038/nchem.984 · Cited by 1,662 · 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
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
Phosphorescent chemosensors based on heavy-metal complexes
Zhao, Q., Li, F., & Huang, C. (2010) · Chemical Society Reviews · doi:10.1039/b915340c · Cited by 1,249 · see citing works
A dual-emissive-materials design concept enables tumour hypoxia imaging
Zhang, G., Palmer, G. M., Dewhirst, M. W., & Fraser, C. L. (2009) · Nature Materials · doi:10.1038/nmat2509 · Cited by 1,151 · see citing works
A Compilation of Singlet Oxygen Yields from Biologically Relevant Molecules
Redmond, R. W., & Gamlin, J. N. (1999) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1999.tb08240.x · Cited by 1,142 · see citing works
Endo, A., Ogasawara, M., Takahashi, A., Yokoyama, D., Kato, Y., & Adachi, C. (2009) · Advanced Materials · doi:10.1002/adma.200900983 · Cited by 985 · see citing works
In Vitro Demonstration of the Heavy-Atom Effect for Photodynamic Therapy
Gorman, A., KILLORAN, J. J., O'Shea, C., Kenna, T., Gallagher, W. M., & O’Shea, D. F. (2004) · Journal of the American Chemical Society · doi:10.1021/ja047649e · Cited by 920 · see citing works
Zhang, G., Chen, J., Payne, S. J., Kooi, S. E., Demas, J. N., & Fraser, C. L. (2007) · Journal of the American Chemical Society · doi:10.1021/ja0720255 · Cited by 619 · see citing works
Méhes, G., Nomura, H., Zhang, Q., Nakagawa, T., & Adachi, C. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201206289 · Cited by 586 · see citing works
Room Temperature Phosphorescence of Metal-Free Organic Materials in Amorphous Polymer Matrices
Lee, D., Bolton, O., Kim, B. C., Youk, J. H., Takayama, S., & Kim, J. (2013) · Journal of the American Chemical Society · doi:10.1021/ja401769g · Cited by 569 · see citing works
Solvent Dependence of the Fluorescence Lifetimes of Xanthene Dyes
Magde, D., Rojas, G. E., & Seybold, P. G. (1999) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1999.tb08277.x · Cited by 513 · see citing works
Deaton, J. C., Switalski, S. C., Kondakov, D. Y., Young, R. H., Pawlik, T. D., Giesen, D. J., Harkins, S. B., Miller, A. J. M., Mickenberg, S. F., & Peters, J. C. (2010) · Journal of the American Chemical Society · doi:10.1021/ja1004575 · Cited by 500 · see citing works
Chlorophyll a Fluorescence in Aquatic Sciences: Methods and Applications
Suggett, D. J., Prášil, O., & Borowitzka, M. A. (2010) · Springer eBooks · doi:10.1007/978-90-481-9268-7 · Cited by 486 · see citing works
Nakagawa, T., Ku, S.-Y., Wong, K., & Adachi, C. (2012) · Chemical Communications · doi:10.1039/c2cc31468a · Cited by 456 · see citing works
Peng, X., Yang, Z., Wang, J., et al. (2011) · Journal of the American Chemical Society · doi:10.1021/ja1104014 · Cited by 430 · see citing works
Self-citationActivation of Endogenous Cdc42 Visualized in Living Cells
Nalbant, P., Hodgson, L., Kraynov, V. S., Toutchkine, A., & Hahn, K. M. (2004) · Science · doi:10.1126/science.1100367 · Cited by 391 · see citing works
A Europium(III) Complex as an Efficient Singlet Oxygen Luminescence Probe
Song, B., Wang, G., Tan, M., & Yuan, J. (2006) · Journal of the American Chemical Society · doi:10.1021/ja062990f · Cited by 364 · see citing works
Tanaka, H., Shizu, K., Nakanotani, H., & Adachi, C. (2013) · Chemistry of Materials · doi:10.1021/cm402428a · Cited by 334 · see citing works
Lee, J., Shizu, K., Tanaka, H., Nomura, H., Yasuda, T., & Adachi, C. (2013) · Journal of Materials Chemistry C · doi:10.1039/c3tc30699b · Cited by 330 · see citing works
In vivo time-gated fluorescence imaging with biodegradable luminescent porous silicon nanoparticles
Gu, L., Hall, D. J., Qin, Z., Anglin, E. J., Joo, J., Mooney, D. J., Howell, S. B., & Sailor, M. J. (2013) · Nature Communications · doi:10.1038/ncomms3326 · Cited by 329 · see citing works
Liu, Q., Yin, B., Yang, T., Yang, Y., Shen, Z., Yao, P., & Li, F. (2013) · Journal of the American Chemical Society · doi:10.1021/ja3104268 · Cited by 297 · see citing works
Weibel, N., Charbonnière, L. J., Guardigli, M., Roda, A., & Ziessel, R. F. (2004) · Journal of the American Chemical Society · doi:10.1021/ja031886k · Cited by 285 · see citing works
Hanaoka, K., Kikuchi, K., Kobayashi, S., & Nagano, T. (2007) · Journal of the American Chemical Society · doi:10.1021/ja073392j · Cited by 262 · see citing works
Zhang, C., Zhao, J., Wu, S., Wang, Z., Wu, W., Ma, J., Guo, S., & Huang, L. F. (2013) · Journal of the American Chemical Society · doi:10.1021/ja405170j · Cited by 241 · see citing works
Nasu, K., Nakagawa, T., Nomura, H., Lin, C.-J., Cheng, C., Tseng, M., Yasuda, T., & Adachi, C. (2013) · Chemical Communications · doi:10.1039/c3cc44179b · Cited by 225 · see citing works
Unusually Strong Delayed Fluorescence of C 70
Berberan-Santos, M. N., & Garcia, J. M. M. (1996) · Journal of the American Chemical Society · doi:10.1021/ja961782s · Cited by 216 · see citing works
Solvent Dependence of the Ultrafast S2−S1 Internal Conversion Rate of β-Carotene
Macpherson, A. N., & Gillbro, T. (1998) · The Journal of Physical Chemistry A · doi:10.1021/jp980979z · Cited by 200 · see citing works
Lanthanide Complex-Based Fluorescence Label for Time-Resolved Fluorescence Bioassay
Yuan, J., & Wang, G. (2005) · Journal of Fluorescence · doi:10.1007/s10895-005-2829-3 · Cited by 173 · see citing works
Takase, M., Narita, T., Fujita, W., Asano, M. S., Nishinaga, T., Benten, H., Yoza, K., & Müllen, K. (2013) · Journal of the American Chemical Society · doi:10.1021/ja402371f · Cited by 159 · see citing works
In Vivo Mitochondrial Oxygen Tension Measured by a Delayed Fluorescence Lifetime Technique
Mik, E. G., Johannes, T., Zuurbier, C. J., et al. (2008) · Biophysical Journal · doi:10.1529/biophysj.107.126094 · Cited by 136 · see citing works
Fluorescence Dynamics in BSA-Protected Au25Nanoclusters
Wen, X., Yu, P., Toh, Y., et al. (2012) · The Journal of Physical Chemistry C · doi:10.1021/jp305902w · Cited by 135 · see citing works
Yao, L., Yang, B., & Ma, Y. (2014) · Science China Chemistry · doi:10.1007/s11426-013-5046-y · Cited by 133 · see citing works
Xiao, Y., Zhang, R., Ye, Z., Dai, Z., An, H., & Yuan, J. (2012) · Analytical Chemistry · doi:10.1021/ac3028189 · Cited by 132 · see citing works
Zhang, S., Wu, T., Fan, J., et al. (2012) · Organic & Biomolecular Chemistry · doi:10.1039/c2ob26911b · Cited by 121 · see citing works
Yang, P., Zhao, J., Wu, W., Yu, X., & Liu, Y. (2012) · The Journal of Organic Chemistry · doi:10.1021/jo300943t · Cited by 121 · see citing works
Tang, Y. B., Yang, H., Sun, H., Liu, S., Wang, J., Zhao, Q., Liu, X., Xu, W., Li, S., & Huang, W. (2012) · Chemistry - A European Journal · doi:10.1002/chem.201203137 · Cited by 112 · see citing works
Self-citationA new europium chelate-based phosphorescence probe specific for singlet oxygen
Song, B., Wang, G., & Yuan, J. (2005) · Chemical Communications · doi:10.1039/b503980k · Cited by 99 · see citing works
Ye, Z., Tan, M., Wang, G., et al. (2004) · Journal of Materials Chemistry · doi:10.1039/b311905j · Cited by 95 · see citing works
Li, C., Liu, Y., Wu, Y., Sun, Y., & Li, F. (2012) · Biomaterials · doi:10.1016/j.biomaterials.2012.09.014 · Cited by 76 · see citing works
Li, Z., Sun, S., Yang, Z., et al. (2013) · Biomaterials · doi:10.1016/j.biomaterials.2013.05.020 · Cited by 76 · see citing works
Ogunsipe, A. O., & Nyokong, T. (2005) · Photochemical & Photobiological Sciences · doi:10.1039/b416304d · Cited by 75 · see citing works
Construction of Long‐Wavelength Fluorescein Analogues and Their Application as Fluorescent Probes
Xiong, X., Song, F., Chen, G., Sun, W. C., Wang, J., Gao, P., Zhang, Y., Qiao, B., Li, W., Sun, S., et al. (2013) · Chemistry - A European Journal · doi:10.1002/chem.201300418 · Cited by 73 · see citing works
Self-citationDevelopment of a ratiometric time-resolved luminescence sensor for pH based on lanthanide complexes
Liu, M., Ye, Z., Xin, C., et al. (2012) · Analytica Chimica Acta · doi:10.1016/j.aca.2012.11.025 · Cited by 71 · see citing works
A cell-membrane-permeable europium complex as an efficient luminescent probe for singlet oxygen
Dai, Z., Tian, L., Xiao, Y., Ye, Z., Zhang, R., & Yuan, J. (2013) · Journal of Materials Chemistry B · doi:10.1039/c2tb00350c · Cited by 68 · see citing works
Self-citationCui, X., Charaf-Eddin, A., Wang, J., et al. (2014) · The Journal of Organic Chemistry · doi:10.1021/jo402718e · Cited by 56 · see citing works
Self-citationColorimetric sensing of cyanide anion in aqueous media with a fluorescein–spiropyran conjugate
Sumiya, S., Doi, T., Shiraishi, Y., et al. (2011) · Tetrahedron · doi:10.1016/j.tet.2011.10.097 · Cited by 54 · see citing works
Singlet oxygen-sensitized delayed fluorescence of common water-soluble photosensitizers
Scholz, M., Dĕdic, R., Breitenbach, T., et al. (2013) · Photochemical & Photobiological Sciences · doi:10.1039/c3pp50170a · Cited by 52 · see citing works
Direct Observation of Delayed Fluorescence from a Remarkable Back-Isomerization in Cy5
Huang, Z., Ji, D., Xia, A., et al. (2005) · Journal of the American Chemical Society · doi:10.1021/ja050050+ · Cited by 48 · see citing works
Kobayashi, A., Takehira, K., Yoshihara, T., et al. (2012) · Photochemical & Photobiological Sciences · doi:10.1039/c2pp25055a · Cited by 38 · see citing works
Tian, L., Dai, Z., Zhang, L., Zhang, R., Ye, Z., Wu, J., Jin, D., & Yuan, J. (2012) · Nanoscale · doi:10.1039/c2nr30233k · Cited by 37 · see citing works
Self-citationRed‐Emissive Fluorescein Derivatives and Detection of Bovine Serum Albumin
Xiong, X., Song, F., Sun, S., et al. (2013) · Asian Journal of Organic Chemistry · doi:10.1002/ajoc.201200109 · Cited by 37 · see citing works
Self-citationNon-protected fluid room temperature phosphorescence of several naphthalene derivatives
Li, L.-D., Zhao, Y., Wu, Y., et al. (1998) · Talanta · doi:10.1016/s0039-9140(97)00378-0 · Cited by 36 · see citing works
Time-Resolved Thermally Activated Delayed Fluorescence in C70 and 1,2-C70H2
Bachilo, S. M., Benedetto, A. F., Weisman, R. B., et al. (2000) · The Journal of Physical Chemistry A · doi:10.1021/jp002742k · Cited by 33 · see citing works
Optical imaging through scattering media via magnetically modulated fluorescence
Yang, N., & Cohen, A. E. (2010) · Optics Express · doi:10.1364/oe.18.025461 · Cited by 29 · see citing works
Guo, H., Li, Q., Ma, L., et al. (2012) · Journal of Materials Chemistry · doi:10.1039/c2jm32074f · Cited by 28 · see citing works
Quenching of Triplet State Fluorophores for Studying Diffusion-Mediated Reactions in Lipid Membranes
Strömqvist, J., Chmyrov, A., Johansson, S., Andersson, A., Mäler, L., & Widengren, J. (2010) · Biophysical Journal · doi:10.1016/j.bpj.2010.09.059 · Cited by 26 · see citing works
Lee, W.-K., & Galley, W. C. (1988) · Biophysical Journal · doi:10.1016/s0006-3495(88)82998-9 · Cited by 20 · see citing works
Photophysics of 1-dimethylaminonaphthalene in aqueous-organic binary solvents
Chen, H., & Jiang, Y. (2000) · Chemical Physics Letters · doi:10.1016/s0009-2614(00)00741-7 · Cited by 18 · see citing works
Benniston, A. C., Harriman, A., Llarena, I., et al. (2007) · Chemistry of Materials · doi:10.1021/cm062525h · Cited by 16 · see citing works
Zrimec, M. B., Drinovec, L., & Zrimec, A. (2010) · Springer eBooks · doi:10.1007/978-90-481-9268-7_14 · Cited by 11 · see citing works
Difference between Prompt and Delayed Fluorescence Spectra
Grzywacz, J. (1967) · Nature · doi:10.1038/213385a0 · Cited by 10 · see citing works
Triplet Imaging of Oxygen Consumption During the Contraction of a Single Smooth Muscle Cell (A7r5)
Geissbuehler, M., Spielmann, T., Formey, A., et al. (2011) · Advances in experimental medicine and biology · doi:10.1007/978-1-4614-1566-4_39 · Cited by 1 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
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
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
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
Qi, S., Kim, S., Nguyen, V.-N., Kim, Y., Niu, G., Kim, G., Kim, S.-J., Park, S., & Yoon, J. (2020) · ACS Applied Materials & Interfaces · doi:10.1021/acsami.0c15936 · Cited by 112 · 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
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
Phosphine Oxides Manipulate Aggregation‐Induced Delayed Fluorescence for Time‐Resolved Bioimaging
Zhao, B., Wang, H., Xie, M., Han, C., Yang, H., Zhao, W., Zhao, Q., & Xu, H. (2021) · Advanced Photonics Research · doi:10.1002/adpr.202000096 · Cited by 12 · see citing works
- Authors
- Xiong, X., Song, F., Wang, J., Zhang, Y., Xue, Y., Sun, L., Jiang, N., Gao, P., Tian, L., & Peng, X.
- Affiliations
- Dalian University of Technology (CN)
- Corresponding author
- Song, Fengling
- ORCID
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2014-06-26
- Volume
- 136
- Issue
- 27
- Pages
- 9590-9597
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2319458912
- Cited by
- 326
- References
- 66
- Citations by year
- 2026: 7 · 2025: 21 · 2024: 29 · 2023: 25 · 2022: 32 · 2021: 40 · 2020: 40 · 2019: 41 · 2018: 35 · 2017: 20 · 2016: 19 · 2015: 12 · 2014: 5
- FWCI
- 8.47
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Ministry of Education of the People's Republic of China
- National Natural Science Foundation of China (21006009, 21136002, 21222605, 21376039)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
- Physical Sciences › Engineering › Electrical and Electronic Engineering › Organic Light-Emitting Diodes Research
- Keywords
- thermally activated delayed fluorescence, fluorescein derivatives, time-resolved fluorescence imaging, confocal fluorescence imaging, long-lived luminescence, triplet state, band gap, intersystem crossing, reverse intersystem crossing, Stokes shift, time-correlated single photon counting, live-cell imaging
- MeSH terms
- Fluorescence, Microscopy, Fluorescence, Temperature, Time Factors, Molecular Structure, Microscopy, Confocal, Fluorescein, Molecular 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
