A structural remedy toward bright dipolar fluorophores in aqueous media
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Structural factors governing the poor emission of dipolar dyes in aqueous media are identified, leading to new acedan derivatives with brighter fluorescence and enhanced two-photon properties.
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A hydrogen-bond-assisted excited-state nonradiative deactivation pathway often predominates in dyes with an intramolecular charge transfer character.
“A hydrogen-bond-assisted excited-state nonradiative deactivation pathway often predominates in dyes with an ICT character.77−79”
From The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates (2022) · cites this paper as [79]
In “Our rationale,” the authors propose that hydrogen bonding with water provides a major nonradiative deactivation pathway for dipolar fluorophores in water. But the claim extends that aqueous-medium proposal to ICT dyes generally. In “Photophysical properties of acedan and its derivatives,” the authors also say allylic strain seems to play the major role in the emission behavior they studied. (LLM, conf=0.87)
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Cites
Principles of Fluorescence Spectroscopy
Lakowicz, J. R. (1999) · Springer eBooks · doi:10.1007/978-1-4757-3061-6 · Cited by 26,948 · see citing works
Nonlinear magic: multiphoton microscopy in the biosciences
Zipfel, W. R., Williams, R. M., & Webb, W. W. (2003) · Nature Biotechnology · doi:10.1038/nbt899 · Cited by 3,911 · see citing works
Grabowski, Z. R., Rotkiewicz, K., & Rettig, W. (2003) · Chemical Reviews · doi:10.1021/cr940745l · Cited by 3,714 · see citing works
Fluorescent and colorimetric probes for detection of thiols
Chen, X., Zhou, Y., Peng, X., & Yoon, J. (2010) · Chemical Society Reviews · doi:10.1039/b925092a · Cited by 1,580 · see citing works
A general method to improve fluorophores for live-cell and single-molecule microscopy
Grimm, J. B., English, B. P., Chen, J., Slaughter, J. P., Zhang, Z., Revyakin, A. G., Patel, R. H., Macklin, J. J., Normanno, D., Singer, R. H., et al. (2015) · Nature Methods · doi:10.1038/nmeth.3256 · Cited by 1,509 · see citing works
Allylic 1,3-strain as a controlling factor in stereoselective transformations
Hoffmann, R. W. (1989) · Chemical Reviews · doi:10.1021/cr00098a009 · Cited by 1,257 · see citing works
Macro-/micro-environment-sensitive chemosensing and biological imaging
Yang, Z., Cao, J., He, Y., Yang, J. H., Kim, T. Y., Peng, X., & Kim, J. S. (2014) · Chemical Society Reviews · doi:10.1039/c4cs00051j · Cited by 877 · see citing works
Self-citationWeber, G., & Farris, F. J. (1979) · Biochemistry · doi:10.1021/bi00581a025 · Cited by 857 · see citing works
Visualizing lipid structure and raft domains in living cells with two-photon microscopy
Gaus, K., Gratton, E., Kable, E., Jones, A. S., Gelissen, I. C., Kritharides, L., & Jessup, W. (2003) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.2534386100 · Cited by 526 · see citing works
Fluorescent Probes for Lipid Rafts: From Model Membranes to Living Cells
Klymchenko, A. S., & Kreder, R. (2013) · Chemistry & Biology · doi:10.1016/j.chembiol.2013.11.009 · Cited by 516 · see citing works
Yu, H., Xiao, Y., & Jin, L. (2012) · Journal of the American Chemical Society · doi:10.1021/ja308967u · Cited by 445 · see citing works
Probing Protein Electrostatics with a Synthetic Fluorescent Amino Acid
Cohen, B. E., McAnaney, T. B., Park, E.-S., et al. (2002) · Science · doi:10.1126/science.1069346 · Cited by 381 · see citing works
Two-Photon Microscopy of Cells and Tissue
Rubart, M. (2004) · Circulation Research · doi:10.1161/01.res.0000150593.30324.42 · Cited by 341 · see citing works
A Two-Photon Fluorescent Probe for Thiols in Live Cells and Tissues
Lee, J. H., Lim, C. S., Tian, Y. S., et al. (2010) · Journal of the American Chemical Society · doi:10.1021/ja9090676 · Cited by 314 · see citing works
Monitoring protein interactions and dynamics with solvatochromic fluorophores
Loving, G. S., Sainlos, M., & Imperiali, B. (2009) · Trends in biotechnology · doi:10.1016/j.tibtech.2009.11.002 · Cited by 305 · see citing works
Estimation of the polarity of the protein interior by optical spectroscopy
Macgregor, R. B., & Weber, G. (1986) · Nature · doi:10.1038/319070a0 · Cited by 262 · see citing works
Two‐Photon Fluorescent Probes for Bioimaging
Yao, S., & Belfield, K. D. (2012) · European Journal of Organic Chemistry · doi:10.1002/ejoc.201200281 · Cited by 261 · see citing works
Lee, H. S., Guo, J., Lemke, E. A., Dimla, R. D., & Schultz, P. G. (2009) · Journal of the American Chemical Society · doi:10.1021/ja904896s · Cited by 226 · see citing works
Controlling the Structures and Photonic Properties of Organic Nanomaterials by Molecular Design
Yao, W. F., Yan, Y., Lin, X., Zhang, C., Li, G., Zheng, Q., Zhao, Y. S., Jiang, H., & Yao, J. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201302894 · Cited by 214 · see citing works
Li, L., Zhang, C., Chen, G. Y. J., Zhu, B., Chai, C., Xu, Q., Tan, E., Zhu, Q. X., Lim, K., & Yao, S. Q. (2014) · Nature Communications · doi:10.1038/ncomms4276 · Cited by 203 · see citing works
Recent development of two-photon fluorescent probes for bioimaging
Kim, D., Ryu, H. G., & Ahn, K. H. (2014) · Organic & Biomolecular Chemistry · doi:10.1039/c4ob00431k · Cited by 192 · see citing works
Self-citationVogel, M., Rettig, W., Sens, R., & Drexhage, K. H. (1988) · Chemical Physics Letters · doi:10.1016/0009-2614(88)85007-3 · Cited by 177 · see citing works
Metal-Ion-Responsive Fluorescent Probes for Two-Photon Excitation Microscopy
Sumalekshmy, S., & Fahrni, C. J. (2010) · Chemistry of Materials · doi:10.1021/cm1021905 · Cited by 170 · see citing works
Benedetti, E., Kocsis, L. S., & Brummond, K. M. (2012) · Journal of the American Chemical Society · doi:10.1021/ja3055029 · Cited by 140 · see citing works
Two-Photon Fluorescent Turn-On Probe for Lipid Rafts in Live Cell and Tissue
Kim, H. M., Jeong, B. H., Hyon, J., et al. (2008) · Journal of the American Chemical Society · doi:10.1021/ja711391f · Cited by 133 · see citing works
A turn-on two-photon fluorescent probe for ATP and ADP
Rao, A. S., Kim, D., Nam, H., Jo, H., Kim, K. H., Ban, C., & Ahn, K. H. (2012) · Chemical Communications · doi:10.1039/c2cc17629g · Cited by 132 · see citing works
Self-citationTwo‐Photon Fluorescent Probes for Metal Ions
Kim, H. M., & Cho, B. R. (2010) · Chemistry - An Asian Journal · doi:10.1002/asia.201000542 · Cited by 131 · see citing works
Synthesis of Rhodamines from Fluoresceins Using Pd-Catalyzed C–N Cross-Coupling
Grimm, J. B., & Lavis, L. D. (2011) · Organic Letters · doi:10.1021/ol202618t · Cited by 128 · see citing works
Two-photon fluorescent probes for acidic vesicles in live cells and tissue.
Kim, H., An, M., Hong, J.-H., Jeong, B., Kwon, O., Hyon, J.-Y., Hong, S.-C., Lee, K. J., & Cho, B. (2008) · Angewandte Chemie · doi:10.1002/anie.200704586 · Cited by 120 · see citing works
Fluorescent Environment-Sensitive Dyes as Reporters of Biomolecular Interactions
Klymchenko, A. S., & Mély, Y. (2012) · Progress in molecular biology and translational science · doi:10.1016/b978-0-12-386932-6.00002-8 · Cited by 115 · see citing works
Jacobson, A. F., Petrič, A., Hogenkamp, D., et al. (1996) · Journal of the American Chemical Society · doi:10.1021/ja9543356 · Cited by 104 · see citing works
Kim, D., Sambasivan, S., Nam, H., Kim, K. H., Kim, J. Y., Joo, T., Lee, K., Kim, K., & Ahn, K. H. (2012) · Chemical Communications · doi:10.1039/c2cc32424e · Cited by 103 · see citing works
Self-citationReaction-Based Two-Photon Probes for Mercury Ions: Fluorescence Imaging with Dual Optical Windows
Rao, A. S., Kim, D., Wang, T., et al. (2012) · Organic Letters · doi:10.1021/ol3009057 · Cited by 103 · see citing works
Self-citationLi, L., Shen, X., Xu, Q., & Yao, S. Q. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201205940 · Cited by 96 · see citing works
Construction of a Library of Rhodol Fluorophores for Developing New Fluorescent Probes
Peng, T., & Yang, D. (2010) · Organic Letters · doi:10.1021/ol902706b · Cited by 95 · see citing works
Lu, Z., Lord, S. J., Wang, H., et al. (2006) · The Journal of Organic Chemistry · doi:10.1021/jo0616660 · Cited by 87 · see citing works
Parusel, A. B. J., Nowak, W., Grimme, S., et al. (1998) · The Journal of Physical Chemistry A · doi:10.1021/jp981540+ · Cited by 68 · see citing works
Singlet adiabatic states of solvated PRODAN: a semiempirical molecular orbital study
Ilich, P., & Prendergast, F. G. (1989) · The Journal of Physical Chemistry · doi:10.1021/j100348a014 · Cited by 68 · see citing works
Park, M., Kim, C. H., & Joo, T. (2012) · The Journal of Physical Chemistry A · doi:10.1021/jp310842z · Cited by 63 · see citing works
Self-citationLoving, G. S., & Imperiali, B. (2009) · Bioconjugate Chemistry · doi:10.1021/bc900319z · Cited by 55 · see citing works
A Small‐Molecule Two‐Photon Probe for Nitric Oxide in Living Tissues
Seo, E. W., Han, J. H., Heo, C. H., et al. (2012) · Chemistry - A European Journal · doi:10.1002/chem.201201197 · Cited by 53 · see citing works
Nowak, W., Adamczak, P., Balter, A., et al. (1986) · Journal of Molecular Structure THEOCHEM · doi:10.1016/0166-1280(86)80103-8 · Cited by 52 · see citing works
An ab initio study on excited and ground state properties of the organic fluorescence probe PRODAN
Parusel, A. B. J., Schneider, F. W., & Köhler, G. (1997) · Journal of Molecular Structure THEOCHEM · doi:10.1016/s0166-1280(96)05002-6 · Cited by 41 · see citing works
Petrič, A., Johnson, S. A., Pham, H. V., et al. (2012) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1214134109 · Cited by 39 · see citing works
Two-photon probes for biomedical applications
Lim, C. S., & Cho, B. R. (2013) · BMB Reports · doi:10.5483/bmbrep.2013.46.4.045 · Cited by 36 · see citing works
Protein structure: Polar pocket with nonpolar lining
Cowley, D. J. (1986) · Nature · doi:10.1038/319014a0 · Cited by 31 · see citing works
Rao, A. S., Singha, S., Choi, W., et al. (2012) · Organic & Biomolecular Chemistry · doi:10.1039/c2ob26000j · Cited by 30 · see citing works
Self-citationLocal Solvent Acidities in β-Cyclodextrin Complexes with PRODAN Derivatives
Naughton, H., & Abelt, C. J. (2013) · The Journal of Physical Chemistry B · doi:10.1021/jp400765x · Cited by 27 · see citing works
Carbonyl-Twisted 6-Acyl-2-dialkylaminonaphthalenes as Solvent Acidity Sensors
Green, A. M., Naughton, H., Nealy, Z. B., et al. (2012) · The Journal of Organic Chemistry · doi:10.1021/jo301263g · Cited by 19 · see citing works
Steffen Jockusch, B., Zheng, Q., He, G. S., Pudavar, H. E., Yee, D. J., Balšánek, V., Halim, M., Sameš, D., Prasad, P. N., & Turro, N. J. (2007) · The Journal of Physical Chemistry C · doi:10.1021/jp067430h · Cited by 18 · see citing works
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Research works printed but not linked: 2
- (a) Jockusch S. Zheng Q. He G. S. Pudavar H. E. Yee D. J. Balsanek V. Halim M. Sames D. Prasad P. N. Turro N. J. J. Phys. Chem. C 2007 111 8872 8877 (b) Kim H. M. Cho B. R. Chem. - Asian J. 2011 6 58 69 20963746 (c) Li L. Zhang C.-W. Chen G. Y. J. Zhu B. Chai C. Xu Q.-H. Tan E.-K. Zhu Q. Lim K.-L. Yao S. Q. Nat. Commun. 2014 5 3276 24522637 (d) Lee J. H. Lim C. S. Tian Y. S. Han J. H. Cho B. R. J. Am. Chem. Soc. 2010 132 1216 1217 20052975
- 1% DMSO was added to dissolve the compounds in water. No positive DLS data for nanoparticle formation in aqueous solution was observed under our experimental conditions, excluding the possibility of nanoparticle formation in aqueous media that was observed under special experimental conditions for acedan derivatives (see details in ESI): Yao Y. W. Yan Y. Xue L. Zhang C. Li G. Zheng Q. Zhao Y. S. Jiang H. Yao J., Angew. Chem., Int. Ed., 2013, 52, 8713 – 8717.
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- Authors
- Singha, S., Kim, D., Roy, B., Sambasivan, S., Moon, H., Rao, A. S., Kim, J. Y., Joo, T., Park, J. W., Rhee, Y. M., Wang, T., Kim, K. H., Shin, Y. H., Jung, J., & Ahn, K. H.
- Affiliations
- Pohang University of Science and Technology (KR)
- Kyung Hee University (KR)
- Corresponding author
- Joo, Taiha
- Rhee, Young Min
- Kim, Ki Hean
- Jung, Junyang
- Ahn, Kyo Han
- ORCID
- Venue
- Chemical Science
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2015
- Volume
- 6
- Issue
- 7
- Pages
- 4335-4342
- ISSN
- 2041-6520 (ISSN-L)
- 2041-6539
- PMC
- PMC5707477
- OpenAlex
- W2103100725
- Cited by
- 170
- References
- 50
- Citations by year
- 2026: 11 · 2025: 9 · 2024: 13 · 2023: 17 · 2022: 17 · 2021: 12 · 2020: 24 · 2019: 20 · 2018: 16 · 2017: 17 · 2016: 11 · 2015: 3
- FWCI
- 6.99
- Type
- journal article
- Language
- en
- Open access
- diamond
- doi.org
- Licence
- cc-by
- Locations
- Chemical Science (publishedVersion, cc-by)
- Europe PMC (PubMed Central) (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Open Access System for Information Sharing (Pohang University of Science and Technology) (submittedVersion)
- Funders
- Ministry of Health and Welfare (HI13C1378)
- National Research Foundation (2014K1A1A2064569)
- Ministry of Science, ICT and Future Planning
- National Research Foundation of Korea (2007-0056330, 2014-R1A2A1A12067510, 2012-0009380)
- Topics
- Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
- Keywords
- water solubility, structural modification, two-photon microscopy, fluorescent probes
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