Photobasicity-Triggered Twisted Intramolecular Charge Transfer of Push–Pull Chromophores

Fluorogenic probes that undergo excited-state proton transfer (ESPT) and twisted intramolecular charge transfer (TICT) offer tunable fluorescence properties for bioimaging and sensing applications. However, the relationship between ESPT and TICT remains poorly understood in push–pull chromophores. D...

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Published inThe journal of physical chemistry. B Vol. 129; no. 33; pp. 8485 - 8493
Main Authors Pounder, Austin, Pavlovic, Matteo, Chow, Darren, Regan, Keenan T., Chen, Aicheng, Wetmore, Stacey D., Manderville, Richard A.
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 21.08.2025
Subjects
B: Liquids; Chemical and Dynamical Processes in Solution
Online AccessGet full text
ISSN1520-6106
1520-5207
1520-5207
DOI10.1021/acs.jpcb.5c03367

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Abstract Fluorogenic probes that undergo excited-state proton transfer (ESPT) and twisted intramolecular charge transfer (TICT) offer tunable fluorescence properties for bioimaging and sensing applications. However, the relationship between ESPT and TICT remains poorly understood in push–pull chromophores. Despite extensive research on photoacids, photobases remain underutilized as fluorescence modulators, and the roles of solvent polarity, acidity, and donor–acceptor strength in governing photobasicity and TICT activation are not well established. We conducted photophysical experiments and (TD)-DFT calculations to explore how protonation and solvent interactions influence fluorescence behavior. Our findings reveal that while protonation consistently induces red-shifted absorption and emission, ESPT efficiency and TICT formation vary widely depending on molecular structure and solvent environment. This work provides new insights into photobasicity-driven fluorescence modulation, offering a foundation for designing next-generation probes with enhanced sensitivity to local acidity, viscosity, and microenvironmental factors.
AbstractList Fluorogenic probes that undergo excited-state proton transfer (ESPT) and twisted intramolecular charge transfer (TICT) offer tunable fluorescence properties for bioimaging and sensing applications. However, the relationship between ESPT and TICT remains poorly understood in push-pull chromophores. Despite extensive research on photoacids, photobases remain underutilized as fluorescence modulators, and the roles of solvent polarity, acidity, and donor-acceptor strength in governing photobasicity and TICT activation are not well established. We conducted photophysical experiments and (TD)-DFT calculations to explore how protonation and solvent interactions influence fluorescence behavior. Our findings reveal that while protonation consistently induces red-shifted absorption and emission, ESPT efficiency and TICT formation vary widely depending on molecular structure and solvent environment. This work provides new insights into photobasicity-driven fluorescence modulation, offering a foundation for designing next-generation probes with enhanced sensitivity to local acidity, viscosity, and microenvironmental factors.
Fluorogenic probes that undergo excited-state proton transfer (ESPT) and twisted intramolecular charge transfer (TICT) offer tunable fluorescence properties for bioimaging and sensing applications. However, the relationship between ESPT and TICT remains poorly understood in push-pull chromophores. Despite extensive research on photoacids, photobases remain underutilized as fluorescence modulators, and the roles of solvent polarity, acidity, and donor-acceptor strength in governing photobasicity and TICT activation are not well established. We conducted photophysical experiments and (TD)-DFT calculations to explore how protonation and solvent interactions influence fluorescence behavior. Our findings reveal that while protonation consistently induces red-shifted absorption and emission, ESPT efficiency and TICT formation vary widely depending on molecular structure and solvent environment. This work provides new insights into photobasicity-driven fluorescence modulation, offering a foundation for designing next-generation probes with enhanced sensitivity to local acidity, viscosity, and microenvironmental factors.Fluorogenic probes that undergo excited-state proton transfer (ESPT) and twisted intramolecular charge transfer (TICT) offer tunable fluorescence properties for bioimaging and sensing applications. However, the relationship between ESPT and TICT remains poorly understood in push-pull chromophores. Despite extensive research on photoacids, photobases remain underutilized as fluorescence modulators, and the roles of solvent polarity, acidity, and donor-acceptor strength in governing photobasicity and TICT activation are not well established. We conducted photophysical experiments and (TD)-DFT calculations to explore how protonation and solvent interactions influence fluorescence behavior. Our findings reveal that while protonation consistently induces red-shifted absorption and emission, ESPT efficiency and TICT formation vary widely depending on molecular structure and solvent environment. This work provides new insights into photobasicity-driven fluorescence modulation, offering a foundation for designing next-generation probes with enhanced sensitivity to local acidity, viscosity, and microenvironmental factors.
Author Regan, Keenan T.
Chen, Aicheng
Pavlovic, Matteo
Chow, Darren
Wetmore, Stacey D.
Manderville, Richard A.
Pounder, Austin
AuthorAffiliation Department of Chemistry & Biochemistry
University of Guelph
Department of Chemistry, Electrochemical Technology Center
Department of Chemistry & Toxicology
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Snippet Fluorogenic probes that undergo excited-state proton transfer (ESPT) and twisted intramolecular charge transfer (TICT) offer tunable fluorescence properties...
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SubjectTerms B: Liquids; Chemical and Dynamical Processes in Solution
Title Photobasicity-Triggered Twisted Intramolecular Charge Transfer of Push–Pull Chromophores
URI http://dx.doi.org/10.1021/acs.jpcb.5c03367
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