2022
DOI: 10.1021/acs.jpclett.2c02287
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Improving the Brightness of Pyronin Fluorophore Systems through Quantum-Mechanical Predictions

Abstract: The pyronin class of fluorophores serves a critical role in numerous imaging applications, particularly involving preferential staining of RNA through base pair intercalation. Despite this important role in molecular staining applications, the same set of century-old pyronins (i.e., pyronin Y (PY) and pyronin B (PB)), which possess relatively low fluorophore brightness, are still predominantly being used due to the lack of methodology for generating enhanced variants. Here, we use TD-DFT calculations of interc… Show more

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Cited by 2 publications
(3 citation statements)
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“…This can occur when alkyl-substituted aryl-amino groups (e.g., the dimethyl amine group in [PY] + ) rotate out of conjugation with the π-system. 18,40 [PY] • appears to undergo an analogous twisting deformation upon photoexcitation. The phenomenon of a dark or weakly emitting neutral and strongly fluorescent cation is surprisingly rare among molecular chromophores.…”
Section: Next We Discuss the Possible Contributions Of The Neutral [Py]mentioning
confidence: 99%
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“…This can occur when alkyl-substituted aryl-amino groups (e.g., the dimethyl amine group in [PY] + ) rotate out of conjugation with the π-system. 18,40 [PY] • appears to undergo an analogous twisting deformation upon photoexcitation. The phenomenon of a dark or weakly emitting neutral and strongly fluorescent cation is surprisingly rare among molecular chromophores.…”
Section: Next We Discuss the Possible Contributions Of The Neutral [Py]mentioning
confidence: 99%
“…It is a well-known, bright green-yellow fluorophore and the most commonly utilized fluorescent probe among the pyronin family ([PY] + , pyronin B, and acridine red) . Since its first synthesis in 1894, , the fluorescent and selective RNA staining properties of pyronin Y and its synthetically tailored derivatives have been exploited in many applications, e.g., in histochemistry, , optoelectronics, , and microscopy. , As a result, pyronin Y has also been the subject of many experimental and theoretical studies to better understand its spectral properties, e.g., toward improving fluorescence quantum yields (Φ f ) and enhancing molar absorptivity by appropriate functionalization. Despite this intense activity, a molecular-level description of the vibronic properties of this model fluorophore with high spectroscopic accuracy is still missing. This reflects the inherent difficulty of selectively preparing well-defined samples of charged chromophores for spectroscopy.…”
mentioning
confidence: 99%
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