A comparative study of the photophysics of phenyl, thienyl, and chalcogen substituted rhodamine dyes

Sabatini, Randy P.; Mark, Manfred J.; Mark, Daniel J.; Kryman, Mark W.; Hill, Joseph C.; Brennessel, William W.; Detty, Michael R.; Eisenberg, Richard; McCamant, David W.

doi:10.1039/c6pp00233a

Cited by 21 publications

(48 citation statements)

References 51 publications

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“…has also been reported in the Rhodamine literature for a range of ultrafast optical experiments from transient gratings to transient absorptions [19,41,43]. A slightly shorter timescale of 1.4 ps was observed in the transient absorption spectra of RhB in MeCN and extracted through a global analysis and assigned to a narrow spectral feature [19]. The longer timescale observed here may be related to the higher polarity of the solvent.…”

Section: Zwitterionsupporting

confidence: 81%

“…In previous works on Rh6G this short timescale has been observed but was assigned exclusively to ultrafast photoinduced electron transfer [42]. has also been reported in the Rhodamine literature for a range of ultrafast optical experiments from transient gratings to transient absorptions [19,41,43]. A slightly shorter timescale of 1.4 ps was observed in the transient absorption spectra of RhB in MeCN and extracted through a global analysis and assigned to a narrow spectral feature [19].…”

Section: Zwitterionsupporting

confidence: 55%

“…The main point being that if the rotation about the amino C-N bond cannot take place the twisted state cannot be formed and thus no quenching occurs. This model continues to expound support with a very recent comprehensive study which examined the photophysics of phenyl, thienyl and chalcogen substituted Rhodamine dyes also siding with this analysis of the photophysics [19]. Another theory involves the amino groups and their umbrella-like motion.…”

Section: Introductionmentioning

confidence: 64%

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A combined theoretical and experimental study of the ultrafast photophysics of Rhodamine B

et al. 2018

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The ultrafast dynamics of zwitterionic and cationic Rhodamine B in ethanol have been investigated using TDDFT calculations and ultrafast transient absorption spectroscopy. The calculations show that the zwitterionic form exhibits an electronically excited dark state which could potentially quench the initially photoexcited state, while in the case of cationic form the lowest excited lying dark state is outside the energy region of interest and cannot explain its quenching. Due to similarities in the relaxation dynamics of the two molecules, it is suggested that the electronically excited dark state may not play such an important role in the quenching process of this dye as previously proposed. Experimental evidence presented suggests that a quenching mechanism is active on the picosecond timescale for both forms of Rhodamine B.

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Section: Zwitterionsupporting

confidence: 81%

Section: Zwitterionsupporting

confidence: 55%

Section: Introductionmentioning

confidence: 64%

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A combined theoretical and experimental study of the ultrafast photophysics of Rhodamine B

et al. 2018

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“…The fluorescence of rhodamine dyes (Figure I) has several desirable photophysical properties [66][67][68][69]. One of these is the pH insensitivity of the fluorescence intensity of this family of dyes [70].…”

Section: Box 2 Mitochondrial Molecular Thermometry Using Fluorescent Dyesmentioning

confidence: 99%

The hot mitochondrion paradox: reconciling theory and experiment

Fahimi

Matta

2022

Trends in Chemistry

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Experiments by Chrétien and coworkers suggest that mitochondria are 10°C hotter than their surroundings. Steady-state theoretical estimates place this difference at a maximum of 10 −5 °C. This millionfold disagreement may be called the 'hot mitochondrion paradox'. It is suggested that every proton translocated via ATP synthase sparks a picosecond temperature-difference spike of the order of magnitude measured by Chrétien et al. Time averaging of these spikes recovers the theoretical value. Further, a temporal and spatial superposition of the fluorescence intensity of a very large number of molecular thermometer molecules in the sample can give the appearance of a steady signal. The inner mitochondrial membrane appears to be flanked by temperature differences fluctuating in time and along the membrane's surface, with 'hot' and 'cold' spots as ultrashort temperature spikes. An apparent millionfold disagreement of theory and experiment HighlightsExperiments suggest a 10°C temperature difference between the mitochondrion and its surroundings in a millionfold disagreement with steadystate theoretical estimates.Both experiment and theory appear to be solidly founded, so we have a paradox.ATP synthase is modelled as a modified Feynman ratchet engine coupling two separate heat baths.The paradox is resolved by understanding that the appearance of the steady measurement of a temperature difference is the result of continually recording sharp, picosecond spikes of temperature difference the time averaging of which leads to the theoretical value.

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“…The transient spectra of 1 in methanol ( c =5×10 −4 mol dm −3 ) were recorded using 100‐fs steps up to a 10 ps delay after the pump pulse ( λ exc =280 nm). Fitting with a single exponential decay resulted in the spectra of two species with λ max =465 nm (lifetime τ =(1.1±0.1) ns) and λ max =425 nm ( τ ∼3 ns; Figure ), which were assigned to the singlet ( 1 1 *) and triplet ( 3 1 *) excited states, respectively, because their spectral features were similar to those of analogous singlet‐ and triplet‐excited Si‐rhodamines or phenyl and thienyl rhodamines …”

Section: Resultsmentioning

confidence: 99%

Photochemistry of a 9‐Dithianyl‐Pyronin Derivative: A Cornucopia of Reaction Intermediates Lead to Common Photoproducts

et al. 2020

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Leaving groups attached to the meso‐methyl position of many common dyes, such as xanthene, BODIPY, or pyronin derivatives, can be liberated upon irradiation with visible light. However, the course of phototransformations of such photoactivatable systems can be quite complex and the identification of reaction intermediates or even products is often neglected. This paper exemplifies the photochemistry of a 9‐dithianyl‐pyronin derivative, which undergoes an oxidative transformation at the meso‐position to give a 3,6‐diamino‐9H‐xanthen‐9‐one derivative, formic acid, and carbon monoxide as the main photoproducts. The course of this multi‐photon multi‐step reaction was studied under various conditions by steady‐state and time‐resolved optical spectroscopy, mass spectrometry and NMR spectroscopy to understand the effects of solvents and molecular oxygen on individual steps. Our analyses have revealed the existence of many intermediates and their interrelationships to provide a complete picture of the transformation, which can bring new inputs to a rational design of new photoactivatable pyronin or xanthene derivatives.

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A comparative study of the photophysics of phenyl, thienyl, and chalcogen substituted rhodamine dyes

Abstract: We characterize the ultrafast photophysics and electrochemistry of a collection of rhodamine-style dyes and show that different dyes exhibit various directions of charge-transfer in the excited state.

Cited by 21 publications

References 51 publications

A combined theoretical and experimental study of the ultrafast photophysics of Rhodamine B

A combined theoretical and experimental study of the ultrafast photophysics of Rhodamine B

The hot mitochondrion paradox: reconciling theory and experiment

Photochemistry of a 9‐Dithianyl‐Pyronin Derivative: A Cornucopia of Reaction Intermediates Lead to Common Photoproducts

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