Fluorescence and photoinduced proton transfer in the protolytic forms of fluorescein: Experimental and computational study

Gerasimova, M. A.; Tomilin, Felix N.; Malyar, Elena Yu.; Varganov, Sergey A.; Fedorov, Dmitri G.; Овчинников, С. Г.; Slyusareva, E. A.

doi:10.1016/j.dyepig.2019.107851

Cited by 33 publications

(32 citation statements)

References 55 publications

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“…For open form B , absorption spectra consist of two maxima of appropriately equal intensity at 455 nm and 475 nm. Moreover, the shoulder at around 420 nm is visibly associated with the xanthene ring [ 55 , 56 ]. For closed forms A , wide bands with one maximum can be observed.…”

Section: Resultsmentioning

confidence: 99%

Controlled Synthesis of Luminescent Xanthene Dyes and Use of Ionic Liquid in Thermochromic Reaction

2022

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In this study, we demonstrate six novel xanthene derivatives and their spectroscopic and chemical properties. The presented synthesis examination allowed us to obtain two different compounds during one step, with open and closed lactone rings substituted with different length alkyl chains. Increasing the reaction efficiency to 77% was obtained using the microwave-assisted method. Moreover, the modification of O-alkylation synthesis in an ecofriendly way using a ball mill led to achieving exclusively one opened ring product. All of the synthesized compounds showed different spectroscopic behaviors in comparison with the different organic dyes; the typical concentration quenching of luminescence was not observed. The relationship between the length of the alkyl chain and the time of luminescence decay is presented. Synthetized closed forms of dyes turned out to be promising leuco dyes. For the first time, an ionic liquid was used as a developer of synthesized xanthene derivatives (as leuco dyes), which led to obtaining an irreversible thermochromic marker.

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Section: Resultsmentioning

confidence: 99%

Controlled Synthesis of Luminescent Xanthene Dyes and Use of Ionic Liquid in Thermochromic Reaction

2022

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“…Fluorescein luminescence is strongly dependent on solvent pH, and changes in pH are visible in the shape of emission spectra, quantum yield values, and decay times [ 4 , 5 , 7 , 42 ]. Fluorescein occurs in several prototropic forms—cationic, neutral, and anionic (including monoanion and dianion), but because of its superior quantum efficiency, is mostly used in dianionic form [ 43 , 44 ].…”

Section: Resultsmentioning

confidence: 99%

“…The structure of product B, on the other hand, did not allow for the formation of a monoanion or dianion form. This was crucial, since the UV–Vis absorption and emission spectra of the neutral form were similar to the monoanion one (owing to little participation of the carboxyl group in ionization [ 7 ]).…”

Section: Resultsmentioning

confidence: 99%

“…The various forms reported in the literature are cationic, neutral form with three structures (quinoid, lactone, and zwitterionic), monoanionic, and dianionic [ 5 , 6 ]. Calculations for the determination of their electronic structure were carried out using computational methods [ 7 ]. It has also been reported that colorless forms of lactone and colored quinoid occur in equilibrium in aqueous solutions [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

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Development of Efficient One-Pot Methods for the Synthesis of Luminescent Dyes and Sol–Gel Hybrid Materials

et al. 2021

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This paper presents a comparison of the simultaneous preparation of di-O-alkylated and ether–ester derivatives of fluorescein using different methods (conventional or microwave heating). Shortening of the reaction time and increased efficiency were observed when using a microwave reactor. Moreover, described here for the first time is the application of a fast, simple, and eco-friendly ball-assisted method to exclusively obtain ether–ester derivatives. We also demonstrate that fluorescein can be effectively functionalized by O-alkylation carried out under microwave or ball-milling conditions, saving time and energy and affording the desired products with good yields and minimal byproduct formation. All the synthesized products as well as pH-dependent (prototropic) forms trapped in the SiO2 matrix were examined using UV–Vis and fluorescence spectroscopy.

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“…According to previous work, only monoanion and dianion forms emit (structures shown in Figure 2). [ 23 ] The absorption and emission spectra in neutral pH 7.3 and basic pH 9.5 solutions are displayed in Figure 3. Ethanol was selected in the MEF experiments as the solvent because of less toxicity and better solubility.…”

Section: Resultsmentioning

confidence: 99%

Investigating metal‐enhanced fluorescence effect on fluorescein by gold nanotriangles and nanocubes using time‐resolved fluorescence spectroscopy

Luo

Lai

Lee

et al. 2021

J Chinese Chemical Soc

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Gold nanotriangles (AuNTs) and nanocubes (NCs) coated with silica shell and fluorescein were synthesized to study the effects of metal‐enhanced fluorescence. The interaction between gold nanoparticles (GNPs) and fluorescein with silica shells of different thicknesses as spacers was investigated by using time‐resolved fluorescence spectroscopy. From the biexponential decay of fluorescence of fluorophore and the kinetic mechanism for the interaction, we obtained the rate constants of energy transfer processes. Both energy transfer rates from fluorophore to the bright and dark modes of gold nanoparticles decreased with distance d (= silica thickness) with a dependence ∝ d−n and n ≈ 2. The rate constant of nanosurface energy transfer kNEST, considering dipolar interaction between fluorophore and metal surface, has an estimated value 1.7 times slower at d = 9 nm and about four times slower at 25 nm than the obtained rate constant for energy transfer from fluorophore to GNP dipolar mode in the AuNT system. For the AuNC system, the rate constants are greater than the AuNT system because of better spectral overlap between emission of fluorescein and surface plasmon resonance.

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Fluorescence and photoinduced proton transfer in the protolytic forms of fluorescein: Experimental and computational study

Cited by 33 publications

References 55 publications

Controlled Synthesis of Luminescent Xanthene Dyes and Use of Ionic Liquid in Thermochromic Reaction

Controlled Synthesis of Luminescent Xanthene Dyes and Use of Ionic Liquid in Thermochromic Reaction

Development of Efficient One-Pot Methods for the Synthesis of Luminescent Dyes and Sol–Gel Hybrid Materials

Investigating metal‐enhanced fluorescence effect on fluorescein by gold nanotriangles and nanocubes using time‐resolved fluorescence spectroscopy

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