Excited-state intramolecular proton transfer (ESIPT) and charge transfer (CT) fluorescence probe for model membranes

Dennison, S. Moses; Guharay, Jayanti; Sengupta, Pradeep K.

doi:10.1016/s1386-1425(99)00013-x

Cited by 79 publications

(41 citation statements)

References 25 publications

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“…The red-edge effects for ESPT in different 3-hydroxyflavone derivatives were studied in different heterogenic and motionally restricted environmentsmicelles and lipid bilayers (96)(97)(98)(99), protein molecules (25, 100), phospholipid bilayers (101) and cell membranes (102). In all cases, photoselection at the red-edge suppressed the PT reaction.…”

Section: Excited-state Proton Transfermentioning

confidence: 99%

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The red‐edge effects: 30 years of exploration

2002

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In 1970, three laboratories independently made a discovery that, for aromatic fluorophores embedded into different rigid and highly viscous media, the spectroscopic properties do not conform to classical rules. The fluorescence spectra can depend on excitation wavelength, and the excited-state energy transfer, if present, fails at the "red" excitation edge. These red-edge effects were related to the existence of excited-state distribution of fluorophores on their interaction energy with the environment and the slow rate of dielectric relaxation of this environment. In these conditions the site-selection can be provided by variation of the energy of illuminating light quanta, and the behaviour of selected species can be followed as a function of time and other variables. These observations found extensive application in different areas of research: colloid and polymer science, molecular biophysics, photochemistry and photobiology. In particular, they led to the development of very productive methods of studying the dynamics of dielectric relaxations in protein and membranes, using the tryptophan emission and the emission of a variety of probes. These studies were extended to the time domain with the observation of new site-selective effects in emission intensity and anisotropy decays. They stimulated the emergence and development of cryogenic energy-selective and single-molecular techniques that became valuable tools in their own right in chemistry and biophysics research. Site-selection effects were discovered for electron-transfer and proton-transfer reactions if they depended on the dynamics of the environment. This review is focused on the progress in the field of red-edge effects, their applications and prospects.

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Section: Excited-state Proton Transfermentioning

confidence: 99%

“…Phospholipid head groups modified by the 7-nitrobenz-2-oxa-1,3-diazole (NBD) fluorophore probably do not extend to the membrane surface, which follows from a detectable REE (132). Strong static REE was recorded recently for a 3-hydroxyflavone derivative (99).…”

Section: Phospholipid Vesiclesmentioning

confidence: 99%

The red‐edge effects: 30 years of exploration

2002

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“…2 Measurements of the intensity ratio of the N* and T* bands, I N* /I T* , are very attractive possibilities to perform ratiometric detection, independent of dye concentration and instrumental settings. 3,4 Due to these unique features, numerous 3HC dyes have been synthesized and studied, resulting in the development of new fluorescent probes for solvent polarity, 2,5,6 ion binding 7 and electric fields 8,9 with applications in the fields of polymers, 10 reverse micelles, 11,12 host-guest complexes 13 , lipid vesicles, 9,14-17 cellular membranes 18 and proteins. [19][20][21][22][23] Reactive derivatives of 3HCs have been also proposed for fluorescence labelling of biomolecules in order to study their conformations and intermolecular interactions.…”

Section: Introductionmentioning

confidence: 99%

Effects of polar protic solvents on dual emissions of 3-hydroxychromones

et al. 2007

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3-Hydroxychromones (3HC), exhibit dual emissions highly sensitive to solvent properties due to excited state intramolecular proton transfer (ESIPT). Therefore, 3HCs find wide applications as fluorescence probes in biological systems. Here, it is particularly important to understand the fluorescence behaviour of 3HCs in polar environments. Herein, we studied 3-hydroxyflavone, 2-(2-furyl)-3-hydroxychromone and 2-(2-benzofuryl)-3-hydroxychromone in high polarity solvents characterized by different H-bond donor abilities, donor concentrations and acceptor abilities. Our results show that the dual emissions of the dyes are insensitive to solvent basicity but strongly depend on the two other parameters. Moreover, furyl-and benzofuryl-substituted dyes were significantly more sensitive than the 3-hydroxyflavone to H-bond donor ability, while all three dyes showed roughly equivalent high sensitivity to H-bond donor concentration. These results can be explained by different mechanisms. Thus, the sensitivity of all three dyes to increasing concentrations of H-bond donors probably results from increase in the population of solvated dye with disrupted intramolecular H-bonds. Meantime, the sensitivity to Hbond donor ability of the solvent, observed mainly with furyl and benzofuryl dyes, is probably related to the strength of the H-bonds between the solvent and the 4-carbonyl group of the dye with intact intramolecular H-bonds. The present results provide new insights for further applications of 3HC derivatives as environment-sensitive probes and labels of biological molecules.

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“…32 A solution of silica nanobubbles prepared using the same method without aniline did not show any peak when analysed by fluorescence spectroscopy. To make sure that aniline molecule is indeed inside the shell, we measured the emission spectrum of the supernatant solution obtained after centrifuging the aniline@SiO 2 solution for around six hours at 2000 rpm.…”

Section: Wavelength Nmmentioning

confidence: 96%

Aniline incorporated silica nanobubbles

et al. 2006

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Abstract.We report the synthesis of stearate functionalized nanobubbles of SiO 2 with a few aniline molecules inside, represented as C 6 H 5 NH 2 @SiO 2 @stearate, exhibiting fluorescence with red-shifted emission. Stearic acid functionalization allows the materials to be handled just as free molecules, for dissolution, precipitation, storage etc. The methodology adopted involves adsorption of aniline on the surface of gold nanoparticles with subsequent growth of a silica shell through monolayers, followed by the selective removal of the metal core either using sodium cyanide or by a new reaction involving halocarbons. The material is stable and can be stored for extended periods without loss of fluorescence. Spectroscopic and voltammetric properties of the system were studied in order to understand the interaction of aniline with the shell as well as the monolayer, whilst transmission electron microscopy has been used to study the silica shell.

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Excited-state intramolecular proton transfer (ESIPT) and charge transfer (CT) fluorescence probe for model membranes

Cited by 79 publications

References 25 publications

The red‐edge effects: 30 years of exploration

The red‐edge effects: 30 years of exploration

Effects of polar protic solvents on dual emissions of 3-hydroxychromones

Aniline incorporated silica nanobubbles

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