Sibling rivalry: intrinsic luminescence from two xanthene dye monoanions, resorufin and fluorescein, provides evidence for excited-state proton transfer in the latter

Excited-state proton transfer in gas-phase fluorescein monoanions results in a broad, featureless emission band and a large Stokes shift compared to resorufin, which shares the same xanthene core structure.

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Design of Large Stokes Shift Fluorescent Proteins Based on Excited State Proton Transfer of an Engineered Photobase

Journal of the American Chemical Society ◽

10.1021/jacs.1c05039 ◽

2021 ◽

Vol 143 (37) ◽

pp. 15091-15102

Author(s):

Elizabeth M. Santos ◽

Wei Sheng ◽

Rahele Esmatpour Salmani ◽

Setare Tahmasebi Nick ◽

Alireza Ghanbarpour ◽

...

Keyword(s):

Excited State ◽

Proton Transfer ◽

Fluorescent Proteins ◽

Stokes Shift ◽

Large Stokes Shift ◽

Excited State Proton Transfer

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Excited‐state proton transfer in gas‐phase clusters: 2‐Naphthol⋅(NH3)n

The Journal of Chemical Physics ◽

10.1063/1.458693 ◽

1990 ◽

Vol 93 (7) ◽

pp. 4520-4532 ◽

Cited By ~ 59

Author(s):

Thierry Droz ◽

Richard Knochenmuss ◽

Samuel Leutwyler

Keyword(s):

Excited State ◽

Proton Transfer ◽

Gas Phase ◽

Gas Phase Clusters ◽

Excited State Proton Transfer

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An NIR-emitting lysosome-targeting probe with large Stokes shift via coupling cyanine and excited-state intramolecular proton transfer

Chemical Communications ◽

10.1039/c7cc00700k ◽

2017 ◽

Vol 53 (26) ◽

pp. 3697-3700 ◽

Cited By ~ 73

Author(s):

Dipendra Dahal ◽

Lucas McDonald ◽

Xiaoman Bi ◽

Chathura Abeywickrama ◽

Farai Gombedza ◽

...

Keyword(s):

Excited State ◽

Proton Transfer ◽

Stokes Shift ◽

Intramolecular Proton Transfer ◽

Large Stokes Shift

A NIR-emitting probe with a large Stokes shift (Δλ ≈ 234 nm) can selectively show lysosome organelles without exhibiting “an alkalinizing effect”.

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Excited-State Proton Transfer in Fluorescent Photoactive Yellow Protein Containing 7-Hydroxycoumarin

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.896.85 ◽

2014 ◽

Vol 896 ◽

pp. 85-88

Author(s):

Dian Novitasari ◽

Hironari Kamikubo ◽

Yoichi Yamazaki ◽

Mariko Yamaguchi ◽

Mikio Kataoka

Keyword(s):

Hydrogen Bonding ◽

Excited State ◽

Proton Transfer ◽

Fluorescent Protein ◽

Stokes Shift ◽

Spectroscopic Studies ◽

Photoactive Yellow Protein ◽

Excited State Proton Transfer ◽

Hydrogen Bonding Network ◽

Green Fluorescent

Green fluorescent protein (GFP) has been used as an effective tool in various biological fields. The large Stokes shift resulting from an excited-state proton transfer (ESPT) is the basis for the application of GFP in such techniques as ratiometric GFP biosensors. The chromophore of GFP is known to be involved in a hydrogen-bonding network. Previous X-ray crystallographic and FTIR studies suggest that a proton wire along the hydrogen-bonding network plays a role in the ESPT. In order to examine the relationship between the ESPT and hydrogen-bonding network within proteins, we prepared an artificial fluorescent protein using a light-sensor protein, photoactive yellow protein (PYP). The native chromophore of p-coumaric acid (pCA) of PYP undergoes trans-cis isomerization after absorbing a photon, which triggers proton transfers within the hydrogen-bonding network comprised of pCA and proximal amino acid residues. Although PYP emits little fluorescence, we succeeded to reconstitute an artificial fluorescent PYP (PYP-coumarin) by substituting the pCA with its trans-lock analog 7-hydroxycoumarin. Spectroscopic studies with PYP-coumarin revealed that the chromophore takes an anionic form at neutral pH, but is protonated by lowering pH. Both the protonated and deprotonated forms of PYP-coumarin emit intense fluorescence, as compared with the native PYP. In addition, both the deprotonated and protonated forms show identical λmax values in their fluorescence spectra, indicating that ESPT occurs in the artificial fluorescent protein.

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Excited state proton transfer in 2′-hydroxychalcone derivatives

Physical Chemistry Chemical Physics ◽

10.1039/c6cp07541j ◽

2017 ◽

Vol 19 (3) ◽

pp. 2409-2416 ◽

Cited By ~ 24

Author(s):

Michael Dommett ◽

Rachel Crespo-Otero

Keyword(s):

Excited State ◽

Solid State ◽

Proton Transfer ◽

Gas Phase ◽

Theoretical Investigation ◽

Excited State Proton Transfer

ESIPT-active solid-state emitters based on 2-hydroxychalcone are almost non-emissive in solution but emit in the deep red/NIR region when crystalline. A comprehensive theoretical investigation of the gas-phase excited state relaxation pathways in five 2-hydroxychalcone systems is presented, using a combination of static and non-adiabatic simulations.

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A novel 2-(2′-aminophenyl)benzothiazole derivative displays ESIPT and permits selective detection of Zn2+ ions: experimental and theoretical studies

RSC Advances ◽

10.1039/c6ra09713h ◽

2016 ◽

Vol 6 (75) ◽

pp. 71496-71500 ◽

Cited By ~ 5

Author(s):

Subramaniyan Janakipriya ◽

Selvaraj Tamilmani ◽

Sathiah Thennarasu

Keyword(s):

Excited State ◽

Proton Transfer ◽

Stokes Shift ◽

Intramolecular Proton Transfer ◽

Theoretical Studies ◽

Selective Detection ◽

Large Stokes Shift ◽

Benzothiazole Derivative ◽

Experimental And Theoretical Studies

Synthesis of a novel 2-(2′-aminophenyl)benzothiazole based probe (1) and demonstration of excited state intramolecular proton transfer (ESIPT) with a large Stokes shift (∼246 nm) are presented.

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