Excited State Intramolecular Proton Transfer and Metal Ion Complexation of 2-(2‘-Hydroxyphenyl)benzazoles in Aqueous Solution

2002 ◽  
Vol 106 (21) ◽  
pp. 5210-5220 ◽  
Author(s):  
Maged M. Henary ◽  
Christoph J. Fahrni
Keyword(s):  
Aqueous Solution ◽  
Excited State ◽  
Proton Transfer ◽  
Metal Ion ◽  
Intramolecular Proton Transfer ◽  
Metal Ion Complexation ◽  
Ion Complexation

A water soluble ESIPT-based fluorescent chemodosimeter for the ratiometric detection of palladium ions in aqueous solution and its application in live-cell imaging

2018 ◽  
Vol 42 (19) ◽  
pp. 15587-15592 ◽  
Author(s):  
Jing Huang ◽  
Yu Ding ◽  
Hongyu Fu ◽  
Bo Chen ◽  
Yifeng Han
Keyword(s):  
Aqueous Solution ◽  
Excited State ◽  
Proton Transfer ◽  
Live Cell Imaging ◽  
Cell Imaging ◽  
Intramolecular Proton Transfer ◽  
Live Cell ◽  
Water Soluble ◽  
Ratiometric Detection ◽  
Fluorescent Chemodosimeter

A new Excited State Intramolecular Proton Transfer (ESIPT) based water-soluble fluorescent chemodosimeter for the ratiometric detection of palladium ions has been rationally designed and developed.

Single excited state intramolecular proton transfer (ESIPT) chemodosimeter based on rhodol for both Hg2+ and OCl−: ratiometric detection with live-cell imaging

RSC Advances ◽  
2016 ◽  
Vol 6 (62) ◽  
pp. 57417-57423 ◽  
Author(s):  
Abhishek Manna ◽  
Debasish Sarkar ◽  
Shyamaprosad Goswami ◽  
Ching Kheng Quah ◽  
Hoong-Kun Fun
Keyword(s):  
Aqueous Solution ◽  
Excited State ◽  
Proton Transfer ◽  
Live Cell Imaging ◽  
Cell Imaging ◽  
Intramolecular Proton Transfer ◽  
Live Cell ◽  
Ratiometric Fluorescence ◽  
Ratiometric Detection

We have synthesised a ratiometric fluorescence chemodosimeter, STBR, for the detection of Hg2+ and OCl− in one platform over other cations, anions and oxidants in aqueous solution.

Photogeneration of 1,5-naphthoquinone methides via excited-state (formal) intramolecular proton transfer (ESIPT) and photodehydration of 1-naphthol derivatives in aqueous solution

2004 ◽  
Vol 82 (2) ◽  
pp. 240-253 ◽  
Author(s):  
Matthew Lukeman ◽  
Duane Veale ◽  
Peter Wan ◽  
V Ranjit N. Munasinghe ◽  
John ET Corrie
Keyword(s):  
Aqueous Solution ◽  
Excited State ◽  
Proton Transfer ◽  
Flash Photolysis ◽  
Laser Flash Photolysis ◽  
Intramolecular Proton Transfer ◽  
Photochemical Reactions ◽  
Quinone Methide ◽  
Phenol Derivatives ◽  
Naphthol Derivatives

The photochemistry of naphthols 1, 2, 4, 5 and 9, and phenol 10 has been studied in aqueous solution with the primary aim of exploring the viability of such compounds for naphthoquinone and quinone methide photogeneration, along the lines already demonstrated by our group for phenol derivatives. 1-Naphthol (1) is known to be substantially more acidic than 2-naphthol (2) in the singlet excited state (pKa* = 0.4 and 2.8, respectively) and it was expected that this difference in excited-state acidity might be manifested in higher reactivity of 1-naphthol derivatives for photochemical reactions requiring excited-state naphtholate ions, such as quinone methide formation. Our results show that three types of naphthoquinone methides (26a, 26b, and 27) are readily photogenerated in aqueous solution by irradiation of 1-naphthols. Photolysis of the parent 1-naphthol (1) in neutral aqueous solution gave 1,5-naphthoquinone methide 26a as well as the non-Kekulé 1,8-naphthoquinone methide 26b, both via the process of excited-state (formal) intramolecular proton transfer (ESIPT), based on the observation of deuterium exchange at the 5- and 8-positions, respectively, on photolysis in D2O–CH3CN. A transient assignable to the 1,5-naphthoquinone methide 26a was observed in laser flash photolysis experiments. The isomeric 2-naphthol (2) was unreactive under similar conditions. The more conjugated 1,5-naphthoquinone methide 27 was formed efficiently via photodehydroxylation of 4; isomeric 5 was unreactive. The efficient photosolvolytic reaction observed for 4 opens the way to design related naphthol systems for application as photoreleasable protecting groups by virtue of the long-wavelength absorption of the naphthalene chromophore.Key words: photosolvolysis, excited-state intramolecular proton transfer, quinone methide, photorelease, photoprotonation.

Protonation and metal-ion complexation in aqueous solution by pyridine-containing hexaaza macrocycles

1996 ◽  
pp. 1753 ◽  
Author(s):  
Karin I. Dhont ◽  
Gerrit G. Herman ◽  
Antonio C. Fabretti ◽  
Werner Lippens ◽  
Andr� M. Goeminne
Keyword(s):  
Aqueous Solution ◽  
Metal Ion ◽  
Metal Ion Complexation ◽  
Ion Complexation

Synthesis and metal ion complexation behavior of polycarboxylate 18-crown-6 ethers derived from tartaric acid

1988 ◽  
Vol 66 (5) ◽  
pp. 1097-1108 ◽  
Author(s):  
Philip J. Dutton ◽  
Thomas M. Fyles ◽  
Susan J. McDermid
Keyword(s):  
Aqueous Solution ◽  
Crown Ether ◽  
Tartaric Acid ◽  
Metal Ion ◽  
Electrostatic Interactions ◽  
Complexing Agents ◽  
Acidity Constants ◽  
Metal Ion Complexation ◽  
Ion Complexation ◽  
Anionic Charge

The metal ion complexation behavior of four 18-crown-6 ethers derived from (+)- and meso-tartaric acid is examined. Preparations of a meso-crown ether diacid and of a crown ether hexacid from three units of (+)-tartaric acid are described. Acidity constants and stability constants for complexation of metal cations in aqueous solution were determined by potentiometric titration. The complexes are substantially stabilized by favourable electrostatic interactions and are of similar stability to complexes of cryptands and EDTA. The complexation behavior of the series can be rationalized in terms of electrostatic interactions, direct coordination of the cations by at least one carboxylate from the crown ether periphery, and rigidification of the ligands as the anionic charge increases. Distributions of charge influence the relative stability of isomeric complexes. Highly charged polycarboxylate crown ethers are effective, but relatively unselective, cation complexing agents for a range of cations. The complexes are stable to pH 3 and the ligands can be used as simultaneous pH and metal ion buffers.

Metal Ion Complexation in Aqueous Solution by 5-Thia-2,8-Diazanonane-N,N′-Diacetic Acid

2010 ◽  
Vol 102 (9) ◽  
pp. 593-600 ◽  
Author(s):  
D. M. Wambeke ◽  
W. Lippens ◽  
G. G. Herman ◽  
A. M. Goeminne
Keyword(s):  
Aqueous Solution ◽  
Metal Ion ◽  
Diacetic Acid ◽  
Metal Ion Complexation ◽  
Ion Complexation
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