High photostabilization of Zn2+ chelating spironaphthoxazine

Kim, Sung-Hoon; Wang, Sheng; Ahn, Chi-Hee; Choi, Myung-Shik

doi:10.1007/bf02875837

Cited by 11 publications

(8 citation statements)

References 21 publications

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“…No spectral change was observed in the SNO solutions containing Mg 2+ or Zn 2+ even during UV irradiation, although metal chelation was observed in the aprotic polar solvents [7,8,18,19]. This is because the hydrogen bonding to ethanol molecules prevents the chelation.…”

Section: Reaction During Uv Irradiationmentioning

confidence: 99%

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Photochromic behavior of spironaphthoxazine in metal ion-containing solutions

Nishikiori

Takamura

Shimamura

et al. 2011

Journal of Photochemistry and Photobiology A: Chemistry

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The isomerization and metal chelation of spironaphthoxazine (SNO) in ethanol solutions have been investigated by measuring the UV-vis absorption spectra as a function of time.The protonated species of merocyanine (MC), an isomer of SNO, was gradually formed in the solutions containing SNO and aluminum ions in the dark. The proton was provided by the reaction of the aluminum ions with a slight amount of water contained in the ethanol solvent.The protonated species was slowly transformed into the aluminum chelate complex of MC by ligand exchange of the ethanol-solvated aluminum for MC in the dark. UV irradiation promoted the isomerization and chelation without forming the protonated species. The spectroscopic analysis with various compositional ratios of SNO and aluminum ions revealed that one aluminum ion was coordinated to three bidentate MC ligands in the ethanol solution.

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Section: Reaction During Uv Irradiationmentioning

confidence: 99%

“…This process can be regarded as a first-order reaction because the rate of the aluminum chelation is much faster than that of the ring-opening isomerization to form MC [7,18].…”

Section: Reaction During Uv Irradiationmentioning

confidence: 99%

Photochromic behavior of spironaphthoxazine in metal ion-containing solutions

Nishikiori

Takamura

Shimamura

et al. 2011

Journal of Photochemistry and Photobiology A: Chemistry

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“…complex is observed at around 540 nm by UV irradiation of SNO in aprotic polar solvents, such as acetone and acetonitrile, in the presence of Zn 2+ [8,9,18,19]. The MC-Zn 2+ complex was not observed in ethanol because the MC form was stabilized by hydrogen bonding to the solvent molecules [20].…”

Section: +mentioning

confidence: 99%

Chelation ability of spironaphthoxazine with metal ions in silica gel

Nishikiori

Teshima

Fujii

2012

Photochem Photobiol Sci

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“…In some instances, the ring-opening reaction may also be induced in the dark through the addition of particular metal cations that are able to coordinate to the phenolate oxygen atom and/or other additional coordinating atoms and substituents that have been introduced into the structure of the spirooxazine and spiropyran derivatives [17][18][19][20][21][22][23][24][25][26]. Regardless of whether the ring-opening reaction is induced by cations or irradiation, the coordination of metal ions to the substrate usually results in a negative photochromism, i.e., a blue shift of the absorption maximum of the merocyanine form [5,19,[27][28][29], and increased stability of the latter towards the thermal back reaction [21,28,[30][31][32][33][34]. In this context, the complexation of metal cations has also been exploited to utilize this compound class for the development of photochromic chemosensors that allow the colorimetric or fluorimetric detection of particular analytes [5,29,[35][36][37][38][39][40][41].…”

Section: Introductionmentioning

confidence: 99%

Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates

Pithan¹,

Ihmels²

2020

Beilstein J. Org. Chem.

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Two new spiroindolinonaphthoxazine derivatives with an electron-accepting styrylquinolizinium or styrylcoralyne unit, respectively, were synthesized, and the influence of such an arylvinyl substituent on the chemical and photochemical properties of the compounds was investigated. Specifically, these spirooxazines turned out to be resistant towards the photoinduced merocyanine formation, and the irradiation with light mainly led to photodegradation of the substrates. However, it was shown by colorimetric and fluorimetric screening assays as well as by detailed NMR spectroscopic and mass spectrometric studies that the addition of particular metal ions (Cu2+, Fe3+, and to a certain extent Hg2+) initially induced a ring-opening reaction that was irreversibly followed by a fast ring closure–deprotonation–oxidation sequence to give styryl-substituted naphthoxazole derivatives as the products quantitatively. For the quinolizinium-substituted spirooxazine derivative, the formation of the respective oxidation product caused the development of a broad absorption band between 425 nm and 500 nm and a new emission band at λfl = 628 nm, so that it may be employed as a selective chemosensor or chemodosimeter for the colorimetric and fluorimetric detection of Cu2+ and Fe3+.

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High photostabilization of Zn2+ chelating spironaphthoxazine

Cited by 11 publications

References 21 publications

Photochromic behavior of spironaphthoxazine in metal ion-containing solutions

Photochromic behavior of spironaphthoxazine in metal ion-containing solutions

Chelation ability of spironaphthoxazine with metal ions in silica gel

Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates

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