Deactivation of electronic excitation in the 2-(o-hydroxyphenyl)-benzoxalone molecule

Stryukov, M. B.; Lyubarskaya, A. E.; Knyazhanskii, M. I.

doi:10.1007/bf00605550

Cited by 4 publications

(7 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Dramatic fluorescence enhancement of 3 with magnesium cation may be interpreted by the formation of a complex 5 (X ) O, M n+ ) Mg 2+ ), where the benzoxazole and phenolate rings lie on the same plane by the bridging magnesium cation, and this coplanarity and the anionic property of the phenolate ring bring about large fluorescence enhancement. 16 The formation of the coplanar anion type of 3 is supported by the red-shifted absorption (λ ab ) 359 nm), 6,8,12,13 excitation of which also results in the same fluorescence enhancement (Figure 8). The curve fitting of the fluorescence intensity according to the Benesi-Hildebrand plot supported the formation of a 1:1 complex of 3 and magnesium cation, its binding constant being estimated to be K ) 5.4 × 10 3 M -1 in methanol (Figure 9).…”

Section: Resultsmentioning

confidence: 86%

“…Spectral changes caused by the concentration and the polarity of the solvent point out that under the polar environment 3 or 4 equilibrates with its phenolate anion, which emits the intermediate wavelength fluorescence and absorbs at longer wavelength. ,, A larger fluorescence quantum yield of 3 than 4 supports the formation of 3 (anion) in preference to that of 4 (anion) in methanol. To understand the ease of formation of 3 (anion), ab initio calculations were performed for the ground states of the anions of 3 and 4 .…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Application of 2-(3,5,6-Trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole and -benzothiazole to Fluorescent Probes Sensing pH and Metal Cations

et al. 2001

View full text Add to dashboard Cite

2-(3,5,6-Trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole (3) and benzothiazole analogue (4) are prepared by the two-step procedures from the corresponding 2-(pentafluorophenyl)benzazoles. Benzoxazole 3 is applicable to a fluorescent probe sensing magnesium cation, and 4 is suitable for sensing zinc cation. Both fluorophores 3 and 4 are sensitive to the pH change at pH 7-8, resulting in large fluorescence enhancement under basic conditions. Their high sensitivity to pH and selectivity in metal cations are ascribed to the high acidity of the fluorophenol moiety.

show abstract

Section: Resultsmentioning

confidence: 86%

Section: Resultsmentioning

confidence: 99%

Application of 2-(3,5,6-Trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole and -benzothiazole to Fluorescent Probes Sensing pH and Metal Cations

et al. 2001

View full text Add to dashboard Cite

show abstract

“…The HPBO-based functional materials can undergo excited-state intramolecular proton transfer (ESIPT, as shown in Figure) by the structural transformation between the enol (X1) and keto tautomers (X2) . The ESIPT of the HPBO could result in a large Stokes shift ranging from 100 to 500 nm.…”

Section: Introductionmentioning

confidence: 99%

2-(2′-Hydroxyphenyl)benzoxazole-Containing Two-Photon-Absorbing Chromophores as Sensors for Zinc and Hydroxide Ions

et al. 2008

View full text Add to dashboard Cite

Three new two-photon-absorbing (2PA) chromophores derived from 2-(2′-hydroxyphenyl)benzoxazole (HPBO), having two-photon absorption cross sections up to 530 GM (δ, expressed in GM; 1 GM ) 1 × 10 -50 cm 4 s photon -1 molecule -1 ), were synthesized and investigated as metal ion and pH sensors. These chromophores were designed with an increasing number (0, 1, and 2) of HPBO(s) groups as binding sites for metal ions. Such variations provide a systematic approach to correlate structures with their linear photophysical, sensing, and two-photon absorption properties. The HPBO-containing sensors show unique response for zinc ion. Significant zinc ion stimulated photophysical properties with evident enhancements in fluorescence intensities from both one-and two-photon processes were detected. Moreover, one chromophore having HPBO groups in both terminal ends exhibits significant modulation of fluorescence intensities in response to the phenol group deprotonation in the HPBO moiety. A very large two-photon absorption cross section of 4120 GM, the highest reported for bisphenolate-containing 2PA materials, was measured for the chromophore under basic conditions. The molecular structures have a significant influence on the 2PA properties, which follows a trend of the substitution groups on the HPBO moiety in the order of -O -> -OZn > -OCH 2 R. The present study provides a protocol for elucidating the relationship between the photophysical properties and molecular structures.

show abstract

“…The weak UV fluorescence (λ max = 370 nm) was attributed to the enolic form a, whereas the fluorescence in the visible region (λ max = 440 nm) is emitted by the bipolar structure b. The fluorescence with anomalous Stokes shift was attributed to structures with a hydrogen atom covalently bonded with the nitrogen atom [in a polar solvent λ max = 490 nm (b), in a nonpolar solvent λ max = 520 nm (c)] [120,121].…”

Section: Luminescent Characteristicsmentioning

confidence: 98%

Aryl and 1,3-dioxoindanyl derivatives of azoles and azines (review)

Гарновский

Sennikova

2007

Chem Heterocycl Comp

View full text Add to dashboard Cite

Data on the synthesis, tautomerism, complexing characteristics, and luminescence of 2- (2′-amino-, hydroxy-, hydrochalcogenophenyl)azoles, azines, and hetarylindanediones are reviewed.This review is devoted to the recent chemistry of five-and six-membered nitrogen-containing heterocycles containing 2-amino-, 2-hydroxy-, and 2-hydrochalcogenophenyl and indanedione (thione) fragments. These compounds are of fundamental importance during the investigation of fundamental problems in the chemistry of heterocyclic compounds -synthesis, tautomerism in heteroaromatic systems [1][2][3][4], their complexing characteristics [5], and their valuable properties [6][7][8].

show abstract

Deactivation of electronic excitation in the 2-(o-hydroxyphenyl)-benzoxalone molecule

Cited by 4 publications

References 2 publications

Application of 2-(3,5,6-Trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole and -benzothiazole to Fluorescent Probes Sensing pH and Metal Cations

Application of 2-(3,5,6-Trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole and -benzothiazole to Fluorescent Probes Sensing pH and Metal Cations

2-(2′-Hydroxyphenyl)benzoxazole-Containing Two-Photon-Absorbing Chromophores as Sensors for Zinc and Hydroxide Ions

Aryl and 1,3-dioxoindanyl derivatives of azoles and azines (review)

Contact Info

Product

Resources

About