Application of 2-(3,5,6-trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole and -benzothiazole to fluorescent probes sensing pH and metal cations.
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.
Tanaka
K
K
Faculty of Engineering, Seikei University, Musashino-shi, Tokyo 180-8633, Japan. tanaka@ge.seikei.ac.jp
Kumagai
T
T
Aoki
H
H
Deguchi
M
M
Iwata
S
S
D052160:Benzothiazoles; D001583:Benzoxazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015374:Biosensing Techniques; D002412:Cations / Q000032:analysis; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008670:Metals / Q000032:analysis*; D015335:Molecular Probes / Q000138:chemical synthesis / Q000737:chemistry; D013057:Spectrum Analysis; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015032:Zinc / Q000032:analysis
C449081:2-(3,5,6-trifluoro-2-hydroxy-4-methoxyphenyl)benzothiazole; C449080:2-(3,5,6-trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole; D052160:Benzothiazoles; D001583:Benzoxazoles; D002412:Cations; D005456:Fluorescent Dyes; D008670:Metals; D015335:Molecular Probes; D013844:Thiazoles; C005465:benzothiazole; D015032:Zinc