Synthesis and fluorescent properties of 2-(1H-benzimidazol-2-yl)-phenol derivatives

  • Ouyang J
  • Ouyang C
  • Fujii Y
 et al. 
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Abstract

A high yield one pot synthesis of 2-(2-hydroxyaryl)-1H-benzimidazole derivs. from 2-hydroxy arom. aldehydes with arom. 1,2-diamines in the presence of manganese(III) acetate at room temp. was developed. Nine fluorescent 2-(2-hydroxyaryl)-1H-benzimidazoles and two fluorescent 2-(2-hydroxyaryl)-1H-naphth[2,3-d]imidazoles Cl were prepd. in 38-87% yield and the UV absorption and fluorescent spectra of the eleven compds. synthesized were detd. in methanol. The fluorescent characteristics of the 2-(2-hydroxyaryl)benzimidazole derivs. prepd. were investigated on the basis of an excited-state intramol. proton transfer mechanism, Stokes shift, quantum yield, and the relationship between fluorescent intensity and the substituents were derived. [on SciFinder (R)]

Author-supplied keywords

  • Cyclocondensation reaction catalysts (in prepn. of
  • Fluorescence
  • Fluorescent indicators (prepn. and fluorescent pro
  • Hydrogen bond
  • Proton transfer (intramol.
  • Protonation (photochem.
  • Rotamers (in fluorescent benzimidazolylphenols)
  • Substituent effects (on fluorescence of benzimidaz
  • Tautomers (keto-enol
  • UV and visible spectra (of fluorescent benzimidazo
  • in fluorescent benzimidazolylphenols)

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Authors

  • Jie Ouyang

  • Chenguang Ouyang

  • Yuki Fujii

  • Yoshiharu Nakano

  • Takuji Shoda

  • Tetsuo Nagano

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