Solvent-dependent conformational and fluorescence change of an N-phenylbenzohydroxamic acid derivative bearing two pyrene moieties

The conformation of N-phenylbenzohydroxamic acid has been reported to change depending on the solvent properties. Here, we newly synthesized N-phenylbenzohydroxamic acid derivative, which contains two pyrene moieties separated from the phenyl rings by ethylene linkers. It showed solvent-dependent co...

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Bibliographic Details
Published in:Tetrahedron 2012-04, Vol.68 (13), p.2778-2783
Main Authors: Kanai, Misae, Hirano, Tomoya, Azumaya, Isao, Okamoto, Iwao, Kagechika, Hiroyuki, Tanatani, Aya
Format: Article
Language:English
Subjects:
Aromatic amide
Chemistry
Condensed benzenic and aromatic compounds
Conformational alteration
Derivatives
Ethylene
Exact sciences and technology
Fluorescence
Fluorescence spectroscopy
Monomers
Organic chemistry
Phenyls
Preparations and properties
Pyrene
Pyrenes
Solvents
Tetrahedrons
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Summary:The conformation of N-phenylbenzohydroxamic acid has been reported to change depending on the solvent properties. Here, we newly synthesized N-phenylbenzohydroxamic acid derivative, which contains two pyrene moieties separated from the phenyl rings by ethylene linkers. It showed solvent-dependent conformational change, and its fluorescence was also solvent-dependent, that is, only monomer fluorescence of pyrene was observed in DMSO or DMF, whereas the excimer fluorescence was observed in CH2Cl2 or CHCl3. Thus, the structural characteristics could be converted to fluorescence change as output, which would be a good candidate as a fluorescent sensor. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.02.012