Novel fluorescent sensor for metal cation detection based on 2-(2'-hydroxyphenyl)benzazole containing a schiff base moiety
AssigneeThe University of Akron
InventorsYi Pang, Junfeng Wang
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Abstract
Hydroxyphenylbenzazole compounds that are useful for the selective detection of zinc, aluminum, chromium, and iron cations in vitro and in vivo. The Hydroxyphenylbenzazole compounds include a 2-hydroxyphenyl group bound to a single benzazole group; a first ligand group that is a Schiff base moiety; and a second ligand group selected from a Schiff base moiety and a hydroxyl group
Claims20
A hydroxyphenylbenzazole compound containing a Schiff base moiety, the compound comprising:
- a 2-hydroxyphenyl group bound to a single benzazole group;
- a first ligand group that is a Schiff base moiety;
- and
- a second ligand group selected from a Schiff base moiety and a hydroxyl group.
A method for detecting the presence of metal ions, comprising the steps of:
- (a) contacting a test sample with hydroxyphenylbenzazole compound containing a Schiff base moiety the compound comprising:
- a 2-hydroxyphenyl group bound to a benzazole group;
- a first ligand group that is a Schiff base moiety;
- and
- a second ligand group selected from a Schiff base moiety and a hydroxyl group;
- (b) exciting the hydroxyphenylbenzazole compound containing a Schiff base moiety with an excitation wavelength to induce a fluorescence response;
- and
- (c) observing a fluorescence response emission.
A hydroxyphenylbenzazole compound containing a Schiff base defined by the formula
- where X is an oxygen atom, a sulfur atom, a nitrogen atom with a pendant hydrogen atom, or a nitrogen atom with a pendant alkyl group;
- Y6, R7, and Y8 are each individually a hydrogen atom, a Schiff base moiety, or a hydroxyl group with the proviso that at least one of Y6, R7, and Y8 is a Schiff base moiety, and R1, R2, R3, R4, and R5 are each individually a hydrogen atom or a monovalent organic group.
A method of preparing a hydroxyphenylbenzazole compound containing a Schiff base comprising:
- (a) reacting an aldehydephenylbenzazol compound with a compound that includes and amino or hydrazine moiety;
- where the aldehydephenylbenzazol compound is defined by the formula
- where X is an oxygen atom, a sulfur atom, a nitrogen atom with a pendant hydrogen atom, or a nitrogen atom with a pendant alkyl group;
- A1, A3, A6, A7, and A8 are each individually a hydrogen atom, an aldehyde group, or an ester group, with the proviso that at least one of A1, A3, A6, A7, and A8 is a aldehyde group;
- R11 is a monovalent organic group;
- and R2, R4, and R5 are each individually a hydrogen atom or a monovalent organic group.
Dependencies are inferred from the claim text.