Fluorescent sensor for metal cation detection based on 2-(2′-hydroxyphenyl)benzazole containing a Schiff base moiety

Patent metadata

Field	Value
Publication number	US-9891237-B2
Application number	US-201414340084-A
Country	US
Kind code	B2
Filing date	Jul 24, 2014
Priority date	Jul 24, 2013
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

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.

First claim

What is claimed is:

1. 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 first Schiff base moiety; and

a second ligand group selected from the group consisting of a second Schiff base moiety and a hydroxyl group, where the first Schiff base moiety and the second Schiff base moiety may be the same or different, and at least one of the first Schiff base moiety and the second Schiff base moiety is defined by the formula

where R 9 is a hydrogen atom or a monovalent organic group, and R 10 is a monovalent organic group that includes an atom with a lone pair of electrons.

2. The hydroxyphenylbenzazole compound containing a Schiff base moiety of claim 1 , where the benzazole group is a benzoxazole group.

3. The hydroxyphenylbenzazole compound containing a Schiff base moiety of claim 1 , where the benzazole group is a benzothiazole group.

4. The hydroxyphenylbenzazole compound containing a Schiff base moiety of claim 1 where the benzazole group is a benzimidazole group.

5. The hydroxyphenylbenzazole compound containing a Schiff base moiety of claim 1 , where at least one of the first Schiff base moiety and the second Schiff base moiety is a Schiff base selected from the group consisting of:

6. The hydroxyphenylbenzazole compound containing a Schiff base moiety of claim 1 , where the hydroxyphenylbenzazole compound containing a Schiff base moiety 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; Y 7 is the first Schiff base moiety, and R 1 , R 2 , R 3 , R 4 , R 5 , and R 8 are each individually a hydrogen atom or a monovalent organic group.

7. The hydroxyphenylbenzazole compound containing a Schiff base moiety of claim 1 , where the hydroxyphenylbenzazole compound containing a Schiff base moiety 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; Y 1 and Y 3 are each individually a Schiff base moiety, and R 2 , R 4 , R 5 , R 6 , R 7 , and R 8 are each individually a hydrogen atom or a monovalent organic group.

8. The hydroxyphenylbenzazole compound containing a Schiff base moiety of claim 1 , where the hydroxyphenylbenzazole compound containing a Schiff base moiety 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; Y 6 and Y 8 are each individually a Schiff base moiety, and R 1 , R 2 , R 3 , R 4 , R 5 , and R 7 are each individually a hydrogen atom or a monovalent organic group.

9. 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; Y 6 , Y 7 , and Y 8 are each individually a hydrogen atom, a Schiff base moiety, or a hydroxyl group, R 1 , R 2 , R 3 , R 4 , and R 5 are each individually a hydrogen atom or a monovalent organic group; with the proviso that at least one of Y 6 , Y 7 , and Y 8 is a Schiff base moiety defined by the formula

where R 9 is a hydrogen atom or a monovalent organic group, and R 10 is a monovalent organic group that includes an atom with a lone pair of electrons.

10. A method for detecting the presence of metal ions, comprising the steps of:
(a) contacting a test sample with 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 first Schiff base moiety; and

a second ligand group selected from the group consisting of a second Schiff base moiety and a hydroxyl group, where the first Schiff base moiety and the second Schiff base moiety may be the same or different, and at least one of the first Schiff base moiety and the second Schiff base moiety is defined by the formula

where R 9 is a hydrogen atom or a monovalent organic group, and R 10 is a monovalent organic group that includes an atom with a lone pair of electrons
(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.

11. The method of claim 10 , where the hydroxyphenylbenzazole compound containing a Schiff base moiety 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; Y 7 is the first Schiff base moiety, and R 1 , R 2 , R 3 , R 4 , R 5 , and R 8 are each individually a hydrogen atom or a monovalent organic group.

12. The method of claim 11 , where the hydroxyphenylbenzazole compound containing a Schiff base moiety is used to detect a zinc ion, and the observation of a near-infrared response indicates the detection of zinc.

13. The method of claim 10 , where the hydroxyphenylbenzazole compound containing a Schiff base moiety 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; Y 1 and Y 3 are each individually a Schiff base moiety, and R 2 , R 4 , R 5 , R 6 , R 7 , and R 8 are each individually a hydrogen atom or a monovalent organic group.

14. The method of claim 13 , where the hydroxyphenylbenzazole compound containing a Schiff base moiety is used to detect the presence of a metal cation selected from Fe 3+ , Cr 3+ , and Al 3 +.

15. The method of claim 10 , where the hydroxyphenylbenzazole compound containing a Schiff base moiety 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; Y 6 and Y 8 are each individually a Schiff base moiety, and R 1 , R 2 , R 3 , R 4 , R 5 , and R 7 are each individually a hydrogen atom or a monovalent organic group.

16. The method of claim 15 , where the hydroxyphenylbenzazole compound containing a Schiff base moiety is used to detect the presence of a metal cation selected from Fe 3 +, Cr 3 +, and Al 3 +.

17. The method

Assignees

• Pang Yi
• Wang Junfeng
• Univ Akron

Inventors

• Pang Yi
• Wang Junfeng

Classifications

• C07D413/14

  containing three or more hetero rings · CPC title

• C07D413/12

  linked by a chain containing hetero atoms as chain links · CPC title

• G01N33/84 Primary

  involving inorganic compounds or pH · CPC title