Synthetic receptors for hydrosulfide

Patent metadata

Field	Value
Publication number	US-2017350870-A1
Application number	US-201715612848-A
Country	US
Kind code	A1
Filing date	Jun 2, 2017
Priority date	Jun 3, 2016
Publication date	Dec 7, 2017
Grant date	—

Abstract

A method for detecting for the presence of H 2 S or HS − anion in a system, comprising contacting a sample from the system with a compound, or a protonate or salt thereof, having a structure represented by:

wherein Y represents an aromatic group or a substituted aromatic group;
n is 1 or 2;
R is independently H, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, amido, aryloxy, cyano, hydroxyl, or sulfonyl;
R 1 is H, substituted lower alkyl, lower alkyl, substituted aralkyl or aralkyl;
R 2 is selected from H, acyl, substituted aralkyl, aralkyl, phosphonyl, —SO 2 R 3 ; —C(O)R 5 ; —C(O)OR 7 or —C(O)NR 9 R 10 ;
R 3 ; R 5 ; R 7 ; R 9 and R 10 are each independently selected from H, substituted lower alkyl, lower alkyl, substituted aralkyl, aralkyl, substituted aryl or aryl.

First claim

What is claimed is:

1 . A method for detecting for the presence of H 2 S or an anionic sulfide species in a system, comprising contacting a sample from the system with a compound, or a protonate or salt thereof, having a structure represented by:

wherein Y represents an aromatic group or a substituted aromatic group;
n is 1 or 2;
R is independently H, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, amido, aryloxy, cyano, hydroxyl, or sulfonyl;
R 1 is H, substituted lower alkyl, lower alkyl, substituted aralkyl or aralkyl;
R 2 is selected from H, acyl, substituted aralkyl, aralkyl, phosphonyl, —SO 2 R 3 ; —C(O)R 5 ; —C(O)OR 7 or —C(O)NR 9 R 10 ;
R 3 ; R 5 ; R 7 ; R 9 and R 10 are each independently selected from H, substituted lower alkyl, lower alkyl, substituted aralkyl, aralkyl, substituted aryl or aryl.

2 . A method for detecting for the presence of H 2 S or an anionic sulfide species in a system, comprising contacting a sample from the system with a compound, or a protonate or salt thereof, having a structure represented by:

wherein Y represents a substituted aromatic group or an aromatic group;
each R 15 is independently H, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, amido, aryloxy, cyano, hydroxyl, or sulfonyl;
each X is independently halogen, alkoxy, substituted alkoxy, alkyl, substituted alkyl or a polyether moiety; and
m is 0 to 5.

3 . The method of claim 1 , wherein the system comprises an aqueous system.

4 . The method of claim 2 , wherein the system comprises an aqueous system.

5 . The method of claim 1 , wherein the system comprises a biological system.

6 . The method of claim 2 , wherein the system comprises a biological system.

7 . The method of claim 1 , wherein Y is selected from:

wherein R 20 , R 50 , R 51 , R 52 , R 53 , R 54 and R 55 are each independently selected from hydrogen, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, aryloxy, cyano, hydroxyl, or sulfonyl.

8 . The method of claim 7 , wherein Y is

wherein R 50 is halogen.

9 . The method of claim 7 , wherein Y is

wherein R 20 is hydrogen.

10 . The method of claim 2 , wherein Y is selected from:

wherein R 20 , R 50 , R 51 , R 52 , R 53 , R 54 and R 55 are each independently selected from hydrogen, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, aryloxy, cyano, hydroxyl, or sulfonyl.

11 . The method of claim 10 , wherein Y is

wherein R 50 is halogen.

12 . The method of claim 10 , wherein Y is

wherein R 20 is hydrogen.

13 . A method for detecting for the presence of H 2 S or an anionic sulfide species in a system, comprising contacting a sample from the system with a compound, or a protonate or salt thereof, having a structure that includes at least one moiety configured for reversible, non-covalent binding of the anionic sulfide species.

14 . The method of claim 13 , wherein the reversible, non-covalent bonding involves hydrogen bonding.

15 . The method of claim 14 , wherein the hydrogen bonding includes a C—H . . . S hydrogen bond.

16 . The method of claim 13 , wherein the at least one moiety is a CH hydrogen bond donor.

17 . A compound, or a protonate or salt thereof, having a structure represented by:

wherein Y is

each R 15 is independently H, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, amido, aryloxy, cyano, hydroxyl, or sulfonyl;
each X is independently halogen, alkoxy, substituted alkoxy, alkyl, substituted alkyl or a polyether moiety;
m is 0 to 5; and
wherein R 50 , R 51 , R 52 , R 53 , R 54 and R 55 are each independently selected from hydrogen, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, aryloxy, cyano, hydroxyl, or sulfonyl.

18 . The compound of claim 17 , wherein Y is

and R 50 is halogen and R 51 is hydrogen.

19 . The compound of claim 17 , wherein Y is

and R 52 , R 53 , R 54 and R 55 are each hydrogen.

20 . The compound of claim 17 , wherein each R 15 is alkyl; m is 1, and X is alkoxy.

21 . A device comprising:
a source; a drain; a gate; a bulk layer, wherein the source contacts a first portion of the bulk, and the drain contacts a second portion of the bulk that is physically distinct from the first portion and the gate is disposed on a surface of the bulk in a position between the source and the drain forming a gate/bulk interface; and a polymeric element disposed on a surface of the gate that opposes the gate/bulk interface, wherein the polymeric element comprises a (A) polymer and (B)(i) a compound, or a protonate or salt thereof, having a structure represented by:

wherein Y represents an aromatic group or a substituted aromatic group;
n is 1 or 2;
R is independently H, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, amido, aryloxy, cyano, hydroxyl, or sulfonyl;
R 1 is H, substituted lower alkyl, lower alkyl, substituted aralkyl or aralkyl;
R 2 is selected from H, acyl, substituted aralkyl, aralkyl, phosphonyl, —SO 2 R 3 ; —C(O)R 5 ; —C(O)OR 7 or —C(O)NR 9 R 10 ;
R 3 ; R 5 ; R 7 ; R 9 and R 10

Assignees

• Univ Oregon

Inventors

• Haley Michael M
• Pluth Michael
• Johnson Darren W
• Fontenot Sean

Classifications

• C07C275/34

  having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring · CPC title

• C07D213/40

  Acylated substituent nitrogen atom · CPC title

• G01N33/0044 Primary

  Sulphides, e.g. H2S · CPC title

• C07C275/28

  having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton · CPC title

• G01N27/414

  Ion-sensitive or chemical field-effect transistors, i.e. ISFETS or CHEMFETS · CPC title