Synthetic receptors for hydrosulfide

Patent metadata

Field	Value
Publication number	US-2022082544-A1
Application number	US-202117536994-A
Country	US
Kind code	A1
Filing date	Nov 29, 2021
Priority date	Jun 3, 2016
Publication date	Mar 17, 2022
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 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.

2 . The compound of claim 1 , wherein Y is

and R 50 is halogen and R 51 is hydrogen.

3 . The compound of claim 1 , wherein Y is

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

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

5 . 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 are each independently selected from H, substituted lower alkyl, lower alkyl, substituted aralkyl, aralkyl, substituted aryl or aryl; or
(B)(ii) 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.

6 . The device of claim 5 , wherein Y is

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.

7 . The device of claim 5 , wherein the polymer is selected from at least one of a polyvinyl chloride, polyvinyl alcohol, polystyrene, butadiene copolymer, polysiloxane, epoxy acrylate, methacrylate, urethane acrylate, polyacrylamide, or a combination thereof.

8 . The device of claim 5 , wherein the polymeric element further comprises at least one ionophore.

9 . The device of claim 8 , wherein the ionophore comprises at least one tetralkylammonium salt.

10 . The device of claim 5 , wherein the compound (B)(i) or the compound (B)(ii) is present in the polymeric element in an amount of 0.1 to 5% by weight, based on the total weight of the polymeric element.

11 . 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 locationally 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 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.

12 . The device of claim 11 , wherein the reversible, non-covalent bonding involves hydrogen bonding.

13 . The device of claim 12 , wherein the hydrogen bonding includes a C—H . . . S hydrogen bond.

14 . The device of claim 11 , wherein the at least one moiety is a CH hydrogen bond donor.

Assignees

• Univ Oregon

Inventors

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

Classifications

• 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

• Y10T436/156666

  Sulfur containing · CPC title

• 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

• G01N33/182 Primary

  Specific anions in water · CPC title