Novel macrocycle with repeating trazole-carbazole units

Patent metadata

Field	Value
Publication number	US-2016347758-A1
Application number	US-201615170677-A
Country	US
Kind code	A1
Filing date	Jun 1, 2016
Priority date	Jun 1, 2015
Publication date	Dec 1, 2016
Grant date	—

Abstract

Disclosed herein are compositions of tricarbazole triazolophane (tricarb) of Formulas (I), (II) and (III):

wherein R of Formula (I) is selected from a group consisting of alkyl (for example, C 6 -C 18 ), alkyl-substituted phenyl derivatives, and substituted glycol derivatives, among others, or a combination thereof, and R , R ′ and R ″ of Formulas (II) and (III) are independently selected from a group consisting of alkyl (for example, C 6 to C 18 ), alkyl-substituted phenyl derivatives, and substituted glycol derivatives, or a combination thereof. The disclosure presents examples of thin films composed of the same as well as methods of binding anions from the same.

First claim

The invention claimed is:

1 . A composition comprising a tricarbazole triazolophane (tricarb) selected from one of the following:

or a combination thereof,
wherein R of Formula (I) is selected from a group consisting of alkyl (for example, C 6 -C 18 ), alkyl-substituted phenyl derivatives, and substituted glycol derivatives, among others, or a combination thereof, and
R , R ′ and R ″ of Formulas (II) and (III) are independently selected from a group consisting of alkyl (for example, C 6 -C 18 ), alkyl-substituted phenyl derivatives, and substituted glycol derivatives, among others, or a combination thereof.

2 . The composition of claim 1 , wherein R of Formula (I) is selected from a group consisting of C 6 H 13 (IA) C 10 H 21 (IB) C 18 H 37 (IC), di-tert-butyl phenyl (ID) and triethylene glycol (IE), or a combination thereof:

3 . The composition of claim 1 , wherein R is C 10 H 21 (IB):

4 . A complex, comprising:
a composition of claim 1 , and an anion, wherein the composition binds the anion.

5 . The complex of claim 4 , wherein the anion is selected from a group consisting of I − , ClO 4 − , ReO 4 − , PF 6 − , SbF 6 − , FeCl 4 − , mesylate (CH 3 SO 3 − ), triflate (CF 3 SO 3 − ), arsenate (AsO 4 3− ), hexafluoroarsenate (AsF 6 − ), tetrachloroaluminate (AlCl 4 − ), phosphate (PO 4 3− ), hydrogenophosphate (HPO 4 2− ), dihydrogenophosphate (H 2 PO 4 − ), sulfate (SO 4 2− ), hydrogen sulfate (HSO 4 − ), tetracyanoborate (B(CN) 4 − ), a halide (Cl − , Br − , I − ), cyanide, perbromate (BrO 4 − ), periodate (IO 4 − ), fluoride (F − ), bifluoride (HF 2 − ), pertechnetate (TcO 4 − ), monosubstituted phosphate esters (RPO 4 2− ), disubstituted phosphate esters (R 2 PO 4 − ), organosulfonates (RSO 3 − ), thiocyanate, (SCN − ), azide (N 3 − ), triiodide (I 3 − ), carbonate (CO 3 2− ), monohydrogen carbonate (HCO 3 − ), iron tetrachlorate (FeCl 4 − ), gold dicyanate (Au(CN) 2 − ), acetate (CH 3 CO 2 − ), uranium hexafluoride (UF 6 − ), sulfide (S 2− ), platinum hexachlorate (PtCl 6 2− ), and S 2 2− , S 4 2− , S 6 2− , S 8 2− and S n 2− , where n is an even number, or a combination thereof, including mono- and poly-protonated forms (e.g., AsO 4 3− , HAsO 4 2− and H 2 AsO 4 − ), or a combination of the foregoing anions thereof.

6 . The complex of claim 4 , wherein a ratio of the composition comprising a tricarb to the anion in complexes formed therefrom is selected from 1:1 (tricarb:anion), 2:1 (tricarb:anion), 2:2 (tricarb:anion) and 3:2 (tricarb:anion), among others.

7 . The complex of claim 4 , wherein the anion displays one of a binding affinity parameter of log β 2 greater than 7 or a positive cooperativity greater than 5.

8 . A method of binding an anion, comprising:
contacting the anion with a composition of claim 1 .

9 . A method of removing an anion from a mixture, comprising:
contacting the mixture with a composition of claim 1 to form a complex comprising the anion and the composition; and separating the complex from the mixture.

10 . A thin film, comprising a composition of claim 1 .

11 . A method of binding an anion, comprising:
contacting the anion with a thin film of claim 10 .

12 . A method of removing an anion from a mixture, comprising:
contacting the mixture with a thin film comprising the composition of claim 1 to form a complex of the anion and the thin film or a dissociated dimer of a tricarb thereof, wherein the tricarb comprises the composition of claim 1 ; and separating from the mixture the complex of an anion and the thin film or the dissociated dimer of a tricarb thereof.

13 . A method of controlling the thickness of a thin film comprising the composition of claim 1 , wherein the thickness of the thin firm is determined is selected from the group consisting of one of the following parameters:
varying a concentration of the composition of claim 1 , adding anions, and altering at least one substituent of the composition of claim 1 .

14 . The composition of claim 1 , wherein the tricarb can be oxidized.

15 . The complex of claim 6 , wherein the tricarb can be oxidized.

16 . A method of oxidation, comprising contacting the composition of claim 1 with an electrode to which is applied a positive voltage.

17 . A method of oxidation, comprising contacting the complex of claim 6 with an electrode to which is applied a positive voltage.

18 . A method of oxidation, comprising contacting the composition of claim 1 with an oxidizing agent.

19 . A method of oxidation, comprising contacting the complex of claim 6 with an oxidizing agent.

Assignees

• Univ Indiana Res & Tech Corp

Inventors

• Flood Amar
• Hirsch Brandon E
• Lee Semin
• Tait Steven L
• Dobscha James

Classifications

• B01J47/12

  characterised by the use of ion-exchange material in the form of ribbons, filaments, fibres or sheets, e.g. membranes (electrodialysis or electro-osmosis B01D61/42) · CPC title

• C02F2101/12

  Halogens or halogen-containing compounds · CPC title

• B01J20/22

  comprising organic material · CPC title

• B01J45/00

  Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties (ion-exchange chromatography processes B01D15/36) · CPC title

• C02F1/42

  by ion-exchange (ion-exchange in general B01J) · CPC title