Decomposable s-tetrazine based polymers for single walled carbon nanotube applications

Patent metadata

Field	Value
Publication number	US-2018195997-A1
Application number	US-201715708855-A
Country	US
Kind code	A1
Filing date	Sep 19, 2017
Priority date	Jan 9, 2017
Publication date	Jul 12, 2018
Grant date	—

Abstract

A process for purifying semiconducting single-walled carbon nanotubes (sc-SWCNTs) extracted with a conjugated polymer, the process comprising exchanging the conjugated polymer with an s-tetrazine based polymer in a processed sc-SWCNT dispersion that comprises the conjugated polymer associated with the sc-SWCNTs. The process can be used for production of thin film transistors and chemical sensors. In addition, disclosed herein is use of an s-tetrazine based polymer for purification of semiconducting single-walled carbon nanotubes (sc-SWCNTs).

First claim

We claim:

1 . A chemical sensor for detection of one or more chemicals in the ppt to ppb range, the sensor made by a process comprising the steps of:
a) applying a dispersion of a sc-SWCNT/s-tetrazine based conjugated polymer composite to a substrate; b) applying heat and/or UV light to decompose the s-tetrazine based conjugated polymer; and c) removing the resulting decomposition products.

2 . The chemical sensor of claim 1 , wherein the sensor has a lower detection limit of from 4 ppt to 100 ppb.

3 . The chemical sensor of claim 2 , wherein the sensor has a lower detection limit of from 3 ppt to 1 ppb.

4 . The chemical sensor of claim 1 , wherein the one or more chemicals is in a gaseous phase or a liquid phase.

5 . The chemical sensor of claim 4 , wherein the one or more chemicals is gaseous ammonia or gaseous nitrogen dioxide (NO 2 ).

6 . The chemical sensor of claim 1 , wherein the s-tetrazine based polymer has the following structure:

where A is O, S, Se or C═C; n is an integer from 1 to 4; R 1 is independently H, F, CN or a C1-C20 linear or branched aliphatic group; Ar is one or more substituted or unsubstituted aromatic units; and, m is an integer 5 or greater.

7 . The chemical sensor of claim 1 , wherein the s-tetrazine based polymer is PBDTFTz:

8 . The chemical sensor of claim 1 , wherein the s-tetrazine based polymer is PDTSTTz:

9 . The chemical sensor of claim 1 , wherein the s-tetrazine based polymer is:

and wherein: R 1 and R 2 =2-ethylhexyl; or R 1 =2-ethylhexyl and R 2 =hexyl; or R 1 =hexyl and R 2 =2-ethylhexyl; or R 1 and R 2 =hexyl; or R 1 =methyl and R 2 =2-ethylhexyl.

10 . The chemical sensor of claim 1 , wherein the s-tetrazine based polymer is PCPDTFTz:

in which Ar=cyclopenta[2,1-b;3.4-b′]dithiophene.

11 . (canceled)

12 . The chemical sensor of claim 1 , wherein the conjugated polymer comprises a polyfluorene or a polythiophene.

13 . (canceled)

14 . The chemical sensor of claim 1 , wherein the conjugated polymer is poly(9,9-di-n-dodecylfluorene) (PFDD).

15 . The chemical sensor of claim 1 , wherein the weight ratio of the conjugated polymer to the sc-SWCNTs has a maximum value of 5.

16 . (canceled)

17 . (canceled)

18 . A process for producing a chemical sensor that detects one or more chemicals in the ppt to ppb range, the process comprising:
a) applying a dispersion of a sc-SWCNT/s-tetrazine based conjugated polymer composite to a substrate; b) applying heat and/or UV light to decompose the s-tetrazine based conjugated polymer; and c) removing the resulting decomposition products.

19 . The process of claim 18 , wherein the sensor has a lower detection limit of from 4 ppt to 100 ppb.

20 . (canceled)

21 . (canceled)

22 . The process of claim 18 , wherein the one or more chemicals is gaseous ammonia or gaseous nitrogen dioxide (NO 2 ).

23 . The process of claim 18 , wherein the s-tetrazine based polymer has the following structure:

where A is O, S, Se or C═C; n is an integer from 1 to 4; R 1 is independently H, F, CN or a C1-C20 linear or branched aliphatic group; Ar is one or more substituted or unsubstituted aromatic units; and, m is an integer 5 or greater.

24 . The process of claim 18 , wherein the s-tetrazine based polymer is PBDTFTz:

25 . The process of claim 18 , wherein the s-tetrazine based polymer is PDTSTTz:

26 . (canceled)

27 . The process of claim 18 , wherein the s-tetrazine based polymer is PCPDTFTz:

in which Ar=cyclopenta[2,1-b;3.4-b′]dithiophene.

28 . (canceled)

29 . The process of claim 18 , wherein the conjugated polymer comprises a polyfluorene or polythiophene.

30 . (canceled)

31 . (canceled)

32 . (canceled)

33 . (canceled)

34 . (canceled)

35 . A chemical sensor for detection of gaseous ammonia or gaseous nitrogen dioxide in the ppt to ppb range, the sensor comprising a network of semiconducting single-walled carbon nanotubes (sc-SWCNTs).

36 . The chemical sensor of claim 35 , wherein the sensor has a lower detection limit of from 4 ppt to 100 ppb.

37 . The chemical sensor of claim 36 , wherein the sensor has a lower detection limit of from 3 ppt to 1 ppb.

Assignees

• Nat Res Council Canada

Inventors

• Li Zhao
• Ding Jianfu
• Malenfant Patrick Roland Lucien

Classifications

• C08G2261/19

  partially conjugated · CPC title

• C08G61/125

  with a five-membered ring containing one oxygen atom in the ring · CPC title

• G01N27/4146

  involving nanosized elements, e.g. nanotubes, nanowires · CPC title

• C08G2261/94

  Applications in sensors, e.g. biosensors · CPC title

• C08G2261/73

  Depolymerisation · CPC title