Polyanthrylene materials and methods for their preparation and use

• US 8,735,166 B2
• Filed: 04/07/2011
• Issued: 05/27/2014
• Est. Priority Date: 04/07/2011
• Status: Active Grant

• Current Assignee: Tongji University
• Original Assignee: Tongji University
• Inventors: Huang, Mei-rong, Huang, Shao-jun, Li, Xin-gui, Li, Jiang-Ying
• Primary Examiner(s): Menon, Krishnan S
• Assistant Examiner(s): Gerido, Dwan A
• Application Number:
  US13/505,059
• Publication Number:
  US 20120309095A1
• Time in Patent Office: 1,146 Days
• Field of Search: 436/139, 436/140, 528/396
• US Class Current: 436/139
• CPC Class Codes: C08G 2261/314 Condensed aromatic systems, e.g. perylene, anthracene or pyrene
• CPC Class Codes: C08G 2261/43 Chemical oxidative coupling reactions, e.g. with FeCl3
• CPC Class Codes: C08G 61/10 only aromatic carbon atoms, e.g. polyphenylenes
• CPC Class Codes: C08L 65/00 Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain C08L7/00 - C08L57/00, C08L61/00 take precedence; Compositions of derivatives of such polymers
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1416 Condensed systems
• CPC Class Codes: G01N 2021/6417 Spectrofluorimetric devices
• CPC Class Codes: G01N 21/643 non-biological material
• CPC Class Codes: G01N 33/20 Metals
• CPC Class Codes: Y10T 436/21 Hydrocarbon
• CPC Class Codes: Y10T 436/212 Aromatic

Abstract

Compositions containing polyanthrylene and methods of making these compositions are disclosed herein. The polyanthrylene composition can, for example, be used for detection of iron in a sample.

Claims

1. A method of making a copolymer, the method comprising:

forming a mixed solution comprising at least one oxidizing agent, at least one co-catalyst and anthracenes;

maintaining the mixed solution under conditions effective to covalently bond two or more anthracenes to form one or more polyanthrylenes;

wherein the one or more polyanthrylenes form particles; and

isolating the polyanthrylene particles from the mixed solution,

wherein the one or more polyanthrylenes each independently comprises at least two monomer units each independently represented by a formula selected from the group consisting of Formula I, Formula II, Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, Formula XI, Formula XII, Formula XIII, Formula XIV, Formula XV, Formula XVI, Formula XVII, and any combination thereof;

2. The method of claim 1, wherein the co-catalyst is selected from the group consisting of a nitro-alkane, a halogenated alkane, an alkane, and a mixture thereof.

3. The method of claim 1, wherein the maintaining step is performed at a temperature of 10°

C. to 80°

C.

4. The method of claim 1, wherein at least one of the one or more polyanthrylenes has a molecular formula selected from the group consisting of C₄₂H₂₂, C₅₆H₃₀, C₇₀H₂₆, C₁₂₆H₆₈, C₁₄₀H₇₈, and C₁₅₄H₈₄.

5. The method of claim 1, wherein at least 90% by weight of a total amount of aromatic organic compounds in the composition are polyanthrylene.

6. The method of claim 1, wherein the molar ratio of the oxidizing agent to anthracene in the composition is less than or equal to 18:

1.

7. The method of claim 6, wherein the molar ratio of the oxidizing agent to anthracene in the composition is from 7:

1 to 9;

1.

8. The method of claim 1, wherein the oxidizing agent is a Lewis acid.

9. The method of claim 8, wherein the Lewis acid is selected from the group consisting of FeCl₃, AlCl₃—

CuCl₂, TiCl₄, MoCl₅, SbCl₅, AsF₅, and any combination thereof.

10. The method of claim 1, wherein the co-catalyst is selected from the group consisting of CH₃NO₂, CH₂Cl₂, n-Hexane, CH₃CH₂NO₂, CH₃CH₂Cl₂, and a mixture thereof.

11. The method of claim 10, wherein the co-catalyst is CH₃NO₂, CH₂Cl₂, n-hexane, or a mixture thereof.