Methods of producing polyanthracene and uses thereof
View Patent ↗The present application provides methods of producing polyanthracene including polymerization of anthracene monomers in the presence of oxidants and reaction solvents. The present application further provides polyanthracene produced by methods described herein that has higher solubility in organic solvents and better thermal stability and ablation resistance.
1. A method of producing polyanthracene, comprising:
forming a polymerization reaction mixture comprising anthracene monomers, at least one oxidant and at least one reaction solvent,
wherein the anthracene monomers are represented by formula I
maintaining the polymerization reaction mixture under conditions effective to covalently bond two or more anthracene monomers to form one or more polyanthracenes, wherein the weight average molecular weight of the one or more polyanthracenes is no less than 3000 and 5% to 80% of the one or more polyanthracenes by weight contains 18 or more units of anthracene monomers represented by formula I.
2. The method of claim 1 , wherein the oxidant is a Lewis acid.
3. The method of claim 1 , wherein the oxidant is selected from the group consisting of FeCl 3 , FeBr 3 , AlCl 3 , AlBr 3 , AlI 3 , AlRCl 2 , AlR 2 Cl, AlR 3 , CuCl 2 , CuBr 2 , MoCl 5 , SnCl 4 , SnBr 4 , SnI 4 , MgCl 2 , MgBr 2 , MgI 2 , CaCl 2 , CaBr 2 , CaI 2 , ZnCl 2 , ZnBr 2 , ZnI 2 , BF 3 , TiCl 4 , TiBr 4 , SbCl 5 , and any combination thereof.
4. The method of claim 3 , wherein the oxidant is FeCl 3 .
5. The method of claim 1 , wherein the molar ratio of the oxidant to the anthracene monomers ranges from 1:1 to 9:1.
6. The method of claim 1 , wherein the reaction solvent is selected from the group consisting of nitroalkanes, aromatic nitro compounds, hydrocarbons, halogenated hydrocarbons, nitriles, and any combination thereof.
7. The method of claim 1 , wherein the reaction solvent is selected from the group consisting of nitromethane, nitroethane, nitrobenzene, dinitrobenzene, hexane, benzene, pentane, isooctane, cyclohexane, dichloromethane, chloroform, dichloroethane, dichlorobenzene, bromoethane, dibromoethane, bromobenzene, dibromobenzene, bromopentane, carbon tetrachloride, acetonitrile, propionitrile butyronitrile, and any combination thereof.
8. The method of claim 1 , wherein the maintaining step is performed at a temperature ranging from 20 to 100° C.
9. The method of claim 8 , wherein the temperature ranges from 20 to 80° C.
10. The method of claim 9 , wherein the temperature ranges from 20 to 40° C.
11. The method of claim 1 , wherein the polymerization reaction mixture contains water.
12. The method of claim 1 , wherein the maintaining step is performed for 1 to 24 hours.
13. A composition comprising one or more polyanthracenes,
wherein the one or more polyanthracenes are produced by a method comprising:
polymerizing anthracene monomers in the presence of an oxidant and a reaction solvent,
wherein 5% to 80% of the one or more polyanthracenes by weight contains 18 or more units of anthracene monomers.
14. The composition of claim 13 , wherein the thermal decomposition temperature of the one or more polyanthracenes is 400 ° C. or higher in the presence of nitrogen.
15. The composition of claim 13 , wherein the electrical conductivity of the one or more polyanthracenes in nascent state is from 10 −9 to 10 −11 S cm −1 .
16. The composition of claim 13 , wherein the char yield of the one or more polyanthracenes at 1000 ° C. is from 70% to 95%.
17. The composition of claim 13 , wherein 5% to 100% of the one or more polyanthracenes by weight is soluble in an organic solvent.
18. The composition of claim 17 , wherein the organic solvent is selected from the group consisting of N-methylpyrrolidone (NMP), tetrahydrofuran (THF), chloroform, dimethylformamide (DMF), and dimethylsulfoxide (DMSO).
19. The composition of claim 13 , wherein the one or more polyanthracenes have absorbance peaks at wavelengths ranging from 380 nm to 690 nm.
20. The composition of claim 13 , wherein the composition is selected from the group consisting of a thermal resistant material, an ablation resistant material, a carbon precursor, an electrically conductive material, an anti-static electricity material, an anti-ablation paint, a rechargeable battery, an ultra-capacitor, and a carrier for catalysts.