Dianhydrides, polyimides, methods of making each, and methods of use

1. A composition, comprising:

an aromatic dianhydride having the following structure:

wherein each R 1 , R 2 , and R 4 are independently selected from the group consisting of: a linear or branched, substituted or unsubstituted, alkyl group, wherein Ar 2 is selected from the group consisting of: an aryl group, a polyaromatic group, and a heteroaryl group where each are substituted or unsubstituted.

2. The composition of claim 1 , wherein Ar 2 is selected from:

substituted or unsubstituted, and wherein R 5 and R 7 are independently selected from a linear or branched, substituted or unsubstituted, alkyl group.

3. A composition, comprising:

a polymide having the following structure:

wherein Y is selected from an aryl group a polyaromatic group, or a heteroaryl group, wherein x is 1 to 10,000, wherein R is selected from the following structures:

wherein each of R 1 , R 2 , and R 4 are independently selected from the group consisting of: a linear or branched, substituted or unsubstituted alkyl group, wherein Ar 2 is selected from the group consisting of: an aryl group, a polyaromatic group, and a heteroaryl group where each can be substituted or unsubstituted.

4. A composition, comprising:

a polyimide having the following structure:

wherein Y is selected from an aryl group a polyaromatic group, or a heteroaryl group, wherein x is 1 to 10,000, wherein R is selected from the following structures:

wherein each of R 1 , R 2 , and R 4 are independently selected from the group consisting of: a linear or branched, substituted or unsubstituted alkyl group, wherein Ar 2 is selected from the group consisting of: an aryl group, a polyaromatic group, and a heteroaryl group where each can be substituted or unsubstituted, and

wherein Ar 2 is selected from

substituted or unsubstituted, and wherein R 5 and R 7 are independently selected from a linear or branched, substituted or unsubstituted, alkyl group.

5. The composition of claim 3 , wherein Y is selected from the group consisting of:

6. A composition, comprising:

a polyimide having the following structure:

wherein Ar 3 and Ar 4 are independently selected from an aryl group a polyaromatic group, or a heteroaryl group, wherein m and n are independently 0 to 10,000, wherein R is selected from the following structures:

wherein R 1 , R 2 , and R 4 are independently selected from the group consisting of: a linear or branched, substituted or unsubstituted alkyl group, wherein Ar 2 is selected from the group consisting of: an aryl group, a polyaromatic group, and a heteroaryl group, wherein R 5 is a linear or branched, substituted or unsubstituted alkyl group.

7. The composition of claim 6 , wherein Ar 3 and Ar 4 are different and m and n are 1 to 10,000.

8. A composition, comprising:

a polyimide having the following structure:

wherein Ar 3 and Ar 4 are independently selected from an aryl group a polyaromatic group, or a heteroaryl group, wherein m and n are independently 0 or 10,000, wherein R is selected from the following structures:

wherein R 1 , R 2 , and R 4 are independently selected from the group consisting of: a linear or branched, substituted or unsubstituted alkyl group, wherein Ar 2 is selected from the group consisting of: an aryl group, a polyaromatic group, and a heteroaryl group, wherein R 5 is a linear or branched, substituted or unsubstituted alkyl group, and

wherein Ar 3 and Ar 4 are each independently selected from the group consisting of:

9. A method of making an aromatic dianhydride, comprising:

wherein A includes N-bromosuccinimide, wherein B includes sodium nitrite, wherein C includes copper cyanide, wherein D includes potassium hydroxide followed by acetic anhydride, wherein R is selected from the following structures;

wherein R 1 , R 2 , and R 4 are independently selected from the group consisting of: a linear or branched, substituted or unsubstituted alkyl group, wherein Ar 2 is selected from the group consisting of: an aryl group, a polyaromatic group, and a heteroaryl group where each is substituted or unsubstituted.

10. The method of claim 9 , wherein Ar 2 is selected from:

substituted or unsubstituted, and wherein R 5 and R 7 are independently selected from a linear or branched, substituted or unsubstituted, alkyl group.

11. A method for making a polyimide, comprising: reacting an aromatic dianhydride with a multi-amine to form a polyimide, wherein the aromatic dianhydride has the following structure:

wherein each R 1 , R 2 , and R 4 are independently selected from the group consisting of: a linear or branched, substituted or unsubstituted, alkyl group, wherein Ar 2 is selected from the group consisting of: an aryl group, a polyaromatic group, and a heteroaryl group where each are substituted or unsubstituted.

12. The method of claim 11 , wherein the multi-amine is selected from the group consisting of a diamine, a triamine, a tetramine, and an amine having 5 or more amino groups.

13. The method of claim 11 , wherein the multiamine is selected from the group consisting of: