Naphthalene-containing polymers and methods of making the same

1. A dimer comprising:

a first hydroxyl-functionalized naphthalene group; and

a second hydroxyl-functionalized naphthalene group, wherein:

the first hydroxyl-functionalized naphthalene group and the second hydroxyl-functionalized naphthalene group are connected by a bridging group.

2. The dimer of claim 1 , wherein the bridging group comprises an aliphatic group.

3. The dimer of claim 1 , wherein the dimer has a structure selected from the group consisting of

and wherein R is the bridging group.

4. The dimer of claim 3 , wherein the structure is selected from the group consisting of

5. The dimer of claim 3 , wherein the structure is selected from the group consisting of

6. A polymer comprising:

a dimer comprising:

a first hydroxyl-functionalized naphthalene group; and

a second hydroxyl-functionalized naphthalene group, wherein:

the first hydroxyl-functionalized naphthalene group and the second hydroxyl-functionalized naphthalene group are connected by a bridging group, wherein:

the polymer contains between 2 and 1500 units of the dimer, and

the bridging group comprises an aliphatic group.

7. The polymer of claim 6 , wherein the polymer has a structure selected from the group consisting of

wherein R is the bridging group and n is the number of units of the dimer.

8. The polymer of claim 7 , wherein the structure is selected from the group consisting of

9. The polymer of claim 8 , wherein the structure is selected from the groups consisting of

10. The polymer of claim 7 , wherein the polymer is endcapped with at least one of a hydroxyl group, a halogen, an amine, or an oxygenated aromatic.

11. The polymer of claim 6 , wherein the polymer has a structure selected from the group consisting of

wherein n is the number of units of the dimer.

12. The polymer of claim 6 , further comprising a weight averaged molecular weight, M W , between 3 kDa and 400 kDa.

13. The polymer of claim 6 , further comprising a degradation temperature between 150° C. and 500° C.

14. The polymer of claim 6 , further comprising a glass transition temperature, T g , between 50° C. and 200° C.

15. A method comprising:

reacting a precursor molecule with a first bridging molecule to form a dimer, wherein:

the precursor molecule comprises a hydroxyl-functionalized naphthalene, and

the first bridging molecule comprises at least one of a ketone, an aldehyde, or a halogenated aliphatic molecule.

16. The method of claim 15 , wherein the second bridging molecule comprises at least one of a carbonate or a phosgene.

17. The method of claim 15 , wherein:

the first bridging molecule has the structure

R 1 comprises a first aliphatic group, and

R 2 comprises a second aliphatic group.

18. The method of claim 15 , further comprising:

polymerizing the dimer with a second bridging molecule to produce a polymer, wherein:

the second bridging molecule has the structure

and

X comprises at least one of a hydroxyl group, a halogen, an amine, or an oxygenated aromatic.

19. The method of claim 16 , wherein the precursor molecule comprises at least one of a naphthol, methyl naphthalene, an ethyl naphthalene, a dimethyl naphthalene, a methyl naphthol, or a dimethyl naphthol.

20. A method for producing a dimer, the method comprising:

reacting 2-naphthol with Br 2 to produce 6-bromonaphthalen-2-ol;

reacting the 6-bromonaphthalen-2-ol to produce 2-bromo-6-methoxynaphthalene;

reacting the 2-bromo-6-methoxynaphthalene with magnesium to produce 6-methoxynaphthalene, 2-MgBr;

reacting the 6-methoxynaphthalene, 2-MgBr with 2,3-dibromobutane to produce 2,2′-(1,2-dimethyl-1,2-ethanediyl)di-(6-methoxynaphthalene); and

reacting the 2,2′-(1,2-dimethyl-1,2-ethanediyl)di-(6-methoxynaphthalene) to produce the dimer comprising 6,6′-(butane-2,3,-diyl)di(naphthalen-2-ol).