Regioregular copolymers and methods for making same

1. A method for making a compound, the method comprising:

combining a silylalkynyl dialkoxyl arylaldehyde and a X-substituted dialkoxyl arylphosphonate; and

contacting the silylalkynyl dialkoxyl arylaldehyde and the X-substituted dialkoxyl arylphosphonate under conditions that provide for coupling of the silylalkynyl dialkoxyl arylaldehyde and the X-substituted dialkoxyl arylphosphonate to provide a X-substituted silylalkynyl diarylethene,

wherein X is selected from the group consisting of hydroxide, alkoxide, astatine, iodine, bromine, chlorine, fluorine, triflate (CF 3 SO 3 − ), mesylate (CH 3 SO 3 − ), tosylate (CH 3 C 6 H 4 SO 3 − ) and besylate (C 6 H 5 SO 3 − ).

2. The method of claim 1 , wherein the silylalkynyl dialkoxyl arylaldehyde is selected from the group consisting of Formula I or Ia:

wherein:

each R 1a and R 2a is, independently, C 1 -C 20 alkyl, C 2 -C 20 alkene or alkylene glycol; and

each R 5 is C 1 -C 20 alkyl.

3. The method of claim 1 , wherein the X-substituted dialkoxyl arylphosphonate comprises a compound of Formula II:

wherein:

each R 1b and R 2b is, independently, alkyne C 1 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne or alkylene glycol;

each R 3 and R 4 is, independently, C 1 -C 20 alkyl.

4. The method of claim 1 , wherein the X-substituted silylalkynyl diarylethene comprises a compound of Formula III:

wherein:

each R 1a , R 1b , R 2a , and R 2b is, independently, C 1 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne or alkylene glycol;

R 5 is C 1 -C 20 alkyl.

5. The method of claim 1 , further comprising:

placing the X-substituted silylalkynyl diarylethene under conditions that allow the silyl moiety to be removed from the X-substituted silylalkynyl diarylethene to provide a X-substituted alkynyl diarylethene; and

placing the X-substituted alkynyl diarylethene under conditions that allow X-substituted alkynyl diarylethenes are coupled to provide the regioregular aryl ethynyl-aryl vinyl copolymer.

6. The method of claim 5 , wherein the regioregular aryl ethynyl-aryl vinyl copolymer comprises a compound of Formula IV:

wherein:

each R 1a , R 1b , R 2a , and R 2b , independently, comprise C 1 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne, or alkylene glycol; and n comprises an integer from 2 to 100.

7. The method of claim 6 , wherein R 1a and R 1b are the same and R 2a and R 2b are the same.

8. The method of claim 1 , further comprising contacting a silyl-alkynyl with an X-substituted dialkoxyl arylaldehyde under conditions that allow the silyl-alkynyl and X-substituted dialkoxyl arylaldehyde to react to provide the silylalkynyl dialkoxyl arylaldehyde.

9. The method of claim 8 , wherein the silyl-alkynyl is selected from the group consisting of trimethylsilyl acetylene, tert-butyldimethylsilyl acetylene, tri-iso-propylsilyloxymethyl acetylene, and tri-iso-propylsilyl acetylene, or combinations thereof.

10. The method of claim 8 , further comprising contacting a C 1 -C 6 alkoxy dihalide C 1 -C 6 alkane with an unprotected X-substituted dialkoxyl arene under conditions that allow the C 1 -C 6 alkoxy dihalide C 1 -C 6 alkane and the unprotected X-substituted dialkoxyl arene to react to provide the X-substituted dialkoxyl arylaldehyde.

11. The method of claim 10 , wherein the X-substituted dialkoxyl arylaldehyde comprises a compound of Formula V:

wherein:

each R 1a , R 1b , R 2a , and R 2b , independently, comprise C 1 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne or alkylene glycol.

12. The method of claim 10 , further comprising contacting a hydroxylated C 1 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne, or alkylene glycol and an unprotected X-substituted monoalkoxyl para-substituted arene under conditions that allow the hydroxylated C 1 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne, or alkylene glycol and the unprotected X-substituted monoalkoxyl para-substituted arene to react to provide the unprotected X-substituted dialkoxyl arene.

13. The method of claim 10 , wherein hydroxylated C 2 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne, or alkylene glycol and the halogenated C 2 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne, or alkylene glycol comprise different C 1 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne, or alkylene glycol moieties.

14. The method of claim 1 , further comprising contacting a phosphonate containing compound and an X-substituted dialkoxyl arylaldehyde under conditions that allow the phosphonate containing compound and the X-substituted dialkoxyl arylaldehyde to react to provide the X-substituted dialkoxyl arylphosphonate monomer.

15. The method of claim 14 , wherein contacting the phosphonate containing compound and the X-substituted dialkoxyl arylaldehyde comprises:

placing the X-substituted dialkoxyl arylaldehyde under conditions that allow the X-substituted dialkoxyl arylaldehyde to be reduced to provide a X-substituted dialkoxyl arylmethanol;

combining the X-substituted dialkoxyl arylmethanol with a leaving group containing compound under conditions that allow the leaving group containing compound to react with the X-substituted dialkoxyl arylmethanol to provide a X-substituted dialkoxyl arylmethyl-leaving group;

combining the X-substituted dialkoxyl arylmethyl-leaving group with a phosphite containing compound under conditions that allow the X-substituted dialkoxyl arylmethyl-leaving group with a phosphite containing compound to react; and

allowing an Arbuzov rearrangement to occur to provide the X-substituted dialkoxyl arylphosphonate monomer.

16. A method for producing a monomer, the method comprising:

providing a monoalkoxyl para-substituted arene according to Formula VI

wherein

R 6 is selected from the group consisting of C 1 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne and alkylene glycol; and

R 7 is selected from the group consisting of H, C 1 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne and alkylene glycol;

placing the monoalkoxyl para-substituted arene under conditions that allow a protecting group to be introduced at a non-alkylenated substituent of the monoalkoxyl para-substituted arene to provide a protected monoalkoxyl para-substituted arene;

placing the protected monoalkoxyl para-substituted arene under conditions that allow the protected monoalkoxyl para-substituted arene to be halogenated to provide a protected X-substituted monoalkoxyl arene

wherein X is selected from the group consisting of hydroxide, alkoxide, astatine, iodine, bromine, chlorine, fluorine, triflate (CF 3 SO 3 − ), mesylate (CH 3 SO 3 − ), tosylate (CH 3 C 6 H 4 SO 3 − ) and besylate (C 6 H 5 SO 3 − )

placing the protected X-substituted monoalkoxyl arene under conditions that allow the protecting group to be removed from the protected X-substituted monoalkoxyl arene to provide an unprotected X-substituted monoalkoxyl arene;

placing the unprotected X-substituted monoalkoxyl arene under conditions that allow an aldehyde to be introduced onto the unprotected X-substituted monoalkoxyl arene to provide a X-substituted arylaldehyde; and

placing the X-substituted arylaldehyde under conditions that allow a silylalkynyl to be introduced onto the X-substituted arylaldehyde to provide a silylalkynyl arylaldehyde.

17. The method of claim 16 , further comprising combining a hydroxylated C 1 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne, or alkylene glycol and an unprotected X-substituted monoalkoxyl arene under conditions that allow the hydroxylated C 1 -C 20 alkyl, C 2 C 20 alkene, C 2 -C 20 alkyne, or alkylene glycol and the unprotected X-substituted monoalkoxyl arene to react to provide the unprotected X-substituted dialkoxyl arene.

18. The method of claim 16 , further comprising placing the X-substituted arylaldehyde conditions that allow a phosphonate to be introduced onto the X-substituted arylaldehyde to provide a X-substituted arylphosphonate.

19. The method of claim 18 , wherein placing the X-substituted arylaldehyde conditions that allow a phosphonate to be introduced comprises:

placing the X-substituted arylaldehyde under conditions that allow the X-substituted arylaldehyde to be reduced to provide a X-substituted arylmethanol;

placing the X-substituted arylmethanol under conditions that allow a leaving group to be introduced onto the X-substituted arylmethanol to provide a X-substituted arylmethyl-leaving group;

placing the X-substituted arylmethyl-leaving group under conditions that allow the leaving group to be substituted of the X-substituted arylmethyl-leaving group with a phosphite; and

allowing an Arbuzov rearrangement to occur to provide a X-substituted arylphosphonate.

20. The method of claim 19 , further comprising:

placing the X-substituted silylalkynyl diarylethene under conditions that allow the silyl to be removed to provide X-substituted alkynyl diarylethene; and

contacting the X-substituted diarylethene alkynyl diarylethene under conditions that allow the X-substituted diarylethene alkynyl diarylethene to be coupled to provide a regioregular poly(aryl ethynyl)-poly(aryl vinyl).

21. The method of claim 16 , further comprising combining the silylalkynyl arylaldehyde and the X-substituted arylphosphonate under conditions that allow the silylalkynyl arylaldehyde and the X-substituted arylphosphonate to react to create a X-substituted silylalkynyl diarylethene.

22. The method of claim 16 , further comprising:

providing a para-substituted arene and a halogenated C 1 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne, or alkylene glycol; and

contacting the para-substituted arene and the halogenated C 1 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne, or alkylene glycol under conditions that allow the para-substituted arene and the halogenated C 1 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne, or alkylene glycol to react to provide a monoalkoxyl para-substituted arene.