Modular synthesis of graphene nanoribbons and graphene substructures from oligo-alkynes

1. A method of cyclizing a compound, the method comprising:

contacting the compound with Bu 3 SnH, wherein the compound comprises repeat units having the following structure (I):

wherein:

n is an integer having a value of at least three and less than 25;

Ra 1 , Ra 2 , Ra 3 , and Ra 4 are each carbon; and R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted aliphatic moiety, and a substituted or unsubstituted alkoxy; wherein the substituents of substituted aliphatic moiety are selected from the group consisting of chlorine, bromine, amino, and cyano;

or, alternatively, R A1 , R A2 , R A3 , and R A4 are each carbon; R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of hydrogen and a substituted or unsubstituted aliphatic moiety; wherein the substituents of substituted aliphatic moiety are selected from the group consisting of chlorine, bromine, amino, and cyano; and any two adjacent R A1 , R A2 , R A3 , and R A4 and the R 1 , R 2 , R 3 , and R 4 , respectively bonded thereto together with the atoms to which they are bonded complete naphthalene or anthracene;

T 1 and T 2 are each independently selected from the group consisting of hydrogen, an aliphatic moiety having from 1 to 18 carbon atoms; an aromatic moiety having from three to 18 carbon atoms; an alkoxy moiety having from 1 to 6 carbon atoms; and a cyano moiety; and

further wherein at least one of the repeat units comprises an R 1 moiety having the structure (II):

wherein:

Y is selected from the group consisting of bromine, iodine, and xanthyl; and

Z is selected from the group consisting of O, S, S(O), SO 2 , CH 2 , and NCH 3 .

2. The method of claim 1 wherein n has a value between four and 25.

3. The method of claim 1 wherein the compound has the following structure (III):

wherein n has a value between four and 25;

R 1 , R 2 , R 3 , R 4 , T 1 , and T 2 are as defined in claim 1 ; and

further wherein at least one of the repeat units comprises an R 1 moiety having the structure (II):

wherein Y and Z are as defined in claim 1 .

4. The method of claim 1 wherein the compound has the following structure (VIII):

wherein R 1 , R 2 , R 3 , R 4 , T 1 , T 2 , Y, and Z are as defined in claim 1 .

5. The method of claim 4 wherein the compound has a structure selected from the group consisting of structure (VIIIa), structure (VIIIb), structure (VIIIc), and structure (VIIId):

6. The method of claim 1 wherein the compound has the following structure (IX):

wherein R 1 , R 2 , R 3 , R 4 , T 1 , T 2 , Y, and Z are as defined in claim 1 .

7. The method of claim 1 wherein the compound has the following structure (Xa):

wherein R 2 , R 3 , Y, and Z are as defined above in connection with claim 1 .