Carbon nanohoops and methods of making
View Patent ↗The present invention provides cycloparaphenylene compounds, their macrocyclic precursors, and methods for making the compounds. The cycloparaphenylene compounds can be used to prepare armchair carbon nanotubes.
1. A compound of formula II:
wherein
each R 1 is independently selected from the group consisting of hydrogen, C 1-6 alkyl, C 1-6 heteroalkyl, C 3-8 cycloalkyl, heterocycloalkyl, aryl and heteroaryl; and
subscript m is an integer from 2 to 10.
2. The compound of claim 1 , wherein each R 1 is C 1-6 alkyl.
3. The compound of claim 1 , wherein each R 1 is methyl.
4. The compound of claim 1 , wherein subscript m is an integer selected from the group consisting of 3, 4 and 6.
5. The compound of claim 1 , wherein
each R 1 is methyl; and
subscript m is an integer selected from the group consisting of 3, 4 and 6.
6. A method of preparing a compound of formula IIa:
wherein
each R 1 is independently selected from the group consisting of hydrogen, C 1-6 alkyl, C 1-6 heteroalkyl, C 3-8 cycloalkyl, heterocycloalkyl, aryl and heteroaryl,
each dashed line is optionally a bond, and
subscript m is an integer from 2 to 10, the method comprising:
contacting a plurality of compounds of formula IIIa:
wherein
each R 2 is independently selected from the group consisting of a halogen and a boronate,
thereby preparing the compound of formula IIa.
7. The method of claim 6 , wherein the contacting step comprises at least one compound of formula IIIa where each R 2 is a halogen and at least one compound of formula IIIa where each R 2 is a boronate.
8. The method of claim 6 , wherein the contacting step comprises a plurality of compounds where one R 2 is a halogen and one R 2 is a boronate.
9. The method of claim 6 , wherein each dashed line is a bond.
10. The compound of claim 1 , wherein subscript m is an integer from 3 to 10.
11. The method of claim 6 , wherein subscript m is an integer from 3 to 10.