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US 8,168,671 B2Granted
Synthesis of thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds and their derivatives and use thereof
AssigneeUniversity of Connecticut
InventorGregory A. Sotzing
Life of this patent
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Abstract
Inexpensive and facile methods of preparing fused heterocycles such as thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds, and their derivatives are disclosed. Also disclosed are regioregular polymers prepared from the fused heterocycles.
Claims20
A method of making a fused heterocycle, comprising:
- carboxylating the 3 position of a compound of formula I or a suitably protected derivative thereof
- to form a dicarboxylic acid compound;
- and
- converting the dicarbocylic acid compound to a fused heterocycle of formula (II)
- wherein X1 is S, O, N—R1, or P—R2, wherein R1 is hydrogen or a nitrogen protecting group, and R2 is hydrogen or a phosphorus protecting group;
- X2 is S, O, N—R1, or P—R2 where R1 and R2 are as previously defined;
- and
- R is hydrogen, C1-C20 alkyl, C1-C20 haloalkyl, aryl, heteroaryl, C1-C20 alkoxy, C1-C20 haloalkoxy, aryloxy, —C1-C10 alkyl-O—C1-C10 alkyl, —C1-C10 alkyl-O-aryl, nitro, halo, amino, or mono- or di alkyl amino.
5 more elements
A regioregular polymer, comprising:
- a regioregular fused heterocycle polymer of formula (III)
- wherein X1 is S, O, N—R1 or P—R2, wherein R1 is hydrogen or a nitrogen protecting group, and R2 is hydrogen or a phosphorus protecting group;
- X2 is S, O, N—R1, or P—R2 where R1 and R2 are as previously defined;
- and
- R is C1-C20 alkyl, C1-C20 haloalkyl, aryl, heteroaryl, C1-C20 alkoxy, C1-C20 haloalkoxy, aryloxy, —C1-C10 alkyl-O—C1-C10 alkyl, —C1-C10 alkyl-O-aryl, nitro, halo, amino, or mono- or di alkyl amino.
2 more elements
Dependencies are inferred from the claim text.