A simple and efficient route to N-functionalized dithieno[3,2-b:2',3'-d]pyrroles: fused-ring building blocks for new conjugated polymeric systems.
A general synthetic route has been developed for the simple and efficient preparation of N-functionalized dithieno[3,2-b:2',3'-d]pyrroles. These synthetic methods utilize N-functionalized N-(3'-thienyl)-3-aminothiophenes produced from the Pd-catalyzed amination of 3-bromothiophene with primary amines, followed by a one-pot bromination/cyclization process. This combination allows the convenient preparation of a variety of N-functionalized dithieno[3,2-b:2',3'-d]pyrroles (where substituent = hexyl, octyl, decyl, tert-butyl, and p-hexylphenyl) in good yield (65-82%). Characterization of the structure and reactivity of this class of compounds is also described, including electrochemical and photophysical data for all compounds and X-ray structural data for the octyl-, tert-butyl-, and p-hexylphenyl-functionalized compounds.
Ogawa
Katsu
K
Department of Chemistry, North Dakota State University, Fargo, North Dakota 58105-5516, USA.
Rasmussen
Seth C
SC
D000588:Amines / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D018360:Crystallography, X-Ray; D003500:Cyclization; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry* / Q000302:isolation & purification*; D011108:Polymers / Q000737:chemistry; D011758:Pyrroles / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D013876:Thiophenes / Q000737:chemistry
D000588:Amines; D011108:Polymers; D011758:Pyrroles; D013876:Thiophenes; D010165:Palladium