A Facile Synthesis of Low-Band-Gap Donor-Acceptor Copolymers Based on Dithieno[3,2-b:2 `,3 `-d]thiophene

TitleA Facile Synthesis of Low-Band-Gap Donor-Acceptor Copolymers Based on Dithieno[3,2-b:2 `,3 `-d]thiophene
Publication TypeJournal Article
Year of Publication2011
AuthorsS.Y. Ku, C.D. Liman, Daniel J. Burke, N.D. Treat, J.E. Cochran, E. Amir, Louis A. Perez, M.L. Chabinyc, and C.J. Hawker
JournalMACROMOLECULES
Volume44
Pagination9533-9538
Date PublishedDEC 27
ISSN0024-9297
AbstractA facile and scalable synthetic route to a soluble dithieno[3,2-b:2',3'-d]thiophene (DTT) unit has been developed, which utilizes a Stile coupling reaction to efficiently synthesize the bisthienyl sulfide intermediate. This simplifies the overall DTT synthesis to only four steps with a 44% yield and facilitates its use as a donor unit in low-band-gap polymers. Solution processable alternating D-pi-A-pi polymers (DTTBTO and DTTDPP) have been synthesized with DTT as the donor unit and either a benzothiodiazole derivative (BTO) or fused ring 1,4-diketopyrrolo[3,4-c]pyrrole (DPP) serving as the acceptor unit. The ability to tailor the structure of these donor-acceptor systems permits a detailed understanding of structure/property relationships for band-gap engineering, absorbance, V(oc), and efficiency to be developed and applied to the design of high-performance organic solar cells.
DOI10.1021/ma202095j