A conjugated polymer is described here that possesses main-chain donor/acceptor repeat units separated by aryl passivating units. This donor/acceptor/passivator (DAP) polymer was constructed of sequential electron-rich N,N ‘-dimethyl-3,4-diaminothiophene, electron-deficient 3,4-dinitrothiophene, and passivating phenylene repeat units via Stille coupling reactions. Several new transformations were conducted on thiophene cores in order to construct the monomer units: tert -butoxycarbonyl (Boc) amine protections, selective monostannylations, selective monodebrominations, lithium tetramethylpiperidide (LTMP) induced lithiation on nitrothiophenes, and selective stannylations using Bu 3 SnSnBu 3 /Pd on phenylene iodides over thienyl bromides. The Stille polymerization afforded the Boc-protected DAP polymer that was characterized at this stage. ZnCl 2 -catalyzed Boc removal afforded the desired DAP polymer; however, its insolubility curtailed detailed investigations of the properties.
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Devasagayaraj et al. (1999) studied this question.
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