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Band-gap engineering of donor – Acceptor-substituted pi-conjugated polymers
Three series of alternating donor- acceptor-substituted co-oligomers (with different chain lengths) have been prepared by application of the Pd-catalyzed Stille coupling methodology. They contain pyrrole or thiophene as the electron-rich unit and quinoxaline or 2,1,3-benzothiadiazole as the electron-deficient unit. The trimethylstannyl group is always located on the electron-rich unit, whereas the bromo substituent is always located on the electron-deficient one. The tBoc-protecting group is used in the synthesis of the pyrrole-containing oligomers. The incremental bathochromic shift of lambda(max) upon chain elongation of the three series of oligomers is less than that of the homooligomers of thiophene and pyrrole; this decrease is caused by a diminished dispersion of the LUMO level upon chain elongation. This conclusion was drawn after comparing the oxidation and reduction behavior of the thiophene/benzothiadiazote co-oligomers with that of thiophene oligomers. The incremental bathochromic shift is similar for all three series of oligomers and is used as a tool in the band-gap engineering of donor- acceptor-substituted pi-conjugated polymers.
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Reference：
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2048 | ChemSpider