(Mechano)synthesis of azomethine- and terpyridine-linked diketopyrrolopyrrole-based polymers

Abstract

Three efficient synthetic approaches towards new azomethine- and terpyridine-containing 2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (diketopyrrolopyrrole, DPP) based polymers, such as P1 and P2, are reported. The first approach involves the Pd-catalyzed synthesis via two- or three-component Suzuki or Stille cross-coupling reaction in solution. The second approach involves Pd-catalyzed Suzuki cross-coupling reaction under ball-milling conditions. And, finally, the third approach involves Pd-free condensation reaction under ball-milling conditions. The newly obtained polymers exhibited absorbance around 700 nm and emission around 900 nm, and, thus, these polymers are considered to be NIR-fluorophores.

TM-Free and TM-Catalyzed Mechanosynthesis of Functional Polymers

“…We recently reported on the mechanosynthesis of diketo-pyrrolopyrroles (DPPs)based azomethine polymers [52] (Figure 5). Two synthetic strategies were used.…”

“…Regarding future perspectives, one can mention the following. Among the TMcatalyzed mechanochemical approaches to producing functional polymers, Pd-catalyzed processes, which have been widely explored for small molecules [180], have so far only been reported by a few cases of Suzuki cross-coupling reactions [52,84,85,98]. So, in the near future, one might expect the interest in mechanopolymerization reactions based on the Buchwald, Stille, or Sonogashira cross-coupling protocols to grow.…”