ABSTRACT
Direct (hetero)arylation polymerization (DHAP) has recently been established as an environmentally benign method for the preparation of conjugated polymers. This synthetic tool features the formation of C-C bonds between halogenated (hetero)arenes and simple (hetero)arenes with active C-H bonds, thereby circumventing the preparation of organometallic derivatives and decreasing the overall production cost of conjugated polymers. Since its inception, selectivity and reactivity of DHAP procedures have been improved tremendously through the careful scrutinity of polymerization outcomes and the fine-tuning of reaction conditions. A broad range of monomers, from simple arenes to complex functionalized heteroarenes, can now be readily polymerized. The successful application of DHAP now leads to nearly defect-free conjugated polymers possessing comparable, if not slightly better, characteristics than their counterparts prepared using classical cross-coupling methods. This comprehensive review describes the mechanisms involved in this process from experimental and theoretical standpoints, presents an up-to-date compendium of materials obtained by this means, and exposes its current limitations and challenges.
ABSTRACT
Power conversion efficiency up to 8.6% is achieved for a solution-processed tandem solar cell based on a diketopyrrolopyrrole-containing polymer as the low-bandgap material after using a thin polyelectrolyte layer to modify the electron-transport ZnO layers, indicating that interfacial engineering is a useful approach to further enhancing the efficiency of tandem organic solar cells.
Subject(s)
Electrolytes/chemistry , Pyrroles/chemistry , Solar Energy , Zinc Oxide/chemistry , Electron Transport , Electrons , Metal Nanoparticles/chemistry , Polymers/chemistryABSTRACT
A new alternating copolymer of dithienosilole and thienopyrrole-4,6-dione (PDTSTPD) possesses both a low optical bandgap (1.73 eV) and a deep highest occupied molecular orbital energy level (5.57 eV). The introduction of branched alkyl chains to the dithienosilole unit was found to be critical for the improvement of the polymer solubility. When blended with PC(71)BM, PDTSTPD exhibited a power conversion efficiency of 7.3% on the photovoltaic devices with an active area of 1 cm(2).
Subject(s)
Organosilicon Compounds/chemistry , Polymers/chemistry , Pyrroles/chemistry , Molecular StructureABSTRACT
An efficient route for the synthesis of 1-iodo-5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione as a key intermediate to build new electron-deficient monomers and related conjugated polymers is reported. Along these lines, two new low bandgap copolymers were synthesized from Stille or Suzuki coupling. These polymers were characterized and their properties compared to those of analogous conjugated polymers.