Synthesis of a conjugated pyrrolopyridazinedione–benzodithiophene (PPD–BDT) copolymer and its application in organic and hybrid solar cells

Abstract

Herein, we describe the synthesis and characterization of a conjugated donor–acceptor copolymer consisting of a pyrrolopyridazinedione (PPD) acceptor unit, and a benzodithiophene (BDT) donor unit. The polymerization was done via a Stille cross-coupling polycondensation. The resulting PPD–BDT copolymer revealed an optical bandgap of 1.8 eV and good processability from chlorobenzene solutions. In an organic solar cell in combination with PC70BM, the polymer led to a power conversion efficiency of 4.5%. Moreover, the performance of the copolymer was evaluated in polymer/nanocrystal hybrid solar cells using non-toxic CuInS2 nanocrystals as inorganic phase, which were prepared from precursors directly in the polymer matrix without using additional capping ligands. The PPD–BDT/CuInS2 hybrid solar cells showed comparably high photovoltages and a power conversion efficiency of 2.2%.Graphical abstract

Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties

“…PTz4T-2OD (poly[(1,2,4,5-tetrazin-3,6-diyl)-alt-(3,3′′′-di(2-octyldodecyl)-2,2′;5′,2′′;5′′,2′′′-quaterthiophen-5,5′′′-diyl)]) was synthesized via a Stille cross-coupling polymerization of 2OD-TTz and 5,5′-bis(trimethylstannyl)-2,2′-bithiophene using Pd 2 (dba) 3 as catalyst, as shown in Scheme 2 [ 34 ].

Scheme 2 Synthesis of PTz4T-2OD

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Inverse‐Electron‐Demand Diels–Alder Reactions: Principles and Applications

“…Similar monomers have also been applied to other fields such as organic solar cells. [113] These compounds can be synthesized by first preparing the perquisite tetrazine,w hich is followed by an iEDDA reactionw ith elimination of nitrogen to get the desired diazine electron acceptor.T hese iEDDA reactions are fairly challenging and requiret emperatures of 160 8Ct op roceed. Thisc an be attributed to the electron deficiency of both the dienophile and the diene.…”

“…Pyrrolo[3,4‐ d ]pyridazine‐5,7‐dione 89 , pyrrolophthalazine dione 90 , and pyrroloacenaphthopyridazinedione 91 are typical examples of electron acceptors prepared by our group (Figure ). Similar monomers have also been applied to other fields such as organic solar cells . These compounds can be synthesized by first preparing the perquisite tetrazine, which is followed by an iEDDA reaction with elimination of nitrogen to get the desired diazine electron acceptor.…”

Hot injection synthesis of CuInS2 nanocrystals using metal xanthates and their application in hybrid solar cells

“…From these data it is apparent that the PL quenching is not as efficient as for nanocomposite layers containing CuInS 2 nanocrystals prepared in situ in the conjugated polymer matrix. 27,52,53 A possible reason for the non-complete quenching of the photoluminescence of the polymer in the films might be polymer domains in the nanocomposite layer in which the polymer is not well blended with the CuInS 2 nanocrystals. 46 This assumption is corroborated by the AFM images (see Fig.…”