Low band gap copolymer containing naphthalene-1,4,5,8-tetracarboxylic bisimide: Synthesis, properties and organic solar cell applications

A new alternating donor–acceptor copolymer, poly{[2,7-(9,9′-dioctylfluorene)-alt-5,5′-(bis(2,2′-thiophene)-4,7-(2,1,3-benzothiadiazole)]-co-[2,7-(9,9′-dioctylfluorene)-alt-5,5′-(bis(2,2′-thiophene)-2,6-naphthalene-1,4,5,8-tetracarboxylic-N,N′-di(2-ethylhexyl)imide]} (PFTBTN), was synthesized for the use of photovoltaic cells. The copolymer containing fluorene, as the donor segment and naphthalene bisimide, dithienylbenzothiadiazole, as the acceptor segment was polymerized via Suzuki couplings to achieve a polymer with a narrow band gap. The band gap values of the copolymer film determined from optical and electrochemical measurements were 1.69 and 2.06 eV, respectively. The optical absorption spectrum revealed two broad bands in the range of 300–750 nm. Electrochemical studies indicate sufficiently deep HOMO/LUMO levels that enable a high open-circuit voltage when fullerene derivative ([6,6]-phenyl-C61 butyric acid methyl ester) was used as an electron acceptor. Bulk heterojunction photovoltaic cells were fabricated in the device configuration of ITO/PEDOT:PSS/PFTBTN:PCBM/TiOx/Al. Open-circuit voltage reached 0.74 V with the maximum energy conversion efficiency of 0.40% under the illumination of AM 1.5 (100 mW/cm2).

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► Novel copolymers based on fluorene, naphthalene bisimide, and dithienylbenzothiadiazole.
► Incorporation of dithienylbenzothiadiazole increase the LUMO and the charge transfer.
► Copolymer exhibits two broad absorption bands in the range of 300–750 nm.
► PFTBTN shows small optical band gap with 1.69 eV.