A regioregular polythiophene–fullerene for polymeric solar cells

Abstract

In this article, we present the synthesis and characterization of a new thiophenic copolymer bearing the C 60 fullerene directly linked to the end of a hexamethylenic side chain. This copolymer was prepared with good yield using a simple and straightforward post-polymerization functionalization procedure applied on a soluble regioregular polymeric precursor obtained by regiospecific organometallic coupling. Copolymer structural and photophysical properties were investigated by gel permeation chromatography, thermal analysis (DSC and TGA), NMR, IR, UV-Vis, and atomic force spectroscopy. The double-cable copolymer possesses good solubility in common organic solvents, high filmability, thermal stability, and low segmental aggregation tendency. It was tested as a photoactive layer in a polymeric solar cell showing a power conversion efficiency under 100 mW cm 22 AM 1.5 illumination higher than 4%, more than that of the reference cell made with the conventionally used P3HT/PCBM blend.

Brush Polymer of Donor-Accepter Dyads via Adduct Formation between Lewis Base Polymer Donor and All Carbon Lewis Acid Acceptor

“…With macromers P3HT-(CH 2 ) 3 -MIM and P3HT-(CH 2 ) 3 -VIM in hand, we envisioned that they could be conveniently converted into linked P3HT-C 60 donor-acceptor dyads ( Scheme 2 ), an interesting topic of current investigations into photoinduced intramolecular energy transfer and electron transfer within such systems [ 32 , 33 , 34 , 35 , 36 , 47 ]. The proposed two-step procedure to construct such dyads, P3HT-(CH 2 ) 3 -MIM-C 60 and P3HT-(CH 2 ) 3 -VIM-C 60 , first involves deprotonation of the imidazolium chain end to generate the corresponding NHC moiety, followed by facile adduct formation between the polymeric NHC LB and all carbon LA C 60 , a method we established previously for the construction of poly(NHC-C 60 ) [ 41 ].…”

“…Several strategies have been employed to control the morphology of the donor P3HT/acceptor C 60 composite and thus optimize the device performance, such as thermal annealing [ 27 ], solvent treatment [ 28 , 29 ], blending [ 30 , 31 ], and inclusion of chemical reaction [ 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ] to bond them together. There are several chemical reactions that have been explored to covalently link C 60 to P3HT, for example, Vilsmeier-Haack reaction [ 32 , 33 ], Grignard-coupling reaction [ 34 ], Bingel reaction [ 35 ], lithiated reaction [ 36 ], and copolymerization with C 60 -containing monomer [ 37 , 38 ]. In this context, the facile reaction between a bulky N -heterocyclic carbene (NHC) and C 60 that leads to the instantaneous formation of a thermally stable zwitterionic Lewis base (LB)→Lewis acid (LA) adduct connected via a C-C single bond [ 39 , 40 ] attracted our attention for possible applications of this small molecule adduct forming reaction in the synthesis of novel macromolecular electronic materials containing C 60 or both P3HT and C 60 , due to its fast reaction rate, quantitative product (adduct) formation, and simplicity of the approach.…”

Influence of solvent used on oxidative polymerization of Poly(3-hexylthiophene) in their chemical properties

“…The insertion of alkylic chain on position 3 of thiophene ring brings to this polymer the possibility of being melted and solubilized [2] . These polymers can be applied in fabrication of electroluminescent devices, as light emission diode (LED), Field Effect Transistors (FET) [1] , Polymer solar cells [3] .…”

Nanostructured star‐shaped polythiophene with tannic acid core: Synthesis, characterization, and its physicochemical properties

“…It should be pointed out that the polythiophene and its derivatives have attracted remarkable attention in scientific and industrial committees, in part due to combination of their chemical and physical properties. Extensive research efforts have been focused for the exploitations from polythiophenes in various applications such as (bio)chemical sensors, organic photovoltaics (OPVs), organic field‐effect transistors (OFETs), rechargeable batteries, organic light emitting diodes (OLEDs), electrical memory performance, biomedical fields, and many more.…”