1231160-82-9Relevant articles and documents
Synthetic control of structural order in N-alkylthieno[3,4- c ]pyrrole-4,6-dione-based polymers for efficient solar cells
Piliego, Claudia,Holcombe, Thomas W.,Douglas, Jessica D.,Woo, Claire H.,Beaujuge, Pierre M.,Frechet, Jean M. J.
, p. 7595 - 7597 (2010)
The correlation between the nature of alkyl substituents on N-alkylthieno[3,4-c]pyrrole-4,6-dione (TPD)-based polymers and solar cell device performance has been investigated. After adjusting device parameters, these TPD-based polymers used with PC61BM provided photovoltaic responses ranging from 4.0% to 6.8%, depending on the size and shape of the alkyl solubilizing groups. Further, we have correlated the effect of the alkyl groups on the structural order and orientation of the polymer backbone using grazing incidence X-ray scattering analysis, and we have demonstrated how fine-tuning of these parameters can improve the power conversion efficiency.
Copper-catalyzed direct C-H arylation of thieno[3,4-c]pyrrole-4,6-dione (TPD): Toward efficient and low-cost synthesis of ??-functional small molecules
Song, Yi-Ting,Lin, Po-Han,Liu, Ching-Yuan
, p. 3761 - 3768 (2014)
A series of thieno[3,4-c]pyrrole-4,6-dione (TPD)-based functional small molecules were efficiently synthesized through direct C-H arylations using inexpensive copper salts. In this study, we examined all required reaction parameters including various copper complexes, ligands, bases, and (co)-solvents. Under the optimum reaction conditions, the C-H arylation proceeded smoothly and a variety of functional groups such as ester, nitrile, fluoride, chloride, triazene, and amine were tolerated. This method provides a step-economical and relatively low-cost synthetic alternative to presently used coupling reactions for the preparation of TPD-containing p-functional materials.
Synthesis of TPD–thiophene-based small molecule donor for organic photovoltaic cells
Lim, Eunhee
, p. 87 - 93 (2016)
The donor–acceptor–donor (D–A–D) type small molecule, TPD2T, was synthesized by the Stille coupling reaction and consisted of the electron-withdrawing thiene[3,4-c]pyrrole-4,6-dione (TPD) unit as an electron-accepting (A) core and electron-rich bithiophene units as electron-donating (D) groups. The absorption maximum of the TPD2T film was observed at 460?nm, and was broader and red-shifted compared to that in solution (λmax = 450?nm). Organic photovoltaic cells fabricated with the conventional and inverted structures both exhibited similar power conversion efficiencies of 0.14–0.15%. Despite the low short-circuit current values, the TPD2T devices showed high open-circuit voltages of over 1.0?V owing to the relatively low-lying HOMO level of TPD2T (?5.4?eV).
Synthesis and characterization of new thieno[3,4-c]pyrrole-4,6-dione derivatives for photovoltaic applications
Najari, Ahmed,Beaupre, Serge,Berrouard, Philippe,Zou, Yingping,Pouliot, Jean-Remi,Lepage-Perusse, Charlotte,Leclerc, Mario
, p. 718 - 728 (2011)
A new class of low-bandgap copolymers based on benzodithiophene (BDT) and thieno[3,4-c]pyrrole-4,6-dione (TPD) units is reported. Chemical modifications of the conjugated backbone promote both high molecular weights and processability while allowing for tuning of the electronic properties. Copolymers with substituted thiophene spacers (alkyl chains facing the BDT unit) or unsubstituted thiophene spacers tend to have low power conversion efficiencies (PCE less than 1%) due to a bad morphology of the active layer, whereas copolymers with substituted thiophene spacers (alkyl chains facing TPD unit) show enhanced morphology and PCEs up to of 3.9%. Finally, BDT-TPD copolymers without any thiophene spacers still show the best performances with power conversion efficiencies up to 5.2%. The synthesis and characterization of new electroactive and photoactive copolymers based on benzodithiophene (BDT) and thieno[3,4-c]pyrrole-4,6-dione (TPD) units are described. The copolymers are synthesized with or without thiophene spacers in order to tune the electronic properties and to control the morphology of the active layer in bulk heterojunction solar cells. The potential of these new materials in photovoltaic devices is investigated.
Structural Insight into Aggregation and Orientation of TPD-Based Conjugated Polymers for Efficient Charge-Transporting Properties
Lim, Dae-Hee,Kim, Yeon-Ju,Kim, Yeong-A,Hwang, Kyoungtae,Park, Jong-Jin,Kim, Dong-Yu
, p. 4629 - 4638 (2019/05/08)
In this study, we obtained a new structural insight into the charge-transporting properties in TPD-based polymers that cannot be solely explained in terms of the type of orientation. We synthesized two types of copolymers comprising mono-TPD or bis-TPD as the accepting unit. Although the planarity and energy levels are similar with the mono-TPD unit, the aggregation state is quite different, and the X-aggregation tendency seems to be stronger when the bis-TPD unit is incorporated. In the case of TPD1, an effective π-πorbital overlap is found to originate from the H-aggregates, and 3D charge transport pathways are formed with a bimodal orientation of edge-on and face-on, resulting in an efficient charge transportation (1.84 cm2·V-1·s-1 of hole and 0.31 cm2·V-1·s-1 of electron). In contrast, despite the well-aligned edge-on orientation of TPD2, it exhibited a relatively very low mobility and splitted emission characteristics in photoluminescence spectra because of the tilted intermolecular stacking pattern with an X-shape (0.015 cm2·V-1·s-1 for hole and 0.16 cm2·V-1·s-1 for electron). An overall characterization of the semiconducting polymers was performed, and it was found that the type of aggregation in the final thin films, such as H- or X-aggregation, is indeed important and perhaps more important than the orientation to obtain polymers with a high charge carrier mobility.
