Facile synthesis of unsymmetrical and π-extended furan-diketopyrrolopyrrole derivatives through C–H direct (hetero)arylation using a heterogeneous catalyst system

Areephong, Jetsuda; Hendsbee, Arthur D.; Welch, Gregory C.

doi:10.1039/c5nj01150g

Cited by 26 publications

(13 citation statements)

References 31 publications

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“…In our previous work, we have highlighted the ease and straightforward synthetic access to PDI precursor building blocks, and PDI‐DPP‐PDI , a feature not commonly shared among high performance non‐fullerene acceptors. This was accomplished by applying a direct (hetero)arylation cross‐coupling protocol and a re‐usable silica‐supported palladium catalyst, Silia Cat ® DPP‐Pd, a method that has been successfully employed in the synthesis of a wide range of molecular materials . Following this approach, PDI‐DPP‐PDI was accessed in yields up to 70% and amounts up to 0.5 g. Considering the impressive performance and stability metrics for this non‐fullerene acceptor and the desire for scalable materials for eventual large‐scale device fabrication, we carried out a multigram synthesis of PDI‐DPP‐PDI to highlight the potential for widespread use of this material moving forward…”

Section: Multigram Synthesismentioning

confidence: 99%

Toward a Universally Compatible Non‐Fullerene Acceptor: Multi‐Gram Synthesis, Solvent Vapor Annealing Optimization, and BDT‐Based Polymer Screening

et al. 2018

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To highlight the benefits of the organic dye PDI-DPP-PDI for use in fullerenefree organic solar cells, herein is demonstrated how this material can meet scalability demands through a multigram scale direct heteroarylation coupling reaction, and performance demands through a post-deposition solvent vapor annealing treatment. A solvent vapor annealing method has been utilized to screen a comprehensive selection of ethereal, aromatic, and chlorinated solvents. Upon transitioning to these eight alternative solvents, significant performance increase over the chloroform standard is noted for all solvents, with tetrahydrofuran and o-dichlorobenzene leading to the highest performance devices post-treatment. This trend, including an open-circuit voltage greater than 1 V proved to be consistent with four different BDT-based donor polymers, PTB7-Th, PBDB-T, J61, and TTFQx-T1. The highest performing devices are achieved with PTB7-Th and TTFQx-T1, with PCEs reaching 6.2 and 5.7%, respectively, when tetrahydrofuran solvent vapor annealing is combined with interfacial modification of the ZnO electron-transport layer.

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Section: Multigram Synthesismentioning

confidence: 99%

Toward a Universally Compatible Non‐Fullerene Acceptor: Multi‐Gram Synthesis, Solvent Vapor Annealing Optimization, and BDT‐Based Polymer Screening

et al. 2018

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“…The use of this heterogeneous catalyst for C-H bond activation has proven to be a versatile synthetic strategy that has been extensively used within our research group. 51,[61][62][63] SiliaCat® DPP-Pd has been shown to not only match homogeneous alternatives, but also circumvent inert reaction conditions, and diminish trace Pd metal impurities in the nal product. 61 The use of the heterogeneous catalyst also simplied the reaction work up and purication since it can be easily removed from the soluble product simply through vacuum ltration.…”

Section: Materials Synthesismentioning

confidence: 99%

The structural evolution of an isoindigo-based non-fullerene acceptor for use in organic photovoltaics

et al. 2015

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The structural evolution of a functional isoindigo-based non-fullerene acceptor led to the development of three new materials to address the deficiencies of the original framework. Owing to the versatility of the structure and the flexibility of the synthetic procedures, these three new materials were accessible from previously optimized reaction conditions and similar precursor materials. The influence of structural modification on the optical, electrochemical and thermal properties were assessed and correlated with DFT calculations to provide compelling evidence for the effect of each substitution and how they relate to each particular adaptation. The structure-property relationships were investigated for their photovoltaic performance in solution processable BHJ devices fabricated in inverted architectures. Evaluation of device performance demonstrated that a single modification did not improve on the efficiency of the original structure, but the combination of both induced nonplanarity, and increased electron affinity of the fourth iteration showed the potential of our framework, with PCE reaching 1.9%.

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“…To achieve this goal, three different catalytic systems, involved in the functionalization of DPP derivatives via DHA, were used and evaluated herein [ 25 , 26 , 27 , 28 ]. However, for comparative purposes, all polymerizations were all carried out in dimetylacetamide at 80 °C in presence of potassium carbonate and pivalic acid.…”

Section: Resultsmentioning

confidence: 99%

Direct (Hetero)Arylation Polymerization of a Spirobifluorene and a Dithienyl-Diketopyrrolopyrrole Derivative: New Donor Polymers for Organic Solar Cells

et al. 2018

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The synthesis and preliminary evaluation as donor material for organic photovoltaics of the poly(diketopyrrolopyrrole-spirobifluorene) (PDPPSBF) is reported herein. Prepared via homogeneous and heterogeneous direct (hetero)arylation polymerization (DHAP), through the use of different catalytic systems, conjugated polymers with comparable molecular weights were obtained. The polymers exhibited strong optical absorption out to 700 nm as thin-films and had appropriate electronic energy levels for use as a donor with PC70BM. Bulk heterojunction solar cells were fabricated giving power conversion efficiencies above 4%. These results reveal the potential of such polymers prepared in only three steps from affordable and commercially available starting materials.

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Facile synthesis of unsymmetrical and π-extended furan-diketopyrrolopyrrole derivatives through C–H direct (hetero)arylation using a heterogeneous catalyst system

Cited by 26 publications

References 31 publications

Toward a Universally Compatible Non‐Fullerene Acceptor: Multi‐Gram Synthesis, Solvent Vapor Annealing Optimization, and BDT‐Based Polymer Screening

Toward a Universally Compatible Non‐Fullerene Acceptor: Multi‐Gram Synthesis, Solvent Vapor Annealing Optimization, and BDT‐Based Polymer Screening

The structural evolution of an isoindigo-based non-fullerene acceptor for use in organic photovoltaics

Direct (Hetero)Arylation Polymerization of a Spirobifluorene and a Dithienyl-Diketopyrrolopyrrole Derivative: New Donor Polymers for Organic Solar Cells

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