Silia<i>Cat</i>: A Versatile Catalyst Series for Synthetic Organic Chemistry

Ciriminna, Rosaria; Pandarus, Valerica; Fidalgo, Alexandra; Ilharco, Laura M.; Béland, François; Pagliaro, Mario

doi:10.1021/acs.oprd.5b00137

Cited by 44 publications

(18 citation statements)

References 64 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 catalyst consists of an organosilica matrix functionalized with diphenylphosphine (DPP) ligands bound to Pd II . SiliaCat DPP‐Pd has been used for a wide range of Pd‐catalyzed organic transformations and, importantly, has shown a high resistance against catalyst leaching in reactions involving both heterogeneous Pd 0 and homogeneous Pd II species in the reaction mechanism …”

Section: Resultsmentioning

confidence: 99%

Design and Development of Pd‐Catalyzed Aerobic N‐Demethylation Strategies for the Synthesis of Noroxymorphone in Continuous Flow Mode

Gutmann

Cantillo

Weigl³

et al. 2017

Eur J Org Chem

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Strategies for the generation of noroxymorphone from 14‐hydroxymorphinone are presented. Noroxymorphone is the key intermediate in the synthesis of various opioid antagonists, including naloxone, naltrexone, and nalmefene, as well as mixed agonists‐antagonists such as nalbuphine. The transformation requires removal of the N‐methyl group from the naturally occurring opiates and double‐bond hydrogenation. The pivotal reaction step thereby is an N‐methyl oxidation with colloidal palladium(0) as catalyst and pure oxygen as terminal oxidant. The reaction produces a 1,3‐oxazolidine intermediate, which can be readily hydrolyzed to the corresponding secondary amine. Different reaction sequences and the use of various phenol protecting groups were explored. The most direct route consumes only H2, O2, and H2O as stoichiometric reagents and produces only H2O as a byproduct. Challenges inherent to gas/liquid reactions with oxygen as oxidant have been addressed by developing a continuous flow process.

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“…Demonstrating the industrial potential of the technology, noble metal (Pd, Pt) nanoparticles sol‐gel entrapped in ORMOSIL matrices are widely employed as selective catalysts for multiple synthetic organic chemistry key conversions …”

Section: Outlook and Conclusionmentioning

confidence: 99%

AurOrGlass: ORMOSIL Sol‐Gel Glasses Functionalized with Gold Nanoparticles for Advanced Optical Applications

Ciriminna

Fidalgo²,

Ilharco³

et al. 2019

ChemistrySelect

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SiliaCat: A Versatile Catalyst Series for Synthetic Organic Chemistry

Cited by 44 publications

References 64 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

Design and Development of Pd‐Catalyzed Aerobic N‐Demethylation Strategies for the Synthesis of Noroxymorphone in Continuous Flow Mode

AurOrGlass: ORMOSIL Sol‐Gel Glasses Functionalized with Gold Nanoparticles for Advanced Optical Applications

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