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  1. Article ; Online: Development of the Squaramide Scaffold for High Potential and Multielectron Catholytes for Use in Redox Flow Batteries.

    Tracy, Jacob S / Broderick, Conor H / Toste, F Dean

    Journal of the American Chemical Society

    2024  Volume 146, Issue 17, Page(s) 11740–11755

    Abstract: Nonaqueous organic redox flow batteries (N-ORFBs) are a promising technology for grid-scale storage of energy generated from intermittent renewable sources. Their primary benefit over traditional aqueous RFBs is the wide electrochemical stability window ... ...

    Abstract Nonaqueous organic redox flow batteries (N-ORFBs) are a promising technology for grid-scale storage of energy generated from intermittent renewable sources. Their primary benefit over traditional aqueous RFBs is the wide electrochemical stability window of organic solvents, but the design of catholyte materials, which can exploit the upper range of this window, has proven challenging. We report herein a new class of N-ORFB catholytes in the form of squaric acid quinoxaline (SQX) and squaric acid amide (SQA) materials. Mechanistic investigation of decomposition in battery-relevant conditions via NMR, HRMS, and electrochemical methods enabled a rational design approach to optimizing these scaffolds. Three lead compounds were developed: a highly stable one-electron SQX material with an oxidation potential of 0.51 V vs Fc/Fc
    Language English
    Publishing date 2024-04-17
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.3c14776
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Utopia Point Bayesian Optimization Finds Condition-Dependent Selectivity for

    Dalton, Derek M / Walroth, Richard C / Rouget-Virbel, Caroline / Mack, Kyle A / Toste, F Dean

    Journal of the American Chemical Society

    2024  

    Abstract: Utopia Point Bayesian Optimization (UPBO) was used to identify reaction conditions that are highly selective for the formation of N1 and N2-methyl-3-aryl pyrazole constitutional isomers. UPBO was used to explore a wide chemical space and identify basic ... ...

    Abstract Utopia Point Bayesian Optimization (UPBO) was used to identify reaction conditions that are highly selective for the formation of N1 and N2-methyl-3-aryl pyrazole constitutional isomers. UPBO was used to explore a wide chemical space and identify basic reaction conditions for a typically acid-catalyzed Knorr pyrazole condensation. These studies revealed that selectivity in the reaction stems from a condition-dependent equilibrium of intermediates prior to dehydration. For the N2-methyl isomer reaction pathway, a hemiaminal intermediate was found to form reversibly under the reaction conditions, enabling a highly selective synthesis of the N2 isomer upon dehydrative workup. UPBO was able to successfully optimize conversion and selectivity simultaneously with search spaces of >1 million potential variable combinations without the need for high-performance computational resources.
    Language English
    Publishing date 2024-05-28
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.4c01616
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Correction to "Enantioselective Synthesis of Highly Substituted Furans by a Copper(II)-Catalyzed Cycloisomerization-Indole Addition Reaction".

    Rauniyar, Vivek / Wang, Z Jane / Burks, Heather E / Toste, F Dean

    Journal of the American Chemical Society

    2022  Volume 144, Issue 30, Page(s) 13981

    Language English
    Publishing date 2022-07-19
    Publishing country United States
    Document type Published Erratum
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.2c06800
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article: Development of high-voltage bipolar redox-active organic molecules through the electronic coupling of catholyte and anolyte structures.

    Tracy, Jacob S / Horst, Elena S / Roytman, Vladislav A / Toste, F Dean

    Chemical science

    2022  Volume 13, Issue 36, Page(s) 10806–10814

    Abstract: All-organic non-aqueous redox flow batteries (O-NRFBs) are a promising technology for grid-scale energy storage. However, most examples of high-voltage (>2 V) O-NRFBs rely upon the use of distinct anolytes and catholytes separated by a membrane or porous ...

    Abstract All-organic non-aqueous redox flow batteries (O-NRFBs) are a promising technology for grid-scale energy storage. However, most examples of high-voltage (>2 V) O-NRFBs rely upon the use of distinct anolytes and catholytes separated by a membrane or porous separator which can result in crossover of redox active material from one side of the battery to the other. The resulting electrolyte mixing leads to irreversible reductions in energy density and capacity. A potentially attractive solution to overcome this crossover issue is the implementation of symmetric flow batteries where a single bipolar molecule functions as both an anolyte and a catholyte. Herein, we report the development of a new class of bipolar redox active materials for use in such symmetric flow batteries through the electronic coupling of phenothiazine catholytes and phthalimide anolytes. Such a strategy results in hybrid molecules possessing higher cell voltages than what could be obtained together by their uncoupled building blocks. Performance in flow batteries is demonstrated for two members of this new class of molecules, with the highest performing candidate featuring a Δ
    Language English
    Publishing date 2022-09-01
    Publishing country England
    Document type Journal Article
    ZDB-ID 2559110-1
    ISSN 2041-6539 ; 2041-6520
    ISSN (online) 2041-6539
    ISSN 2041-6520
    DOI 10.1039/d2sc03450f
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Mechanism of Photoredox-Initiated C-C and C-N Bond Formation by Arylation of IPrAu(I)-CF

    Kim, Suhong / Toste, F Dean

    Journal of the American Chemical Society

    2019  Volume 141, Issue 10, Page(s) 4308–4315

    Abstract: Herein, we report on the photoredox-initiated gold-mediated C( ... ...

    Abstract Herein, we report on the photoredox-initiated gold-mediated C(sp
    MeSH term(s) Alkylation/radiation effects ; Azo Compounds/chemistry ; Benzene Derivatives/chemical synthesis ; Catalysis/radiation effects ; Coordination Complexes/chemistry ; Coordination Complexes/radiation effects ; Gold/chemistry ; Gold/radiation effects ; Light ; Oxidation-Reduction/radiation effects ; Succinimides/chemical synthesis
    Chemical Substances Azo Compounds ; Benzene Derivatives ; Coordination Complexes ; Succinimides ; Gold (7440-57-5)
    Language English
    Publishing date 2019-01-17
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.8b11273
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: Tunable Electrochemical Entropy through Solvent Ordering by a Supramolecular Host.

    Xia, Kay T / Rajan, Aravindh / Surendranath, Yogesh / Bergman, Robert G / Raymond, Kenneth N / Toste, F Dean

    Journal of the American Chemical Society

    2023  Volume 145, Issue 46, Page(s) 25463–25470

    Abstract: An aqueous electrochemically controlled host-guest encapsulation system demonstrates a large and synthetically tunable redox entropy change. Electrochemical entropy is the basis for thermally regenerative electrochemical cycles (TRECs), which utilize ... ...

    Abstract An aqueous electrochemically controlled host-guest encapsulation system demonstrates a large and synthetically tunable redox entropy change. Electrochemical entropy is the basis for thermally regenerative electrochemical cycles (TRECs), which utilize reversible electrochemical processes with large molar entropy changes for thermogalvanic waste-heat harvesting and electrochemical cooling, among other potential applications. A supramolecular host-guest system demonstrates a molar entropy change of 4 times that of the state-of-the-art aqueous TREC electrolyte potassium ferricyanide. Upon encapsulation of a guest, water molecules that structurally resemble amorphous ice are displaced from the host cavity, leveraging a change in the degrees of freedom and ordering of the solvent rather than the solvation of the redox-active species to increase entropy. The synthetic tunability of the host allows rational optimization of the system's Δ
    Language English
    Publishing date 2023-11-13
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.3c10145
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Hybrid Catalysts for Enantioselective Photo-Phosphoric Acid Catalysis.

    Rolka, Alessa B / Archipowa, Nataliya / Kutta, Roger J / König, Burkhard / Toste, F Dean

    The Journal of organic chemistry

    2023  Volume 88, Issue 10, Page(s) 6509–6522

    Abstract: The syntheses of two novel, organic, and chiral photocatalysts are presented. By combining donor-acceptor cyanoarene-based photocatalysts with a chiral phosphoric acid, bifunctional catalysts have been designed. In preliminary proof-of-concept reactions, ...

    Abstract The syntheses of two novel, organic, and chiral photocatalysts are presented. By combining donor-acceptor cyanoarene-based photocatalysts with a chiral phosphoric acid, bifunctional catalysts have been designed. In preliminary proof-of-concept reactions, their use in both enantioselective energy transfer and photoredox catalysis is demonstrated.
    Language English
    Publishing date 2023-04-26
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.3c00191
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    In stock of ZB MED Cologne/Königswinter

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  8. Article: Mechanism of Photoredox-Initiated C–C and C–N Bond Formation by Arylation of IPrAu(I)–CF3 and IPrAu(I)–Succinimide

    Kim, Suhong / Toste, F. Dean

    Journal of the American Chemical Society. 2019 Jan. 17, v. 141, no. 10

    2019  

    Abstract: Herein, we report on the photoredox-initiated gold-mediated C(sp2)–CF3 and C(sp2)–N coupling reactions. By adopting gold as a platform for probing metallaphotoredox catalysis, we demonstrate that cationic gold(III) complexes are the key intermediates of ... ...

    Abstract Herein, we report on the photoredox-initiated gold-mediated C(sp2)–CF3 and C(sp2)–N coupling reactions. By adopting gold as a platform for probing metallaphotoredox catalysis, we demonstrate that cationic gold(III) complexes are the key intermediates of the C–C and C–N coupling reactions. The high-valent gold(III) intermediates are accessed by virtue of photoredox catalysis through a radical chain process. In addition, the bond-forming step of the coupling reactions is the reductive elimination from cationic gold(III) intermediates, which is supported by isolation and crystallographic characterization of key Au(III) intermediates.
    Keywords arylation ; catalytic activity ; chemical bonding ; gold ; redox reactions
    Language English
    Dates of publication 2019-0117
    Size p. 4308-4315.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.8b11273
    Database NAL-Catalogue (AGRICOLA)

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  9. Article ; Online: Homogeneous Gold Redox Chemistry: Organometallics, Catalysis, and Beyond.

    Huang, Banruo / Hu, Mingyou / Toste, F Dean

    Trends in chemistry

    2020  Volume 2, Issue 8, Page(s) 707–720

    Abstract: Gold redox chemistry holds the promise of unique reactivities and selectivities that are different to other transition metals. Recent studies have utilized strain release, ligand design, and photochemistry to promote the otherwise sluggish oxidative ... ...

    Abstract Gold redox chemistry holds the promise of unique reactivities and selectivities that are different to other transition metals. Recent studies have utilized strain release, ligand design, and photochemistry to promote the otherwise sluggish oxidative addition to Au(I) complexes. More details on the reductive elimination from Au(III) complexes have also been revealed. These discoveries have facilitated the development of gold redox catalysis and will continue to offer mechanistic insight and inspiration for other transition metals. This review highlights how research in organometallic chemistry has led to gold redox catalysis, as well as applications in materials science, bioconjugation, and radiochemical synthesis.
    Language English
    Publishing date 2020-06-02
    Publishing country United States
    Document type Journal Article
    ISSN 2589-5974
    ISSN (online) 2589-5974
    DOI 10.1016/j.trechm.2020.04.012
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article: Gold catalysis for organic synthesis II.

    Toste, F Dean

    Beilstein journal of organic chemistry

    2013  Volume 9, Page(s) 2040–2041

    Language English
    Publishing date 2013-10-09
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2192461-2
    ISSN 1860-5397
    ISSN 1860-5397
    DOI 10.3762/bjoc.9.241
    Database MEDical Literature Analysis and Retrieval System OnLINE

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