Evidence map›Paper›PMID 30897327›Full record

ArticleJournal of the American Chemical Society2019

Discovery and Elucidation of Counteranion Dependence in Photoredox Catalysis.

Elliot P Farney, Steven J Chapman, Wesley B Swords, Marco D Torelli, Robert J Hamers, Tehshik P Yoon

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.

0numbers the graph read from it
0cells of the map it votes in
34citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

34 citing papers in PubMed.

  1. Article
  2. A Bis(arenesulfonyl) Peroxide, an Ambient-Stable Oxidant, Is a Strong p‑Dopant for Organic Semiconductors.Chemistry of materials : a publication of the American Chemical Society · 2026
    Article
  3. Enantioselective Contrathermodynamic Olefin Isomerization.Journal of the American Chemical Society · 2026
    Article
  4. Article
  5. Article
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  15. Article
  16. AgNature communications · 2024
    Article
  17. Chemical science · 2023
    Article
  18. Article
  19. Article
  20. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

6 authors.

Elliot P FarneyDepartment of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , United States.
Steven J ChapmanDepartment of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , United States.ORCID 0000-0003-1570-4580
Wesley B SwordsDepartment of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , United States.ORCID 0000-0002-2986-326X
Marco D TorelliDepartment of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , United States.ORCID 0000-0002-7691-6491
Robert J HamersDepartment of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , United States.ORCID 0000-0003-3821-9625
Tehshik P YoonDepartment of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , United States.ORCID 0000-0002-3934-4973

Funding

Visible Light PhotocatalysisR01GM095666 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI YOON, TEHSHIK P · 2011 to 2022
$4.2M
QExactive (Orbitrap) mass spectrometerS10OD020022 · OD · UNIVERSITY OF WISCONSIN-MADISON · PI VESTLING, MARTHA M · 2015 to 2015
$483k
NIGMS NIH HHS R01 GM095666NIH HHS S10 OD020022
6 · The paper itself

Abstract

Over the past decade, there has been a renewed interest in the use of transition metal polypyridyl complexes as photoredox catalysts for a variety of innovative synthetic applications. Many derivatives of these complexes are known, and the effect of ligand modifications on their efficacy as photoredox catalysts has been the subject of extensive, systematic investigation. However, the influence of the photocatalyst counteranion has received little attention, despite the fact that these complexes are generally cationic in nature. Herein, we demonstrate that counteranion effects exert a surprising, dramatic impact on the rate of a representative photocatalytic radical cation Diels-Alder reaction. A detailed analysis reveals that counteranion identity impacts multiple aspects of the reaction mechanism. Most notably, photocatalysts with more noncoordinating counteranions yield a more powerful triplet excited state oxidant and longer radical cation chain length. It is proposed that this counteranion effect arises from Coulombic ion-pairing interactions between the counteranion and both the cationic photoredox catalyst and the radical cation intermediate, respectively. The comparatively slower rate of reaction with coordinating counteranions can be rescued by using hydrogen-bonding anion binders that attenuate deleterious ion-pairing interactions. These results demonstrate the importance of counteranion identity as a variable in the design and optimization of photoredox transformations and suggest a novel strategy for the optimization of organic reactions using this class of transition metal photocatalysts.

Indexed as

CatalysisCoordination ComplexesCyclizationLightMolecular ConformationOxidation-ReductionPhotochemical ProcessesRutheniumCoordination ComplexesRuthenium

Identifiers

PMID30897327
PMCPMC6519111

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Registered trials

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.