2020
DOI: 10.1021/jacs.0c05507
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Helical Carbenium Ion: A Versatile Organic Photoredox Catalyst for Red-Light-Mediated Reactions

Abstract: Red light has the advantages of low energy, less health risk and high penetration depth through various media. Herein, a helical carbenium ion (N,N'-din -propyl-1,13-dimethoxyquinacridinium (nPr-DMQA+) tetrafluoroborate) has been used as an organic photoredox catalyst for photoreductions and photooxidations in the presence of red ligh (max = 640 nm). It has catalyzed red-lightmediated dual transition-metal/photoredox-catalyzed C-H arylation and intermolecular atom transfer radical addition through oxidative qu… Show more

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Cited by 109 publications
(89 citation statements)
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“…The DMQA radicals are catalytic intermediates in the lightinduced transformations catalysed by DMQA + . 41 The structure/ properties relationship of these radicals presented in this work will help develop more durable and efficient photocatalysts. Furthermore, due to their high persistence, widerange optical absorption, reversible redox properties, and spin localization with minimal steric protection, these helical radicals have great potential for photocatalysis, optical, and materials applications.…”
Section: Discussionmentioning
confidence: 92%
See 1 more Smart Citation
“…The DMQA radicals are catalytic intermediates in the lightinduced transformations catalysed by DMQA + . 41 The structure/ properties relationship of these radicals presented in this work will help develop more durable and efficient photocatalysts. Furthermore, due to their high persistence, widerange optical absorption, reversible redox properties, and spin localization with minimal steric protection, these helical radicals have great potential for photocatalysis, optical, and materials applications.…”
Section: Discussionmentioning
confidence: 92%
“…We recently reported the use of [4]helical carbenium ions, DMQA + , as efficient photocatalysts to generate [4]helicene radicals in situ, using a red LED as the energy source. 41 The quinacridyl scaffold, rst introduced by Laursen, 42 contains bridging amine groups that allow facile structural modication, and its heterocyclic core can be easily functionalized. 43 The isolation and characterization of a series of [4]helicene radicals would provide a valuable insight for the design of new [4]helical carbenium-ion photocatalysts.…”
Section: Introductionmentioning
confidence: 99%
“…Most commonly used photocatalysts absorb in the blue region of the visible spectrum, although new catalysts are being developed which can absorb longer wavelength red light. 20 Redox potentials, excited state lifetimes, and absorption maxima for commonly used photocatalysts are readily available. 17,18 Practically, photocatalysis is simple to perform.…”
Section: Photoredox Catalysismentioning
confidence: 99%
“…Before starting a test on the photocatalytic reactivity of 4, we calculated its excited-state energy (E 0,0 ) and its excited-state reduction [E 1/2 (C +* /C • )] and oxidation potentials [E 1/2 (C •++ /C +* )], based on previously reported data 18b, 19 and our own experimental measurements. 23 The excitation energy (E 0,0 ) was estimated by calculating the energy of the wavelength intersection between normalized absorption and emission spectra of 4. 3a The excited-state reduction potential E 1/2 (C +* /C • ) was estimated from the expression E 1/2 (C +* /C • ) = E 1/2 (C + /C • ) + E 0,0 , and the excited-state oxidation potential E 1/2 (C •++ /C +* ) was estimated from the expression E 1/2 (C •++ /C +* ) = E 1/2 (C •++ /C + ) -E 0,0 .…”
Section: Scheme 3 the Only Example Of Photocatalysis By Dmqa + Previomentioning
confidence: 99%