2018
DOI: 10.1002/anie.201711692
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Generating Hydrated Electrons for Chemical Syntheses by Using a Green Light‐Emitting Diode (LED)

Abstract: We present the first working system for accessing and utilizing laboratory-scale concentrations of hydrated electrons by photoredox catalysis with a green light-emitting diode (LED). Decisive are micellar compartmentalization and photon pooling in an intermediate that decays with second-order kinetics. The only consumable is the nontoxic and bioavailable vitamin C. A turnover number of 1380 shows the LED method to be on par with electron generation by high-power pulsed lasers, but at a fraction of the cost. Th… Show more

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Cited by 62 publications
(100 citation statements)
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References 31 publications
(100 reference statements)
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“…The eaq- decay (for a representative trace, see the inset of Figure b) is monoexponential, and a catalyst‐independent lifetime of 194 ns rules out an influence of the ruthenium complexes on the further fate of eaq- after its generation. This is consistent with our earlier investigations, which pinpointed the capture of eaq- by residual ascorbate monoanion HAsc − as the lifetime‐limiting factor in the absence of deliberately added scavengers. The p K a of HAsc − is 11.74; hence, the HAsc − concentration is about 7.5 m m in the experiments of this work.…”
Section: Resultssupporting
confidence: 93%
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“…The eaq- decay (for a representative trace, see the inset of Figure b) is monoexponential, and a catalyst‐independent lifetime of 194 ns rules out an influence of the ruthenium complexes on the further fate of eaq- after its generation. This is consistent with our earlier investigations, which pinpointed the capture of eaq- by residual ascorbate monoanion HAsc − as the lifetime‐limiting factor in the absence of deliberately added scavengers. The p K a of HAsc − is 11.74; hence, the HAsc − concentration is about 7.5 m m in the experiments of this work.…”
Section: Resultssupporting
confidence: 93%
“…In a recent communication, we have presented the first photoredox catalytic system that generates eaq- on a laboratory scale while being both user‐friendly and sustainable through operating with a green light‐emitting diode (LED) instead of a high‐power laser and consuming only a bioavailable sacrificial species. After an attempt at replacing the latter to accommodate a specific class of synthetic applications, here we focus on improving the catalyst.…”
Section: Introductionmentioning
confidence: 99%
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“…[7,16] In contrast, the much lower accessibilityo fP AscH À to the species in the aqueous bulk virtually removes this coupling (SI-3.2 and 4.2.2). [7,16] In contrast, the much lower accessibilityo fP AscH À to the species in the aqueous bulk virtually removes this coupling (SI-3.2 and 4.2.2).…”
Section: Resultsmentioning
confidence: 99%
“…While the repetitive decay traces of e À aq in Figure 2a highlight this difference, they primarily demonstratet he successful operation of either system as ar egenerative electron source. [2,7,10,16,21] An attack of e À aq triggerst he quasi-instantaneous dissociation of ClAc into ac hloride ion and ac arboxymethyl radical. At the intensity used, each flash ionizedm ore than 50 %o fA ntNH 2 (see also SI-2.2);a nd over the total series of 21 sub-experiments, the accumulated e À aq concentration amounted to more than 10 times the catalyst concentration.…”
Section: Resultsmentioning
confidence: 99%