Detail publikace

Hole-mediated photoredox catalysis: tris(p-substituted)biarylaminium radical cations as tunable, precomplexing and potent photooxidants

Wu, SZ. Zurauskas, J. Domanski, M. Hitzfeld, PS. Butera, V. Scott, DJ. Rehbein, J. Kumar, A. Thyrhaug, E. Hauer, J. Barham, JP.

Originální název

Hole-mediated photoredox catalysis: tris(p-substituted)biarylaminium radical cations as tunable, precomplexing and potent photooxidants

Typ

článek v časopise ve Web of Science, Jimp

Jazyk

angličtina

Originální abstrakt

As a combination of visible light photoredox catalysis and synthetic organic electrochemistry, electrochemically-mediated photoredox catalysis emerged as a powerful synthetic technique in recent years, overcoming fundamental limitations of electrochemistry and photoredox catalysis in the single electron transfer activation of small organic molecules. Herein we report a tunable class of electroactivated photoredox catalyst, tri(para-substituted)biarylamines, that become superoxidants in their photoexcited states even able to oxidize molecules beyond the solvent window limits of cyclic voltammetry (such as polyfluorobenzene and trifluorotoluene). Furthermore, we demonstrate that precomplexation not only permits the excited state photochemistry of tris(para-substituted)biarylaminium cations to overcome picosecond lifetime, but enables and rationalizes the surprising photochemistry of their higher-order doublet (D-n) excited states, unlocking extremely high oxidative potentials (up to a record-breaking similar to+4.4 V vs. SCE).

Klíčová slova

C-H AMINATION; ORGANIC ELECTROSYNTHESIS; LIGHT; DYNAMICS; ELECTROCHEMISTRY; REDUCTION; OXIDATION; STATES

Autoři

Wu, SZ.; Zurauskas, J.; Domanski, M.; Hitzfeld, PS.; Butera, V.; Scott, DJ.; Rehbein, J.; Kumar, A.; Thyrhaug, E.; Hauer, J.; Barham, JP.

Vydáno

21. 3. 2021

Nakladatel

ROYAL SOC CHEMISTRY

Místo

CAMBRIDGE

ISSN

2052-4129

Periodikum

Organic Chemistry Frontiers

Ročník

8

Číslo

6

Stát

Čínská lidová republika

Strany od

1

Strany do

12

Strany počet

12

URL

https://pubs.rsc.org/en/content/articlelanding/2021/QO/D0QO01609H#!divAbstract

BibTex

@article{BUT171854,
  author="Wu, SZ. and Zurauskas, J. and Domanski, M. and Hitzfeld, PS. and Butera, V. and Scott, DJ. and Rehbein, J. and Kumar, A. and Thyrhaug, E. and Hauer, J. and Barham, JP.",
  title="Hole-mediated photoredox catalysis: tris(p-substituted)biarylaminium radical cations as tunable, precomplexing and potent photooxidants",
  journal="Organic Chemistry Frontiers",
  year="2021",
  volume="8",
  number="6",
  pages="1--12",
  doi="10.1039/d0qo01609h",
  issn="2052-4129",
  url="https://pubs.rsc.org/en/content/articlelanding/2021/QO/D0QO01609H#!divAbstract"
}