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Isolable zwitterionic pyridinio-semiquinone ?-radicals: mild and efficient single-step access to stable radicals

Isolable zwitterionic pyridinio-semiquinone ?-radicals: mild and efficient single-step access to stable radicals
Isolable zwitterionic pyridinio-semiquinone ?-radicals: mild and efficient single-step access to stable radicals
A rational design based on the proton-coupled electron transfer (PCET) concept allows us to structurally characterize for the first time isolable, air- and moisture-stable semiquinone radicals in a zwitterionic neutral form. The presence of an alkoxy and the bulky pyridinio substituents causes only a minor perturbation of either the redox potentials or the spectral UV-vis characteristics of the semiquinone core but significantly stabilizes the new radicals.
1523-7060
2261-2264
Yi, Chenyi
fc1c6645-bfa9-44a7-8a91-8d9e74d5df2b
Blum, Carmen
99f93361-478a-4997-b5e0-61682ef8dc25
Liu, Shi-Xia
546635e3-8931-436e-8456-298ac2a3134d
Keene, Tony D.
fb859c26-6a1d-4c43-a15f-f329bc8d34d7
Frei, Gabriela
7875bb74-d076-4b40-b63b-828e28fd380e
Neels, Antonia
a8d7f75b-c2c2-4d1f-bfb4-d538fd4c9073
Decurtins, Silvio
331985a5-2121-47e4-a4b2-2fd09f8cabfd
Yi, Chenyi
fc1c6645-bfa9-44a7-8a91-8d9e74d5df2b
Blum, Carmen
99f93361-478a-4997-b5e0-61682ef8dc25
Liu, Shi-Xia
546635e3-8931-436e-8456-298ac2a3134d
Keene, Tony D.
fb859c26-6a1d-4c43-a15f-f329bc8d34d7
Frei, Gabriela
7875bb74-d076-4b40-b63b-828e28fd380e
Neels, Antonia
a8d7f75b-c2c2-4d1f-bfb4-d538fd4c9073
Decurtins, Silvio
331985a5-2121-47e4-a4b2-2fd09f8cabfd

Yi, Chenyi, Blum, Carmen, Liu, Shi-Xia, Keene, Tony D., Frei, Gabriela, Neels, Antonia and Decurtins, Silvio (2009) Isolable zwitterionic pyridinio-semiquinone ?-radicals: mild and efficient single-step access to stable radicals. Organic Letters, 11 (11), 2261-2264. (doi:10.1021/ol900559p).

Record type: Article

Abstract

A rational design based on the proton-coupled electron transfer (PCET) concept allows us to structurally characterize for the first time isolable, air- and moisture-stable semiquinone radicals in a zwitterionic neutral form. The presence of an alkoxy and the bulky pyridinio substituents causes only a minor perturbation of either the redox potentials or the spectral UV-vis characteristics of the semiquinone core but significantly stabilizes the new radicals.

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More information

Published date: 29 April 2009
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry, Faculty of Natural and Environmental Sciences

Identifiers

Local EPrints ID: 351388
URI: http://eprints.soton.ac.uk/id/eprint/351388
ISSN: 1523-7060
PURE UUID: c877fa5e-8cef-4b14-ad6b-deca7899f05c
ORCID for Tony D. Keene: ORCID iD orcid.org/0000-0003-2297-4327

Catalogue record

Date deposited: 22 Apr 2013 10:25
Last modified: 06 Oct 2020 23:25

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