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Formation of persistent organic diradicals from N,N′-diphenyl-3,7-diazacyclooctanes

Formation of persistent organic diradicals from N,N′-diphenyl-3,7-diazacyclooctanes
Formation of persistent organic diradicals from N,N′-diphenyl-3,7-diazacyclooctanes
N,N′-Diphenyl-3,7-diazacyclooctane and structurally related N,N′-diphenylbispidine derivatives react with silver(I) ions in a high-yielding C–C coupling reaction to produce dication–diradical species, with the silver ions serving a double function both as template and as an oxidant. The resulting bis(benzidino)phane derivatives are persistent organic radicals, stable for several months in solution as well as in the solid state, at room temperature and above, as well as being exposed to the atmosphere. The molecular structure features a double-decker cyclophane motif, stabilized by intramolecular π-dimerization of two delocalized benzidinium radical segments. Intermolecular π-dimers are formed in the solid state. Graphical abstract: [Figure not available: see fulltext.].
Biaryls, Crystal structure, Heterocycles, Oxidative coupling
0026-9247
Norrehed, Sara
f3df8490-6239-405c-90b9-b006449d03bb
Karlsson, Christoffer
527f7531-28b6-4c7f-a6ac-a281f357441a
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Thapper, Anders
80e1085c-040f-43bc-8a94-a603cb9a24f1
Huang, Ping
491809ae-968f-41fb-9f97-21d07cf403e1
Gogoll, Adolf
1769b3c3-6b75-496a-ac4b-89041c2d5126
Norrehed, Sara
f3df8490-6239-405c-90b9-b006449d03bb
Karlsson, Christoffer
527f7531-28b6-4c7f-a6ac-a281f357441a
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Thapper, Anders
80e1085c-040f-43bc-8a94-a603cb9a24f1
Huang, Ping
491809ae-968f-41fb-9f97-21d07cf403e1
Gogoll, Adolf
1769b3c3-6b75-496a-ac4b-89041c2d5126

Norrehed, Sara, Karlsson, Christoffer, Light, Mark E., Thapper, Anders, Huang, Ping and Gogoll, Adolf (2018) Formation of persistent organic diradicals from N,N′-diphenyl-3,7-diazacyclooctanes. Monatshefte für Chemie/Chemical Monthly. (doi:10.1007/s00706-018-2298-4).

Record type: Article

Abstract

N,N′-Diphenyl-3,7-diazacyclooctane and structurally related N,N′-diphenylbispidine derivatives react with silver(I) ions in a high-yielding C–C coupling reaction to produce dication–diradical species, with the silver ions serving a double function both as template and as an oxidant. The resulting bis(benzidino)phane derivatives are persistent organic radicals, stable for several months in solution as well as in the solid state, at room temperature and above, as well as being exposed to the atmosphere. The molecular structure features a double-decker cyclophane motif, stabilized by intramolecular π-dimerization of two delocalized benzidinium radical segments. Intermolecular π-dimers are formed in the solid state. Graphical abstract: [Figure not available: see fulltext.].

Text
2018-Monatshefte-Online First - Version of Record
Available under License Creative Commons Attribution.
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More information

Accepted/In Press date: 18 September 2018
e-pub ahead of print date: 29 October 2018
Keywords: Biaryls, Crystal structure, Heterocycles, Oxidative coupling

Identifiers

Local EPrints ID: 426182
URI: http://eprints.soton.ac.uk/id/eprint/426182
ISSN: 0026-9247
PURE UUID: 48ebc002-a92d-42b4-bd37-fa8159d78b2e
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 16 Nov 2018 17:30
Last modified: 18 Feb 2021 16:52

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Contributors

Author: Sara Norrehed
Author: Christoffer Karlsson
Author: Mark E. Light ORCID iD
Author: Anders Thapper
Author: Ping Huang
Author: Adolf Gogoll

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