The University of Southampton
University of Southampton Institutional Repository

Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores

Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores
Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores

The high yielding CuI-mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the CuI catalyst leads to the adventitious and usually undesirable insertion of Cu ions into any non-metalated porphyrinoid centers during reaction. Here we report a "sacrificial rotaxane"strategy for the multifunctionalization of porphyrins with free base corroles without incidental copper insertion. This strategy can be considered a general method for implementing CuI-mediated click reactions with metal cation sequestration to avoid detrimental effects caused by the presence of copper cations. This journal is

1359-7345
7447-7450
Ngo, Huynh Thien
64af0972-5c76-4a68-a519-70dd53f4d088
Lewis, James E.M.
42b46a03-a7ca-4d3a-96e5-a5c962fc9573
Payne, Daniel T.
039a42c3-6a7e-4043-a389-0faa23f4744a
D'Souza, Francis
a38c4d90-b830-44d2-9586-44a8edb55d5c
Hill, Jonathan P.
5f936d50-22d4-447c-ba9c-e9721a414077
Ariga, Katsuhiko
d368003c-164f-4f22-a61e-919336ac87dd
Yoshikawa, Genki
f4094cf9-3315-4870-8a76-c7af8299c0fd
Goldup, Stephen M.
0a93eedd-98bb-42c1-a963-e2815665e937
Ngo, Huynh Thien
64af0972-5c76-4a68-a519-70dd53f4d088
Lewis, James E.M.
42b46a03-a7ca-4d3a-96e5-a5c962fc9573
Payne, Daniel T.
039a42c3-6a7e-4043-a389-0faa23f4744a
D'Souza, Francis
a38c4d90-b830-44d2-9586-44a8edb55d5c
Hill, Jonathan P.
5f936d50-22d4-447c-ba9c-e9721a414077
Ariga, Katsuhiko
d368003c-164f-4f22-a61e-919336ac87dd
Yoshikawa, Genki
f4094cf9-3315-4870-8a76-c7af8299c0fd
Goldup, Stephen M.
0a93eedd-98bb-42c1-a963-e2815665e937

Ngo, Huynh Thien, Lewis, James E.M., Payne, Daniel T., D'Souza, Francis, Hill, Jonathan P., Ariga, Katsuhiko, Yoshikawa, Genki and Goldup, Stephen M. (2020) Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores. Chemical Communications, 56 (54), 7447-7450. (doi:10.1039/c9cc09681g).

Record type: Article

Abstract

The high yielding CuI-mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the CuI catalyst leads to the adventitious and usually undesirable insertion of Cu ions into any non-metalated porphyrinoid centers during reaction. Here we report a "sacrificial rotaxane"strategy for the multifunctionalization of porphyrins with free base corroles without incidental copper insertion. This strategy can be considered a general method for implementing CuI-mediated click reactions with metal cation sequestration to avoid detrimental effects caused by the presence of copper cations. This journal is

Text
Chemcommun_Revised - Accepted Manuscript
Download (1MB)

More information

Accepted/In Press date: 26 May 2020
Published date: 11 July 2020

Identifiers

Local EPrints ID: 442836
URI: http://eprints.soton.ac.uk/id/eprint/442836
ISSN: 1359-7345
PURE UUID: e1c464d3-70bf-4c2e-96ed-6150a9acbd8f
ORCID for Stephen M. Goldup: ORCID iD orcid.org/0000-0003-3781-0464

Catalogue record

Date deposited: 28 Jul 2020 16:41
Last modified: 10 Jun 2022 04:03

Export record

Altmetrics

Contributors

Author: Huynh Thien Ngo
Author: James E.M. Lewis
Author: Daniel T. Payne
Author: Francis D'Souza
Author: Jonathan P. Hill
Author: Katsuhiko Ariga
Author: Genki Yoshikawa

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×