The University of Southampton
University of Southampton Institutional Repository

Porphyrinoid rotaxanes: Building a mechanical picket fence

Porphyrinoid rotaxanes: Building a mechanical picket fence
Porphyrinoid rotaxanes: Building a mechanical picket fence
Building on recent progress in the synthesis of functional porphyrins for a range of applications using the Cu-mediated azide–alkyne cycloaddition (CuAAC) reaction, we describe the active template CuAAC synthesis of interlocked triazole functionalised porphyrinoids in excellent yield. By synthesising interlocked analogues of previously studied porphyrin–corrole conjugates, we demonstrate that this approach gives access to rotaxanes in which the detailed electronic properties of the axle component are unchanged but whose steric properties are transformed by the mechanical “picket fence” provided by the threaded rings. Our results suggest that interlocked functionalised porphyrins, readily available using the AT-CuAAC approach, are sterically hindered scaffolds for the development of new catalysts and materials.
1478-6524
6679-6685
Ngo, Thien Huynh
a6697de9-4b83-4eeb-b516-e05b33cc437a
Labuta, Jan
54af3cc4-f269-4331-b98a-028e4711f493
Lim, Gary N.
a4a74fe3-24ba-4e6f-857f-c5ced7864cfa
Webre, W.
35a90ada-d9fb-4b6b-8a8d-936812b77de2
D'Souza, Francis
0d85ba80-3481-423a-895b-50fadb631f9a
Karr, Paul A.
8272674b-4ea4-456e-85f6-9b63078e69f0
Lewis, James E.M.
42b46a03-a7ca-4d3a-96e5-a5c962fc9573
Hill, Jonathan P.
5f936d50-22d4-447c-ba9c-e9721a414077
Ariga, Katsuhiko
d368003c-164f-4f22-a61e-919336ac87dd
Goldup, Stephen
0a93eedd-98bb-42c1-a963-e2815665e937
Ngo, Thien Huynh
a6697de9-4b83-4eeb-b516-e05b33cc437a
Labuta, Jan
54af3cc4-f269-4331-b98a-028e4711f493
Lim, Gary N.
a4a74fe3-24ba-4e6f-857f-c5ced7864cfa
Webre, W.
35a90ada-d9fb-4b6b-8a8d-936812b77de2
D'Souza, Francis
0d85ba80-3481-423a-895b-50fadb631f9a
Karr, Paul A.
8272674b-4ea4-456e-85f6-9b63078e69f0
Lewis, James E.M.
42b46a03-a7ca-4d3a-96e5-a5c962fc9573
Hill, Jonathan P.
5f936d50-22d4-447c-ba9c-e9721a414077
Ariga, Katsuhiko
d368003c-164f-4f22-a61e-919336ac87dd
Goldup, Stephen
0a93eedd-98bb-42c1-a963-e2815665e937

Ngo, Thien Huynh, Labuta, Jan, Lim, Gary N., Webre, W., D'Souza, Francis, Karr, Paul A., Lewis, James E.M., Hill, Jonathan P., Ariga, Katsuhiko and Goldup, Stephen (2017) Porphyrinoid rotaxanes: Building a mechanical picket fence. Chemical Science, 8 (9), 6679-6685. (doi:10.1039/C7SC03165C).

Record type: Article

Abstract

Building on recent progress in the synthesis of functional porphyrins for a range of applications using the Cu-mediated azide–alkyne cycloaddition (CuAAC) reaction, we describe the active template CuAAC synthesis of interlocked triazole functionalised porphyrinoids in excellent yield. By synthesising interlocked analogues of previously studied porphyrin–corrole conjugates, we demonstrate that this approach gives access to rotaxanes in which the detailed electronic properties of the axle component are unchanged but whose steric properties are transformed by the mechanical “picket fence” provided by the threaded rings. Our results suggest that interlocked functionalised porphyrins, readily available using the AT-CuAAC approach, are sterically hindered scaffolds for the development of new catalysts and materials.

Text
rvsd MS Ngo Porphyrin Chem Sci - Accepted Manuscript
Available under License Creative Commons Attribution.
Download (2MB)

More information

Accepted/In Press date: 3 August 2017
e-pub ahead of print date: 4 August 2017
Published date: 1 September 2017

Identifiers

Local EPrints ID: 412998
URI: https://eprints.soton.ac.uk/id/eprint/412998
ISSN: 1478-6524
PURE UUID: 8826514d-67d0-42e2-907a-25b11e04a610
ORCID for Stephen Goldup: ORCID iD orcid.org/0000-0003-3781-0464

Catalogue record

Date deposited: 10 Aug 2017 16:30
Last modified: 14 Mar 2019 01:33

Export record

Altmetrics

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 https://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.

×