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Synthesis and characterization of a paramagnetic [2]rotaxane based on a crown ether-like wheel incorporating a nitroxide motif

Synthesis and characterization of a paramagnetic [2]rotaxane based on a crown ether-like wheel incorporating a nitroxide motif
Synthesis and characterization of a paramagnetic [2]rotaxane based on a crown ether-like wheel incorporating a nitroxide motif
The synthesis of a new nitroxide crown ether (8) and its use as the wheel in a bistable [2]rotaxane containing dialkylammonium and 4,4`-bipyridinium recognition sites, is reported. The synthesis of 8 was achieved by the sequential addition of substituted phenyl groups to nitrone derivatives leading to the preferential formation of the cis stereoisomer. Due to charge-dipolar interactions between the nitroxide unit and bipyridinium moiety, it was possible to probe the movement of the macrocycle between the two molecular stations of the [2]rotaxane after addition of a base by measuring the nitrogen hyperfine splittings in the corresponding EPR spectra. The equilibrium constant for the complexation of dibenzyl viologen by macrocycle 8 was also determined by EPR titration.
rotaxane, nitroxide, electron paramagnetic, resonance, spin probes, supramolceular chemistry
0947-6539
1198–1203
Bleve, Valentina
c7bf92c8-be45-4b7b-a326-09b55d32160f
Franchi, Paola
b8885c48-e4be-4cdb-b9e1-62bbe535f2be
Konstanteli, Evangelia
d0d16cd6-eef9-4432-bd16-1d9e78866281
Gualandi, Lorenzo
cd33c7c1-9072-4037-a627-8828aeb77e5b
Goldup, Stephen M.
0a93eedd-98bb-42c1-a963-e2815665e937
Mezzina, Elisabetta
f69e2f84-443c-4ddf-afa6-5bbb8ede5c83
Lucarini, Marco
b36ec433-d324-4788-81d4-6aaaa75035ce
Bleve, Valentina
c7bf92c8-be45-4b7b-a326-09b55d32160f
Franchi, Paola
b8885c48-e4be-4cdb-b9e1-62bbe535f2be
Konstanteli, Evangelia
d0d16cd6-eef9-4432-bd16-1d9e78866281
Gualandi, Lorenzo
cd33c7c1-9072-4037-a627-8828aeb77e5b
Goldup, Stephen M.
0a93eedd-98bb-42c1-a963-e2815665e937
Mezzina, Elisabetta
f69e2f84-443c-4ddf-afa6-5bbb8ede5c83
Lucarini, Marco
b36ec433-d324-4788-81d4-6aaaa75035ce

Bleve, Valentina, Franchi, Paola, Konstanteli, Evangelia, Gualandi, Lorenzo, Goldup, Stephen M., Mezzina, Elisabetta and Lucarini, Marco (2018) Synthesis and characterization of a paramagnetic [2]rotaxane based on a crown ether-like wheel incorporating a nitroxide motif. Chemistry - A European Journal, 24 (5), 1198–1203. (doi:10.1002/chem.201704969).

Record type: Article

Abstract

The synthesis of a new nitroxide crown ether (8) and its use as the wheel in a bistable [2]rotaxane containing dialkylammonium and 4,4`-bipyridinium recognition sites, is reported. The synthesis of 8 was achieved by the sequential addition of substituted phenyl groups to nitrone derivatives leading to the preferential formation of the cis stereoisomer. Due to charge-dipolar interactions between the nitroxide unit and bipyridinium moiety, it was possible to probe the movement of the macrocycle between the two molecular stations of the [2]rotaxane after addition of a base by measuring the nitrogen hyperfine splittings in the corresponding EPR spectra. The equilibrium constant for the complexation of dibenzyl viologen by macrocycle 8 was also determined by EPR titration.

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More information

Accepted/In Press date: 9 November 2017
e-pub ahead of print date: 10 November 2017
Published date: 24 January 2018
Keywords: rotaxane, nitroxide, electron paramagnetic, resonance, spin probes, supramolceular chemistry

Identifiers

Local EPrints ID: 416035
URI: https://eprints.soton.ac.uk/id/eprint/416035
ISSN: 0947-6539
PURE UUID: 22bac5a3-e7d6-420a-b6c6-b6b5b6617a20
ORCID for Stephen M. Goldup: ORCID iD orcid.org/0000-0003-3781-0464

Catalogue record

Date deposited: 30 Nov 2017 17:30
Last modified: 06 Jun 2018 12:22

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