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A solid state intramolecular Wittig reaction enables efficient synthesis of endofullerenes including Ne@C60, 3He@C60 and HD@C60

A solid state intramolecular Wittig reaction enables efficient synthesis of endofullerenes including Ne@C60, 3He@C60 and HD@C60
A solid state intramolecular Wittig reaction enables efficient synthesis of endofullerenes including Ne@C60, 3He@C60 and HD@C60
An open‐cage fullerene incorporating phosphorous ylid and carbonyl group moieties on the rim of the orifice can be filled with gases (H2, He, Ne) in the solid state, and the cage opening then contracted in situ by raising the temperature to complete an intramolecular Wittig reaction, trapping the atom or molecule inside. Known transformations complete conversion of the product fullerene to C60 containing the endohedral species. As well as providing an improved synthesis of large quantities of 4He@C60, H2@C60 and D2@C60, the method allows the efficient incorporation of expensive gases such as HD and 3He, to prepare HD@C60 and 3He@C60. The method also enables the first synthesis of Ne@C60 by molecular surgery, and its characterization by crystallography and 13C NMR spectroscopy.
endohedral fullerene, phosphorus ylid, X-ray diffraction, NMR spectroscopy, synthetic methods
1433-7851
8960-8966
Hoffman, Gabriela
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Walkey, Mark C.
432139de-52cb-4e28-9ad0-b254e0523775
Gräsvik, John
28699f13-0e49-49f5-b1e6-540f342096b3
Bacanu, George R.
181f3a56-e8da-445f-b9c6-c8ead171433f
Alom, Shamim
f6b56fb1-7f94-432a-87cd-887f6e5d9f64
Bloodworth, Sally
943160fc-1b70-4c29-b2e3-b7785cee8a0c
Light, Mark E.
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Levitt, Malcolm H.
bcc5a80a-e5c5-4e0e-9a9a-249d036747c3
Whitby, Richard John
45632236-ab00-4ad0-a02d-6209043e818b
Hoffman, Gabriela
8b98ba1c-ee09-4922-82e4-a9240aa12e64
Walkey, Mark C.
432139de-52cb-4e28-9ad0-b254e0523775
Gräsvik, John
28699f13-0e49-49f5-b1e6-540f342096b3
Bacanu, George R.
181f3a56-e8da-445f-b9c6-c8ead171433f
Alom, Shamim
f6b56fb1-7f94-432a-87cd-887f6e5d9f64
Bloodworth, Sally
943160fc-1b70-4c29-b2e3-b7785cee8a0c
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Levitt, Malcolm H.
bcc5a80a-e5c5-4e0e-9a9a-249d036747c3
Whitby, Richard John
45632236-ab00-4ad0-a02d-6209043e818b

Hoffman, Gabriela, Walkey, Mark C., Gräsvik, John, Bacanu, George R., Alom, Shamim, Bloodworth, Sally, Light, Mark E., Levitt, Malcolm H. and Whitby, Richard John (2021) A solid state intramolecular Wittig reaction enables efficient synthesis of endofullerenes including Ne@C60, 3He@C60 and HD@C60. Angewandte Chemie International Edition, 60 (16), 8960-8966. (doi:10.1002/anie.202100817).

Record type: Article

Abstract

An open‐cage fullerene incorporating phosphorous ylid and carbonyl group moieties on the rim of the orifice can be filled with gases (H2, He, Ne) in the solid state, and the cage opening then contracted in situ by raising the temperature to complete an intramolecular Wittig reaction, trapping the atom or molecule inside. Known transformations complete conversion of the product fullerene to C60 containing the endohedral species. As well as providing an improved synthesis of large quantities of 4He@C60, H2@C60 and D2@C60, the method allows the efficient incorporation of expensive gases such as HD and 3He, to prepare HD@C60 and 3He@C60. The method also enables the first synthesis of Ne@C60 by molecular surgery, and its characterization by crystallography and 13C NMR spectroscopy.

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e-pub ahead of print date: 7 February 2021
Keywords: endohedral fullerene, phosphorus ylid, X-ray diffraction, NMR spectroscopy, synthetic methods

Identifiers

Local EPrints ID: 447547
URI: http://eprints.soton.ac.uk/id/eprint/447547
ISSN: 1433-7851
PURE UUID: 4f510d81-4463-4ef2-bec6-eeeaf5f79e24
ORCID for Sally Bloodworth: ORCID iD orcid.org/0000-0003-2219-3635
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Malcolm H. Levitt: ORCID iD orcid.org/0000-0001-9878-1180
ORCID for Richard John Whitby: ORCID iD orcid.org/0000-0002-9891-5502

Catalogue record

Date deposited: 15 Mar 2021 17:41
Last modified: 26 Nov 2021 02:45

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Contributors

Author: Gabriela Hoffman
Author: Mark C. Walkey
Author: John Gräsvik
Author: George R. Bacanu
Author: Shamim Alom
Author: Mark E. Light ORCID iD

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