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Design and synthesis of multi-component 18 ? annulenic fluorofullerene ensembles suitable for donor-acceptor applications

Design and synthesis of multi-component 18 ? annulenic fluorofullerene ensembles suitable for donor-acceptor applications
Design and synthesis of multi-component 18 ? annulenic fluorofullerene ensembles suitable for donor-acceptor applications
A series of trannulene (all-trans annulene) derivatives of [60]fullerene have been prepared by reacting C60F18 with methanetricarboxylate esters that incorporate a range of photoactive functions. All the compounds have the intense emerald-green colour of fullerene trannulenes, characterised by strong bands at ca. 612 and 667 nm. Single crystal X-ray studies show that the packing varies with the nature of the addend, attributable to differing steric effects. UV/vis absorption spectra display transitions of the respective fullerene and addend models, indicating absence of electronic interactions between them in the ground state. These now provide an extensive series for testing photoactive (light-harvesting) properties, with the exceptional properties of having strong visible light absorption. Their exceptional stability is attributed to the 18? aromatic circuit, inability to undergo nucleophilic substitution without disrupting this circuit, and a curved cage region that is shielded to reagents by the three bulky addends.
electron-transfer, building-blocks, fullerene, c60f18, derivatives, chemistry, systems, energy, c-60
1477-0520
319-329
Burley, Glenn A.
ccedea82-73a7-454b-b718-b2d6a56ca28b
Avent, Anthony G.
6fe5d51d-5f31-454f-938a-ec91c840f2ce
Gol'dt, Ilya V.
92aef798-e0b7-4dea-a3b5-178093f24ce8
Hitchcock, Peter B.
4c0fe381-c3e8-452c-a284-fe14acd3b748
Al-Matar, Hamad
de0c4543-cb45-4497-8938-9af00130d898
Paolucci, Demis
9157555c-1792-4a4b-b9a3-1cc4d17cc6df
Paolucci, Francesco
073b630d-7adc-41ee-b198-6b33bcacce6c
Fowler, Patrick W.
59aba48d-43b5-4898-99ef-c2512337970c
Soncini, Alessandro
3fd14e1b-96eb-4440-a136-ae4d15599208
Street, Joan M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6
Burley, Glenn A.
ccedea82-73a7-454b-b718-b2d6a56ca28b
Avent, Anthony G.
6fe5d51d-5f31-454f-938a-ec91c840f2ce
Gol'dt, Ilya V.
92aef798-e0b7-4dea-a3b5-178093f24ce8
Hitchcock, Peter B.
4c0fe381-c3e8-452c-a284-fe14acd3b748
Al-Matar, Hamad
de0c4543-cb45-4497-8938-9af00130d898
Paolucci, Demis
9157555c-1792-4a4b-b9a3-1cc4d17cc6df
Paolucci, Francesco
073b630d-7adc-41ee-b198-6b33bcacce6c
Fowler, Patrick W.
59aba48d-43b5-4898-99ef-c2512337970c
Soncini, Alessandro
3fd14e1b-96eb-4440-a136-ae4d15599208
Street, Joan M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6

Burley, Glenn A., Avent, Anthony G., Gol'dt, Ilya V., Hitchcock, Peter B., Al-Matar, Hamad, Paolucci, Demis, Paolucci, Francesco, Fowler, Patrick W., Soncini, Alessandro, Street, Joan M. and Taylor, Roger (2004) Design and synthesis of multi-component 18 ? annulenic fluorofullerene ensembles suitable for donor-acceptor applications. Organic and Biomolecular Chemistry, 2 (3), 319-329. (doi:10.1039/b309959h).

Record type: Article

Abstract

A series of trannulene (all-trans annulene) derivatives of [60]fullerene have been prepared by reacting C60F18 with methanetricarboxylate esters that incorporate a range of photoactive functions. All the compounds have the intense emerald-green colour of fullerene trannulenes, characterised by strong bands at ca. 612 and 667 nm. Single crystal X-ray studies show that the packing varies with the nature of the addend, attributable to differing steric effects. UV/vis absorption spectra display transitions of the respective fullerene and addend models, indicating absence of electronic interactions between them in the ground state. These now provide an extensive series for testing photoactive (light-harvesting) properties, with the exceptional properties of having strong visible light absorption. Their exceptional stability is attributed to the 18? aromatic circuit, inability to undergo nucleophilic substitution without disrupting this circuit, and a curved cage region that is shielded to reagents by the three bulky addends.

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More information

Published date: 7 February 2004
Keywords: electron-transfer, building-blocks, fullerene, c60f18, derivatives, chemistry, systems, energy, c-60

Identifiers

Local EPrints ID: 20150
URI: https://eprints.soton.ac.uk/id/eprint/20150
ISSN: 1477-0520
PURE UUID: 7edf43bc-d498-4145-94cc-8e3b0e12f99c

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Date deposited: 22 Feb 2006
Last modified: 17 Jul 2017 16:29

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Contributors

Author: Glenn A. Burley
Author: Anthony G. Avent
Author: Ilya V. Gol'dt
Author: Peter B. Hitchcock
Author: Hamad Al-Matar
Author: Demis Paolucci
Author: Francesco Paolucci
Author: Patrick W. Fowler
Author: Alessandro Soncini
Author: Joan M. Street
Author: Roger Taylor

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