Issue 3, 2004
From the journal:

Organic & Biomolecular Chemistry

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

Glenn A. Burley,*a   Anthony G. Avent,a   Ilya V. Gol’dt,b   Peter B. Hitchcock,a   Hamad Al-Matar,c   Demis Paolucci,d   Francesco Paolucci,d   Patrick W. Fowler,e   Alessandro Soncini,e   Joan M. Streetf  and  Roger Taylor*a  

* Corresponding authors

a Chemistry Department, University of Sussex, Brighton, UK
E-mail: R.Taylor@sussex.ac.uk

b Chemistry Department, Moscow State University, Moscow 119899, Russia

c Chemistry Department, Faculty of Science, Kuwait University, Safat, Kuwait 13060

d Dipartimento di Chimica, Universitá di Bologna, 40126, Bologna, Italy

e Chemistry Department, University of Exeter, Stocker Road, Exeter, UK

f Chemistry Department, The University, Southampton, UK

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 18π 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.

Graphical abstract: Design and synthesis of multi-component 18π annulenic fluorofullerene ensembles suitable for donor–acceptor applications

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Article information

DOI
https://doi.org/10.1039/B309959H
Article type
Paper
Submitted
20 Aug 2003
Accepted
24 Nov 2003
First published
07 Jan 2004

Org. Biomol. Chem., 2004,2, 319-329

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

G. A. Burley, A. G. Avent, I. V. Gol’dt, P. B. Hitchcock, H. Al-Matar, D. Paolucci, F. Paolucci, P. W. Fowler, A. Soncini, J. M. Street and R. Taylor, Org. Biomol. Chem., 2004, 2, 319 DOI: 10.1039/B309959H

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