Cyclotetrahalo-p-phenylenes: simulations of halogen substituted cycloparaphenylenes and their interaction with C60Electronic supplementary information (ESI) available. See DOI: 10.1039/c6cp03376h

Density functional calculations are used to study the role of edge-functionalization on the structure and electronic properties of cycloparaphenylene (CPPs) containing from six to twenty benzenoid rings. We substitute hydrogen by the halogens fluorine, chlorine and bromine. The resultant Cyclotetrah...

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Main Authors: Rio, J, Erbahar, D, Rayson, M, Briddon, P, Ewels, C. P
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Summary:Density functional calculations are used to study the role of edge-functionalization on the structure and electronic properties of cycloparaphenylene (CPPs) containing from six to twenty benzenoid rings. We substitute hydrogen by the halogens fluorine, chlorine and bromine. The resultant Cyclotetrahalo- p -phenylenes are compared with their hydrogenated equivalents, related linear paraphenyl and fluoro-paraphenyl polymers, and functionalised armchair edges in graphene nanoribbons. Notably we consider both structural and electronic evolution. Finally we examine C 60 @[10]CPP, i.e. C 60 encapsulated within [10]CPP, with the various ring terminations. The effect of halogenation on electronic level position around the gap strongly affects their capacity to form donor-acceptor pairs with fullerenes. Halogen substitution of cycloparaphenylenes ('nanohoops') shifts the HOMO and LUMO, for example eliminating redox coupling in the complex C 60 @[10]CPP-F.
ISSN:1463-9076
1463-9084
DOI:10.1039/c6cp03376h