Magnetically induced currents in [n]Cycloparaphenylenes, n = 6-11

Stefan Taubert, Dage Sundholm, Fabio Pichierri

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36 Citations (Scopus)

Abstract

We report calculations of the gauge-independent magnetically induced current densities in [n]cycloparaphenylenes ([n]CP), n = 6-11. In addition to the neutral [n]CPs, the dianion of [6]CP and the current densities of the corresponding metal complexes Li2[6]CP and Mg[6]CP are also investigated. By the ring current criterion, the [6]CP with 4n π electrons has a slight antiaromatic character, while [7]CP has (4n + 2) π electrons and is weakly aromatic with a ring current susceptibility strength that is about 25% of the ring current of benzene. The larger neutral [n]CPs, n = 8-11, do not sustain any net ring current around the nanohoop and are essentially nonaromatic. The weak paramagnetic ring current susceptibility of [6]CP flows along a 4n π pathway on either edge of the phenylene rings. For the dianions, the ring current susceptibility strengths are 24-35 nA/T diatropic and thus the addition of two electrons induces an electron delocalization and an aromatic character of the nanohoops. The dilithium complex of [6]CP with (4n + 2) π electrons is aromatic with a net ring current strength of 28 nA/T or 2.4 times the ring current strength of benzene, involving all 62 π electrons in the current pathway. The 1H NMR chemical shieldings and the nucleus-independent chemical shifts correlate with the strengths of the magnetically induced currents. The aromatic [n]cycloparaphenylenes have a quinoid structure, whereas the weakly aromatic or nonaromatic ones are benzoidic.

Original languageEnglish
Pages (from-to)5867-5874
Number of pages8
JournalJournal of Organic Chemistry
Volume75
Issue number17
DOIs
Publication statusPublished - 2010 Sep 3

ASJC Scopus subject areas

  • Organic Chemistry

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