Cycloparaazine, a full-azine carbon nanoring

Till Drennhaus, Daiki Imoto, Elena S. Horst, Lena Lezius, Hiroki Shudo, Tomoki Kato, Klaus Bergander, Constantin G. Daniliuc, Dirk Leifert, Akiko Yagi (), Armido Studer () and Kenichiro Itami ()
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Till Drennhaus: Nagoya University
Daiki Imoto: Nagoya University
Elena S. Horst: Universität Münster
Lena Lezius: Universität Münster
Hiroki Shudo: Nagoya University
Tomoki Kato: Nagoya University
Klaus Bergander: Universität Münster
Constantin G. Daniliuc: Universität Münster
Dirk Leifert: Universität Münster
Akiko Yagi: Nagoya University
Armido Studer: Universität Münster
Kenichiro Itami: Nagoya University

Nature Communications, 2025, vol. 16, issue 1, 1-13

Abstract: Abstract Cycloparaphenylenes (CPPs) and related carbon nanorings (CNRs) represent iconic molecular entities in molecular nanocarbon science. While theoretical studies predict that the introduction of nitrogen atoms (N-doping) onto CPP frameworks would add a number of fascinating properties, only a handful of partially N-doped carbon nanorings have been synthesized. We herein report the synthesis of a long-awaited cycloparaazine (CPA), where every para-connected aromatic moiety consists of a N-heterocycle, and two other highly N-doped CNRs. The evaluation of optoelectronic and structural properties coupled with theoretical studies uncovered the impact of both the amount and positioning of N-doping onto the nanorings properties; far less ring strain, red-shifted UV–vis absorption and fluorescence, smaller HOMO–LUMO gaps and both higher reduction and oxidation potentials than pristine CPPs. Ultimately, new potential applications of highly N-doped nanorings were examined in non-covalent supramolecular property engineering with Lewis acids and as energy storage materials.

Date: 2025
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DOI: 10.1038/s41467-025-59934-5

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