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<p>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 <i>para</i>-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.</p>

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Cycloparaazine, a full-azine carbon nanoring

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年6月9日

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  • Till Drennhaus,
  • Daiki Imoto,
  • Elena S. Horst,
  • Lena Lezius,
  • Hiroki Shudo,
  • Tomoki Kato,
  • Klaus Bergander,
  • Constantin G. Daniliuc,
  • Dirk Leifert,
  • Akiko Yagi,
  • Armido Studer,
  • Kenichiro Itami

摘要

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.