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Chemical Reduction of a Nanosized [6]Cyclo-2,7-naphthylene Macrocycle.

Zheng ZhouZheng WeiKoki IkemotoSota SatoHiroyuki IsobeMarina A Petrukhina
Published in: Angewandte Chemie (International ed. in English) (2021)
Chemical reduction of a naphthylene macrocycle, [6]cyclo-2,7-naphthylene ([6]CNAP, 1), with alkali metals, Li and K, revealed the accessibility of the doubly-reduced state of 1. The macrocyclic 12- anion was isolated in different coordination environments and crystallographically characterized. The single-crystal X-ray diffraction confirmed the formation of contact-ion complexes with one Li+ and two K+ ions in THF, and a "naked" dianion in the solvent-separated ion product with K+ ions in the presence of 18-crown-6 ether. The detailed structural analysis of 12- showed that the π-conjugation over the biaryl linkages between naphthylene panels were enhanced upon two-fold reduction, which was rationally explained by theoretical calculations.
Keyphrases
  • ionic liquid
  • quantum dots
  • high resolution
  • solid state
  • ion batteries
  • density functional theory
  • magnetic resonance
  • water soluble
  • computed tomography
  • human health
  • electron microscopy
  • climate change