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Updated: Apr 18, 2026

Synthesis and Characterization of Supramolecular Colloids
Published on: April 22, 2016
Isolation of a hydrogen-bonded complex based on the anthranol/anthroxyl pair: formation of a hydrogen-atom
Yasukazu Hirao1, Tohru Saito, Hiroyuki Kurata
1Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043 (Japan). y-hirao@chem.sci.osaka-u.ac.jp.
Abstract:
A hydrogen-bonded complex was successfully isolated as crystals from the anthranol/anthroxyl pair in the self-exchange proton-coupled electron transfer (PCET) reaction. The anthroxyl radical was stabilized by the introduction of a 9-anthryl group at the carbon atom at the 10-position. The hydrogen-bonded complex with anthranol self-assembled by π-π stacking to form a one-dimensional chain in the crystal. The conformation around the hydrogen bond was similar to that of the theoretically predicted PCET activated complex of the phenol/phenoxyl pair. X-ray crystal analyses revealed the self-exchange of a hydrogen atom via the hydrogen bond, indicating the activation of the self-exchange PCET reaction between anthranol and anthroxyl. Magnetic measurements revealed that magnetic ordering inside the one-dimensional chain caused the inactivation of the self-exchange reaction.
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