Pillar[6]quinone: facile synthesis, crystal structures and electrochemical properties

Tomoki Hirohata; Naoki Shida; Hidehiro Uekusa; Nobuhiro Yasuda; Hirotomo Nishihara; Tomoki Ogoshi; Ikuyoshi Tomita; Shinsuke Inagi

doi:10.1039/d1cc02413b

Pillar[6]quinone: facile synthesis, crystal structures and electrochemical properties

Chem Commun (Camb). 2021 Jun 29;57(52):6360-6363. doi: 10.1039/d1cc02413b.

Authors

Tomoki Hirohata¹, Naoki Shida¹, Hidehiro Uekusa², Nobuhiro Yasuda³, Hirotomo Nishihara⁴, Tomoki Ogoshi⁵, Ikuyoshi Tomita¹, Shinsuke Inagi⁶

Affiliations

¹ Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8502, Japan. inagi@cap.mac.titech.ac.jp.
² Department of Chemistry, School of Science, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo 152-8551, Japan.
³ Diffraction and Scattering Division, Japan Synchrotron Radiation Research Institute, 1-1-1, Kouto, Sayo-cho, Sayo-gun, Hyogo 679-5198, Japan.
⁴ Advanced Institute for Materials Research (WPI-AIMR)/Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1, Katahira, Aoba-ku, Sendai 980-8577, Japan.
⁵ Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
⁶ Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8502, Japan. inagi@cap.mac.titech.ac.jp and PRESTO, Japan Science and Technology Agency (JST), 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.

PMID: 34105536
DOI: 10.1039/d1cc02413b

Abstract

A novel electron-deficient macrocycle, pillar[6]quinone (P[Q]6), has been synthesized for the first time by both chemical and electrochemical oxidation of pillar[6]arene, showing clear hexagonal columnar stacking in the solid state. Cathodic voltammetric studies of P[Q]6 revealed that three electrons are injected first, followed by stepwise one-electron reductions.