Norcorroles as antiaromatic π-electronic systems that form dimension-controlled assemblies

Soh Ishikawa; Kazuhisa Yamasumi; Shinya Sugiura; Shunsuke Sato; Go Watanabe; Yun Hee Koo; Shu Seki; Yuya Bando; Yohei Haketa; Hiroshi Shinokubo; Hiromitsu Maeda

doi:10.1039/D4SC01633E

Norcorroles as antiaromatic π-electronic systems that form dimension-controlled assemblies†

Soh Ishikawa,^a Kazuhisa Yamasumi,^a Shinya Sugiura,^a Shunsuke Sato,^b Go Watanabe,

^bc Yun Hee Koo,^d Shu Seki,

^d Yuya Bando,^a Yohei Haketa,

^a Hiroshi Shinokubo

^e and Hiromitsu Maeda

*^a

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* Corresponding authors

^a Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, Kusatsu 525-8577, Japan
E-mail: maedahir@ph.ritsumei.ac.jp

^b Department of Physics, School of Science, Kitasato University, Sagamihara 252-0373, Japan

^c Department of Data Science, School of Frontier Engineering, Kitasato University, Sagamihara 252-0373, Japan

^d Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan

^e Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8603, Japan

Abstract

Norcorrole derivatives with 3,4,5-trialkoxyphenyl moieties at the meso positions were synthesized to form various stacking assemblies in single crystals and thermotropic liquid crystals (LCs) depending on aliphatic chain lengths. Triple-decker stacking structures were formed via the interactions between the antiaromatic systems formed for the butoxy and dodecyloxy derivatives in the single-crystal and LC states, respectively. In particular, the LC state exhibited discotic columnar structures comprising triple deckers to exhibit high electric conductivity, as supported by molecular dynamics simulations.

Chemical Science

Norcorroles as antiaromatic π-electronic systems that form dimension-controlled assemblies†

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