Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2022 Jul 12

PMID 35819871

Authors

Rakesh Kumar

Piotr J Chmielewski

Tadeusz Lis

Dirk Volkmer

Marcin Stepien

Affiliations

Soon will be listed here.

Abstract

Tridecacyclene tetraimide, TCTI, an electron-deficient non-benzenoid nanocarbon with a C N polycyclic framework was obtained in a concise synthesis. TCTI has a non-planar structure and forms π-stacked dimers in the solid state. In solution, it undergoes eight single-electron reductions, yielding a range of negatively charged states up to an octaanion. Except for the latter species, which has a remarkably large electronic gap, the anions feature extended near-infrared absorptions, with a particularly strong band at 1692 nm observed for the dianion. A computational analysis of the TCTI anions shows that their stability originates from the combined effects of electron-deficient imide groups and the local aromaticity of reduced acenaphthylene units. The properties of TCTI make it potentially useful in electrochromic and charge storage applications.

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