A Pentacene-based Nanotube Displaying Enriched Electrochemical and Photochemical Activities

Kiyonori Kuroda, Kohei Yazaki, Yuya Tanaka, Munetaka Akita, Hayato Sakai, Taku Hasobe, Nikolai V. Tkachenko, Michito Yoshizawa

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Unlike previously well-studied, acyclic pentacene oligomers, the first synthesis of a cyclic pentacene trimer with a fixed tubular conformation is reported. A short-step synthesis starting from common pentacenequinone yielded the target molecule with a 1.5 nanometer length and a subnanometer pore. Steady-state spectroscopic analyses revealed that the close proximity of the non-conjugated, three pentacene chromophores allows the nanotube to display stepwise electrochemical/chemical oxidation characteristics. Furthermore, time-resolved transient absorption measurements elucidated the generation of an excited triplet state of the nanotube, with high quantum yield reaching about 180 % through intramolecular singlet fission and a very long triplet lifetime.

Original languageEnglish
JournalAngewandte Chemie - International Edition
DOIs
Publication statusAccepted/In press - 2018 Jan 1

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Keywords

  • macrocycles
  • nanotubes
  • pentacene
  • singlet fission
  • triplet states

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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