A Pentacene‐based Nanotube Displaying Enriched Electrochemical and Photochemical Activities

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. S...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-01, Vol.58 (4), p.1115-1119
Main Authors: Kuroda, Kiyonori, Yazaki, Kohei, Tanaka, Yuya, Akita, Munetaka, Sakai, Hayato, Hasobe, Taku, Tkachenko, Nikolai V., Yoshizawa, Michito
Format: Article
Language:English
Subjects:
Atomic energy levels
Chemical synthesis
Chromophores
Conformation
Electrochemistry
macrocycles
Nanotubes
Oligomers
Organic chemistry
Oxidation
pentacene
Photochemicals
singlet fission
Trimers
Triplet state
triplet states
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Summary: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. A pentacene‐based nanotube was synthesized for the first time. The close proximity of the three non‐conjugated pentacene chromophores allows the nanotube to display stepwise electrochemical/chemical oxidation characteristics. Time‐resolved transient absorption measurements show the generation of an excited triplet state, with a high quantum yield (ca. 180 %) and very long triplet lifetime, through intramolecular singlet fission.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201812976