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A Pentacene‐based Nanotube Displaying Enriched Electrochemical and Photochemical Activities
Author(s) -
Kuroda Kiyonori,
Yazaki Kohei,
Tanaka Yuya,
Akita Munetaka,
Sakai Hayato,
Hasobe Taku,
Tkachenko Nikolai V.,
Yoshizawa Michito
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201812976
Subject(s) - pentacene , trimer , nanotube , chromophore , photochemistry , singlet fission , intramolecular force , excited state , chemistry , ultrafast laser spectroscopy , molecule , conjugated system , electrochemistry , materials science , quantum yield , nanotechnology , dimer , triplet state , spectroscopy , carbon nanotube , stereochemistry , fluorescence , organic chemistry , polymer , layer (electronics) , quantum mechanics , nuclear physics , physics , electrode , thin film transistor
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.