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

doi:10.1002/anie.201812976

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 journal › Article › Scientific › peer-review

13 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 language	English
Pages (from-to)	1115-1119
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	4
Early online date	2018
DOIs	https://doi.org/10.1002/anie.201812976
Publication status	Published - Jan 2019
Publication type	A1 Journal article-refereed

Keywords

macrocycles
nanotubes
pentacene
singlet fission
triplet states

Publication forum classification

Publication forum level 3

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201812976

Cite this

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title = "A Pentacene-based Nanotube Displaying Enriched Electrochemical and Photochemical Activities",

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.",

keywords = "macrocycles, nanotubes, pentacene, singlet fission, triplet states",

author = "Kiyonori Kuroda and Kohei Yazaki and Yuya Tanaka and Munetaka Akita and Hayato Sakai and Taku Hasobe and Tkachenko, {Nikolai V.} and Michito Yoshizawa",

year = "2019",

month = jan,

doi = "10.1002/anie.201812976",

language = "English",

volume = "58",

pages = "1115--1119",

journal = "Angewandte Chemie (International Edition)",

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T1 - A Pentacene-based Nanotube Displaying Enriched Electrochemical and Photochemical Activities

AU - Kuroda, Kiyonori

AU - Yazaki, Kohei

AU - Tanaka, Yuya

AU - Akita, Munetaka

AU - Sakai, Hayato

AU - Hasobe, Taku

AU - Tkachenko, Nikolai V.

AU - Yoshizawa, Michito

PY - 2019/1

Y1 - 2019/1

N2 - 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.

AB - 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.

KW - macrocycles

KW - nanotubes

KW - pentacene

KW - singlet fission

KW - triplet states

U2 - 10.1002/anie.201812976

DO - 10.1002/anie.201812976

M3 - Article

AN - SCOPUS:85059193866

SN - 1433-7851

VL - 58

SP - 1115

EP - 1119

JO - Angewandte Chemie (International Edition)

JF - Angewandte Chemie (International Edition)

IS - 4

ER -

A Pentacene-based Nanotube Displaying Enriched Electrochemical and Photochemical Activities

Abstract

Keywords

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