Rational concept to recognize/extract single-Walled carbon nanotubes with a specific chirality

Hiroaki Ozawa, Tsuyohiko Fujigaya, Yasuro Niidome, Naosuke Hotta, Michiya Fujiki, Naotoshi Nakashima

Research output: Contribution to journalArticle

94 Citations (Scopus)

Abstract

Single-walled carbon nanotubes (SWNTs) have remarkable and unique electronic, mechanical, and thermal properties, which are closely related to their chiralities; thus, the chirality-selective recognition/extraction of the SWNTs is one of the central issues in nanotube science. However, any rational materials design enabling one to efficiently extract/solubilize pure SWNT with a desired chirality has yet not been demonstrated. Herein we report that certain chiral polyfluorene copolymers can well-recognize SWNTs with a certain chirality preferentially, leading to solubilization of specific chiral SWNTs. The chiral copolymers were prepared by the Ni0-catalyzed Yamamoto coupling reaction of 2,7-dibromo-9,9-di-n-decylfluorene and 2,7-dibromo-9,9-bis[(S)-(+)- 2-methylbutyl]fluorene comonomers. The selectivity of the SWNT chirality was mainly determined by the relative fraction of the achiral and chiral side groups. By a molecular mechanics simulation, the cooperative interaction between the fluorene moiety, alkyl side chain, and graphene wall were responsible for the recognition/dissolution ability of SWNT chirality. This is a first example describing the rational design and synthesis of novel fluorene-based copolymers toward the recognition/extraction of targeted (n,-m) chirality of the SWNTs.

Original languageEnglish
Pages (from-to)2651-2657
Number of pages7
JournalJournal of the American Chemical Society
Volume133
Issue number8
DOIs
Publication statusPublished - Mar 2 2011

Fingerprint

Carbon Nanotubes
Chirality
Single-walled carbon nanotubes (SWCN)
Copolymers
Nanotubes
Molecular mechanics
Graphite
Mechanics
Electronic properties
Graphene
Dissolution
Thermodynamic properties
Hot Temperature
Mechanical properties

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Rational concept to recognize/extract single-Walled carbon nanotubes with a specific chirality. / Ozawa, Hiroaki; Fujigaya, Tsuyohiko; Niidome, Yasuro; Hotta, Naosuke; Fujiki, Michiya; Nakashima, Naotoshi.

In: Journal of the American Chemical Society, Vol. 133, No. 8, 02.03.2011, p. 2651-2657.

Research output: Contribution to journalArticle

Ozawa, Hiroaki ; Fujigaya, Tsuyohiko ; Niidome, Yasuro ; Hotta, Naosuke ; Fujiki, Michiya ; Nakashima, Naotoshi. / Rational concept to recognize/extract single-Walled carbon nanotubes with a specific chirality. In: Journal of the American Chemical Society. 2011 ; Vol. 133, No. 8. pp. 2651-2657.
@article{73f2583f3e2b479795ad6a67f6b0d86d,
title = "Rational concept to recognize/extract single-Walled carbon nanotubes with a specific chirality",
abstract = "Single-walled carbon nanotubes (SWNTs) have remarkable and unique electronic, mechanical, and thermal properties, which are closely related to their chiralities; thus, the chirality-selective recognition/extraction of the SWNTs is one of the central issues in nanotube science. However, any rational materials design enabling one to efficiently extract/solubilize pure SWNT with a desired chirality has yet not been demonstrated. Herein we report that certain chiral polyfluorene copolymers can well-recognize SWNTs with a certain chirality preferentially, leading to solubilization of specific chiral SWNTs. The chiral copolymers were prepared by the Ni0-catalyzed Yamamoto coupling reaction of 2,7-dibromo-9,9-di-n-decylfluorene and 2,7-dibromo-9,9-bis[(S)-(+)- 2-methylbutyl]fluorene comonomers. The selectivity of the SWNT chirality was mainly determined by the relative fraction of the achiral and chiral side groups. By a molecular mechanics simulation, the cooperative interaction between the fluorene moiety, alkyl side chain, and graphene wall were responsible for the recognition/dissolution ability of SWNT chirality. This is a first example describing the rational design and synthesis of novel fluorene-based copolymers toward the recognition/extraction of targeted (n,-m) chirality of the SWNTs.",
author = "Hiroaki Ozawa and Tsuyohiko Fujigaya and Yasuro Niidome and Naosuke Hotta and Michiya Fujiki and Naotoshi Nakashima",
year = "2011",
month = "3",
day = "2",
doi = "10.1021/ja109399f",
language = "English",
volume = "133",
pages = "2651--2657",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "8",

}

TY - JOUR

T1 - Rational concept to recognize/extract single-Walled carbon nanotubes with a specific chirality

AU - Ozawa, Hiroaki

AU - Fujigaya, Tsuyohiko

AU - Niidome, Yasuro

AU - Hotta, Naosuke

AU - Fujiki, Michiya

AU - Nakashima, Naotoshi

PY - 2011/3/2

Y1 - 2011/3/2

N2 - Single-walled carbon nanotubes (SWNTs) have remarkable and unique electronic, mechanical, and thermal properties, which are closely related to their chiralities; thus, the chirality-selective recognition/extraction of the SWNTs is one of the central issues in nanotube science. However, any rational materials design enabling one to efficiently extract/solubilize pure SWNT with a desired chirality has yet not been demonstrated. Herein we report that certain chiral polyfluorene copolymers can well-recognize SWNTs with a certain chirality preferentially, leading to solubilization of specific chiral SWNTs. The chiral copolymers were prepared by the Ni0-catalyzed Yamamoto coupling reaction of 2,7-dibromo-9,9-di-n-decylfluorene and 2,7-dibromo-9,9-bis[(S)-(+)- 2-methylbutyl]fluorene comonomers. The selectivity of the SWNT chirality was mainly determined by the relative fraction of the achiral and chiral side groups. By a molecular mechanics simulation, the cooperative interaction between the fluorene moiety, alkyl side chain, and graphene wall were responsible for the recognition/dissolution ability of SWNT chirality. This is a first example describing the rational design and synthesis of novel fluorene-based copolymers toward the recognition/extraction of targeted (n,-m) chirality of the SWNTs.

AB - Single-walled carbon nanotubes (SWNTs) have remarkable and unique electronic, mechanical, and thermal properties, which are closely related to their chiralities; thus, the chirality-selective recognition/extraction of the SWNTs is one of the central issues in nanotube science. However, any rational materials design enabling one to efficiently extract/solubilize pure SWNT with a desired chirality has yet not been demonstrated. Herein we report that certain chiral polyfluorene copolymers can well-recognize SWNTs with a certain chirality preferentially, leading to solubilization of specific chiral SWNTs. The chiral copolymers were prepared by the Ni0-catalyzed Yamamoto coupling reaction of 2,7-dibromo-9,9-di-n-decylfluorene and 2,7-dibromo-9,9-bis[(S)-(+)- 2-methylbutyl]fluorene comonomers. The selectivity of the SWNT chirality was mainly determined by the relative fraction of the achiral and chiral side groups. By a molecular mechanics simulation, the cooperative interaction between the fluorene moiety, alkyl side chain, and graphene wall were responsible for the recognition/dissolution ability of SWNT chirality. This is a first example describing the rational design and synthesis of novel fluorene-based copolymers toward the recognition/extraction of targeted (n,-m) chirality of the SWNTs.

UR - http://www.scopus.com/inward/record.url?scp=79952272280&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79952272280&partnerID=8YFLogxK

U2 - 10.1021/ja109399f

DO - 10.1021/ja109399f

M3 - Article

VL - 133

SP - 2651

EP - 2657

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 8

ER -