Self-Assembly and Fluorescence Properties of [60]Fullerene-Pentacene Monoadducts

Kentaro Kubo; Tomoyuki Tajima; Hitoshi Shirai; Takuya Nishihama; Yutaka Takaguchi

doi:10.1002/slct.201602074

Self-Assembly and Fluorescence Properties of [60]Fullerene-Pentacene Monoadducts

Kentaro Kubo, Tomoyuki Tajima, Hitoshi Shirai, Takuya Nishihama, Yutaka Takaguchi

Research output: Contribution to journal › Article › peer-review

Abstract

The highly soluble [60]fullerene-pentacene monoadducts 2 a and 2 b were synthesized by a Diels-Alder reaction between [60]fullerene and pentacene derivatives. The single-crystal X-ray diffraction analysis of 2 a revealed an attractive intermolecular interaction between [60]fullerene moiety of one molecule and the pentacene arms of an adjacent molecule, resulting in the formation of head-to-tail dimers in solution. This self-association behavior of 2 a and 2 b was also observed by ¹H NMR and fluorescence spectroscopy in chloroform. Both the excitation and emission wavelengths can be modulated via the concentration of 2 a and 2 b.

Original language	English
Pages (from-to)	2452-2456
Number of pages	5
Journal	ChemistrySelect
Volume	2
Issue number	8
DOIs	https://doi.org/10.1002/slct.201602074
Publication status	Published - Mar 13 2017

Keywords

Fluorescence
Fullerenes
Host-guest systems
π-interactions

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1002/slct.201602074

Cite this

@article{2584f9b037014b54bf06eb140b7e5102,

title = "Self-Assembly and Fluorescence Properties of [60]Fullerene-Pentacene Monoadducts",

abstract = "The highly soluble [60]fullerene-pentacene monoadducts 2 a and 2 b were synthesized by a Diels-Alder reaction between [60]fullerene and pentacene derivatives. The single-crystal X-ray diffraction analysis of 2 a revealed an attractive intermolecular interaction between [60]fullerene moiety of one molecule and the pentacene arms of an adjacent molecule, resulting in the formation of head-to-tail dimers in solution. This self-association behavior of 2 a and 2 b was also observed by 1H NMR and fluorescence spectroscopy in chloroform. Both the excitation and emission wavelengths can be modulated via the concentration of 2 a and 2 b.",

keywords = "Fluorescence, Fullerenes, Host-guest systems, π-interactions",

author = "Kentaro Kubo and Tomoyuki Tajima and Hitoshi Shirai and Takuya Nishihama and Yutaka Takaguchi",

note = "Funding Information: This work was partially supported by JSPS KAKENHI grants 15H03519 (Y.T.) and 16 K05895 (T.T.). Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

month = mar,

day = "13",

doi = "10.1002/slct.201602074",

language = "English",

volume = "2",

pages = "2452--2456",

journal = "ChemistrySelect",

issn = "2365-6549",

publisher = "Wiley-Blackwell Publishing Ltd",

number = "8",

}

TY - JOUR

T1 - Self-Assembly and Fluorescence Properties of [60]Fullerene-Pentacene Monoadducts

AU - Kubo, Kentaro

AU - Tajima, Tomoyuki

AU - Shirai, Hitoshi

AU - Nishihama, Takuya

AU - Takaguchi, Yutaka

PY - 2017/3/13

Y1 - 2017/3/13

N2 - The highly soluble [60]fullerene-pentacene monoadducts 2 a and 2 b were synthesized by a Diels-Alder reaction between [60]fullerene and pentacene derivatives. The single-crystal X-ray diffraction analysis of 2 a revealed an attractive intermolecular interaction between [60]fullerene moiety of one molecule and the pentacene arms of an adjacent molecule, resulting in the formation of head-to-tail dimers in solution. This self-association behavior of 2 a and 2 b was also observed by 1H NMR and fluorescence spectroscopy in chloroform. Both the excitation and emission wavelengths can be modulated via the concentration of 2 a and 2 b.

AB - The highly soluble [60]fullerene-pentacene monoadducts 2 a and 2 b were synthesized by a Diels-Alder reaction between [60]fullerene and pentacene derivatives. The single-crystal X-ray diffraction analysis of 2 a revealed an attractive intermolecular interaction between [60]fullerene moiety of one molecule and the pentacene arms of an adjacent molecule, resulting in the formation of head-to-tail dimers in solution. This self-association behavior of 2 a and 2 b was also observed by 1H NMR and fluorescence spectroscopy in chloroform. Both the excitation and emission wavelengths can be modulated via the concentration of 2 a and 2 b.

KW - Fluorescence

KW - Fullerenes

KW - Host-guest systems

KW - π-interactions

UR - http://www.scopus.com/inward/record.url?scp=85041746215&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85041746215&partnerID=8YFLogxK

U2 - 10.1002/slct.201602074

DO - 10.1002/slct.201602074

M3 - Article

AN - SCOPUS:85041746215

SN - 2365-6549

VL - 2

SP - 2452

EP - 2456

JO - ChemistrySelect

JF - ChemistrySelect

IS - 8

ER -

Self-Assembly and Fluorescence Properties of [60]Fullerene-Pentacene Monoadducts

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this