A Saturn-Like Complex Composed of Macrocyclic Oligothiophene and C60 Fullerene: Structure, Stability, and Photophysical Properties in Solution and the Solid State

Hideyuki Shimizu; Kyu Hyung Park; Hiroyuki Otani; Shinobu Aoyagi; Tohru Nishinaga; Yoshio Aso; Dongho Kim; Masahiko Iyoda

doi:10.1002/chem.201705565

A Saturn-Like Complex Composed of Macrocyclic Oligothiophene and C₆₀ Fullerene: Structure, Stability, and Photophysical Properties in Solution and the Solid State

Hideyuki Shimizu, Kyu Hyung Park, Hiroyuki Otani, Shinobu Aoyagi, Tohru Nishinaga, Yoshio Aso, Dongho Kim, Masahiko Iyoda

Department of Chemistry

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

17 Citations (Scopus)

Abstract

A Saturn-like 1:1 complex composed of macrocyclic oligothiophene E-8T7A and C₆₀ fullerene (C₆₀) was synthesized to investigate the interaction between macrocyclic oligothiophenes and C₆₀ in solution and the solid state. Because the Saturn-like 1:1 complex E-8T7A⋅C₆₀ is mainly stabilized by van der Waals interactions between C₆₀ and the sulfur atoms of the E-8T7A macrocycle, C₆₀ is rather weakly incorporated inside the macro-ring in solution. However, in the solid state the Saturn-like 1:1 complex preferentially formed single crystals or nanostructured polymorphs. Interestingly, X-ray analysis and theoretical calculations exhibited hindered rotation of C₆₀ in the Saturn-like complex due to interactions between C₆₀ and the sulfur atoms. Furthermore, the photoinduced charge transfer (CT) interaction between E-8T7A and C₆₀ in solution was investigated by using femtosecond transient absorption (TA) spectroscopy. The ultrafast TA spectral changes in the photoinduced absorption bands were attributed to the CT process in the Saturn-like structure.

Original language	English
Pages (from-to)	3793-3801
Number of pages	9
Journal	Chemistry - A European Journal
Volume	24
Issue number	15
DOIs	https://doi.org/10.1002/chem.201705565
Publication status	Published - 2018 Mar 12

Bibliographical note

Funding Information:
The work at Tokyo Metropolitan University was supported by the Grants-in-Aid for Scientific Research (26288040), Japanese Society for the Promotion of Science (JSPS) and partly performed under the Cooperative Research Program of the “Network Joint Research Center for Materials and Devices” (M.I.). The synchrotron radiation experiments were performed at SPring-8 with the approval of the Japan Synchrotron Radiation Research Institute (JASRI) (Proposal No. 2016B1432). We thank Dr. Hiroyasu Sato (Rigaku Corporation) for the X-ray analysis of E-8T7A, and Mr. Toshihiro Fujiwara for his experimental assistance. The research at Yonsei University was supported by the Global Research Laboratory (GRL) Program (2013K1A1A2A02050183) of the Ministry of Education, Science, and Technology (MEST) of Korea.

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

Access to Document

10.1002/chem.201705565

Cite this

@article{c831294db7ce438592fecfc9f02696f8,

title = "A Saturn-Like Complex Composed of Macrocyclic Oligothiophene and C60 Fullerene: Structure, Stability, and Photophysical Properties in Solution and the Solid State",

abstract = "A Saturn-like 1:1 complex composed of macrocyclic oligothiophene E-8T7A and C60 fullerene (C60) was synthesized to investigate the interaction between macrocyclic oligothiophenes and C60 in solution and the solid state. Because the Saturn-like 1:1 complex E-8T7A⋅C60 is mainly stabilized by van der Waals interactions between C60 and the sulfur atoms of the E-8T7A macrocycle, C60 is rather weakly incorporated inside the macro-ring in solution. However, in the solid state the Saturn-like 1:1 complex preferentially formed single crystals or nanostructured polymorphs. Interestingly, X-ray analysis and theoretical calculations exhibited hindered rotation of C60 in the Saturn-like complex due to interactions between C60 and the sulfur atoms. Furthermore, the photoinduced charge transfer (CT) interaction between E-8T7A and C60 in solution was investigated by using femtosecond transient absorption (TA) spectroscopy. The ultrafast TA spectral changes in the photoinduced absorption bands were attributed to the CT process in the Saturn-like structure.",

author = "Hideyuki Shimizu and Park, {Kyu Hyung} and Hiroyuki Otani and Shinobu Aoyagi and Tohru Nishinaga and Yoshio Aso and Dongho Kim and Masahiko Iyoda",

note = "Funding Information: The work at Tokyo Metropolitan University was supported by the Grants-in-Aid for Scientific Research (26288040), Japanese Society for the Promotion of Science (JSPS) and partly performed under the Cooperative Research Program of the “Network Joint Research Center for Materials and Devices” (M.I.). The synchrotron radiation experiments were performed at SPring-8 with the approval of the Japan Synchrotron Radiation Research Institute (JASRI) (Proposal No. 2016B1432). We thank Dr. Hiroyasu Sato (Rigaku Corporation) for the X-ray analysis of E-8T7A, and Mr. Toshihiro Fujiwara for his experimental assistance. The research at Yonsei University was supported by the Global Research Laboratory (GRL) Program (2013K1A1A2A02050183) of the Ministry of Education, Science, and Technology (MEST) of Korea. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

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language = "English",

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A Saturn-Like Complex Composed of Macrocyclic Oligothiophene and C₆₀ Fullerene: Structure, Stability, and Photophysical Properties in Solution and the Solid State. / Shimizu, Hideyuki; Park, Kyu Hyung; Otani, Hiroyuki et al.
In: Chemistry - A European Journal, Vol. 24, No. 15, 12.03.2018, p. 3793-3801.

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

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T1 - A Saturn-Like Complex Composed of Macrocyclic Oligothiophene and C60 Fullerene

T2 - Structure, Stability, and Photophysical Properties in Solution and the Solid State

AU - Shimizu, Hideyuki

AU - Park, Kyu Hyung

AU - Otani, Hiroyuki

AU - Aoyagi, Shinobu

AU - Nishinaga, Tohru

AU - Aso, Yoshio

AU - Kim, Dongho

AU - Iyoda, Masahiko

N1 - Funding Information: The work at Tokyo Metropolitan University was supported by the Grants-in-Aid for Scientific Research (26288040), Japanese Society for the Promotion of Science (JSPS) and partly performed under the Cooperative Research Program of the “Network Joint Research Center for Materials and Devices” (M.I.). The synchrotron radiation experiments were performed at SPring-8 with the approval of the Japan Synchrotron Radiation Research Institute (JASRI) (Proposal No. 2016B1432). We thank Dr. Hiroyasu Sato (Rigaku Corporation) for the X-ray analysis of E-8T7A, and Mr. Toshihiro Fujiwara for his experimental assistance. The research at Yonsei University was supported by the Global Research Laboratory (GRL) Program (2013K1A1A2A02050183) of the Ministry of Education, Science, and Technology (MEST) of Korea. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/3/12

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N2 - A Saturn-like 1:1 complex composed of macrocyclic oligothiophene E-8T7A and C60 fullerene (C60) was synthesized to investigate the interaction between macrocyclic oligothiophenes and C60 in solution and the solid state. Because the Saturn-like 1:1 complex E-8T7A⋅C60 is mainly stabilized by van der Waals interactions between C60 and the sulfur atoms of the E-8T7A macrocycle, C60 is rather weakly incorporated inside the macro-ring in solution. However, in the solid state the Saturn-like 1:1 complex preferentially formed single crystals or nanostructured polymorphs. Interestingly, X-ray analysis and theoretical calculations exhibited hindered rotation of C60 in the Saturn-like complex due to interactions between C60 and the sulfur atoms. Furthermore, the photoinduced charge transfer (CT) interaction between E-8T7A and C60 in solution was investigated by using femtosecond transient absorption (TA) spectroscopy. The ultrafast TA spectral changes in the photoinduced absorption bands were attributed to the CT process in the Saturn-like structure.

AB - A Saturn-like 1:1 complex composed of macrocyclic oligothiophene E-8T7A and C60 fullerene (C60) was synthesized to investigate the interaction between macrocyclic oligothiophenes and C60 in solution and the solid state. Because the Saturn-like 1:1 complex E-8T7A⋅C60 is mainly stabilized by van der Waals interactions between C60 and the sulfur atoms of the E-8T7A macrocycle, C60 is rather weakly incorporated inside the macro-ring in solution. However, in the solid state the Saturn-like 1:1 complex preferentially formed single crystals or nanostructured polymorphs. Interestingly, X-ray analysis and theoretical calculations exhibited hindered rotation of C60 in the Saturn-like complex due to interactions between C60 and the sulfur atoms. Furthermore, the photoinduced charge transfer (CT) interaction between E-8T7A and C60 in solution was investigated by using femtosecond transient absorption (TA) spectroscopy. The ultrafast TA spectral changes in the photoinduced absorption bands were attributed to the CT process in the Saturn-like structure.

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