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.
Bibliographical noteFunding 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.
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All Science Journal Classification (ASJC) codes
- Organic Chemistry