期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 140, 期 20, 页码 6336-6342出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b02327
关键词
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资金
- JSPS KAKENHI [JP16H06031, JP26102003, JP15K21721, JP15H00731, 17H05363]
- Tokuyama Science Foundation
- Global Research Laboratory through the National Research Foundation of Korea (NRF) - Ministry of Science, ICT (Information and Communication Technologies), and Future Planning [2013K1A1A2A02050183]
- Graduate School of Yonsei University
- [JP15J10528]
- National Research Foundation of Korea [2013K1A1A2A02050183] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
- Grants-in-Aid for Scientific Research [17H05363] Funding Source: KAKEN
We designed and synthesized molecular tweezers consisting of nitrogen-embedded buckybowl subunits. The judicious choice of the covalent linkers modulated their binding strength with C-60 or C-70 in solution. Titration studies by optical and H-1 NMR analyses revealed a 1:1 composition of the resulting complexes. X-ray diffraction analysis elucidated their solid-state structures, in which two azabuckybowl units surround one fullerene molecule. The large association constants stabilize the complexes toward redox reactions and the purification process on silica-gel column chromatography. The linker enabled tuning of the cavity size for binding of fullerenes, achieving complementary fullerene hosts for C-60 and C-70: the carbazole-bridged dimer preferentially associates with C-70 over C-60, while the phenanthrene-bridged dimer interacts with C-60 more strongly than C-70. Electrochemical analysis in combination with density functional theory calculations indicated the existence of intermolecular charge-transfer interactions between the buckybowl units and the fullerenes. Nonlinear optical measurements showed that the two-photon absorption cross sections of the molecular tweezers are enhanced upon association with fullerenes.
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