Synthesis of Open-Cage Fullerene Derivatives Containing Multiple Hydroxyl and Amino Groups on the Rim of the Orifice†
Xueli Liu
Department of Chemistry, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, Inner Mongolia, 010021 China
Search for more papers by this authorRui Gao
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorZhen Liu
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorCorresponding Author
Jialin Ming
Department of Chemistry, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, Inner Mongolia, 010021 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorYi Qiu
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorCorresponding Author
Jie Su
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Liangbing Gan
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorXueli Liu
Department of Chemistry, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, Inner Mongolia, 010021 China
Search for more papers by this authorRui Gao
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorZhen Liu
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorCorresponding Author
Jialin Ming
Department of Chemistry, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, Inner Mongolia, 010021 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorYi Qiu
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorCorresponding Author
Jie Su
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Liangbing Gan
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorDedicated to the Special Issue of Recent Advances in Fullerene Chemistry.
Dedicated to Professor Shigeru Yamago on the occasion of his 60th birthday.
Comprehensive Summary
Most of the known open-cage fullerene derivatives contain carbonyl and other relatively inert groups on the rim of the orifice. It is difficult to rationally design further reactions and attach other functional groups on to these open-cage derivatives. In the present work, two molecules of difunctional 1,4-benzenediamine have been incorporated into the rim of an open-cage C60 derivative through one amino group leaving the other amino group free for further functionalization. The difunctional 4-aminophenol reacted analogously to form an open-cage derivative with a free OH group each on the two phenyl rings. The amino and hydroxyl groups on the phenyl ring above the rim of the orifice showed similar reactivity as aniline and phenol. One of the carbonyl groups on the rim of the orifice could be selectively reduced by NaBH4 and P(OEt)3. The reduction reactions were reversible and the reduced products could be readily converted back to the carbonyl precursor. Thus, this redox process acts as a tool to fine tune the size of the orifice for host-guest studies.
Supporting Information
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Appendix S1: Supporting Information |
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Citing Literature
15 June, 2023
Pages 1471-1477
