Large N-Doped Zigzag Hydrocarbon Belts from Calixarenes: Synthesis, Structure, and Properties
Yi Peng
MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Mei-Ling Tan
MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.
Search for more papers by this authorKe-Xing Ma
MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Shuo Tong
MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084 China
E-mail: [email protected]; [email protected]
Search for more papers by this authorCorresponding Author
Prof. Dr. Mei-Xiang Wang
MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084 China
E-mail: [email protected]; [email protected]
Search for more papers by this authorYi Peng
MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Mei-Ling Tan
MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.
Search for more papers by this authorKe-Xing Ma
MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Shuo Tong
MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084 China
E-mail: [email protected]; [email protected]
Search for more papers by this authorCorresponding Author
Prof. Dr. Mei-Xiang Wang
MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084 China
E-mail: [email protected]; [email protected]
Search for more papers by this authorThis is dedicated to Prof. Jieping Zhu on the occasion of his 60th birthday
Abstract
Zigzag hydrocarbon belts and heteroatom-doped analogs have captivated chemists because of their unique structures, tantalizing properties, and potential applications. Despite synthetic breakthroughs, the diversity, especially, the size of belts synthesized by fjord-stitching approach is limited by resorcin[n]arenes (n = 4, 6). We report herein the synthesis, structure and properties of large belts starting from conventional calix[8]arenes. The synthesis features multiple C─N cross-coupling reactions of per-brominated calix[8]arenes with anilines and ammonia, and selective transformation of 1,4-dihydroquinoline into quinolin-4(1H)-one segments. The molecules in question adopt a unique zigzag belt structure with nitrogen atoms and functional groups located around both portals, yielding a large octagonal prism cavity. They are able to accommodate fullerene C60 or C70 with high affinity driven by lone-pair electron/π interactions and steric complementarity between host and guest.
Conflict of Interests
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the Supporting Information of this article.
Supporting Information
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| ange202509916-sup-0001-SupMat.pdf13.7 MB | Supporting Information |
| ange202509916-sup-0002-SupMat.zip8 MB | Supporting Information |
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