Friedel–Crafts Acylation for Accessing Multi-Bridge-Functionalized Large Pillar[n]arenes
Dr. Tan-Hao Shi
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, 615-8510 Kyoto, Japan
Search for more papers by this authorProf. Dr. Shigehisa Akine
WPI Nano Life Science Institute (WPI-NanoLSI), Kanazawa University, Kakuma-machi, 920-1192 Kanazawa, Ishikawa, Japan
Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, 920-1192 Kanazawa, Ishikawa, Japan
Search for more papers by this authorDr. Shunsuke Ohtani
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, 615-8510 Kyoto, Japan
Search for more papers by this authorDr. Kenichi Kato
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, 615-8510 Kyoto, Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Tomoki Ogoshi
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, 615-8510 Kyoto, Japan
WPI Nano Life Science Institute (WPI-NanoLSI), Kanazawa University, Kakuma-machi, 920-1192 Kanazawa, Ishikawa, Japan
Search for more papers by this authorDr. Tan-Hao Shi
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, 615-8510 Kyoto, Japan
Search for more papers by this authorProf. Dr. Shigehisa Akine
WPI Nano Life Science Institute (WPI-NanoLSI), Kanazawa University, Kakuma-machi, 920-1192 Kanazawa, Ishikawa, Japan
Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, 920-1192 Kanazawa, Ishikawa, Japan
Search for more papers by this authorDr. Shunsuke Ohtani
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, 615-8510 Kyoto, Japan
Search for more papers by this authorDr. Kenichi Kato
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, 615-8510 Kyoto, Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Tomoki Ogoshi
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, 615-8510 Kyoto, Japan
WPI Nano Life Science Institute (WPI-NanoLSI), Kanazawa University, Kakuma-machi, 920-1192 Kanazawa, Ishikawa, Japan
Search for more papers by this authorAbstract
Pillar[n]arenes can be constructed using a Friedel–Crafts alkylation process. However, due to the reversible nature of the alkylation, mixture of large pillar[n]arenes (n≥7) are obtained as minor products, and thus laborious purification are necessary to isolate the larger pillar[n]arenes. Moreover, inert methylene bridges are introduced during the alkylation process, and the multi-functionalization of the bridges has never been investigated. Herein, an irreversible Friedel–Crafts acylation is used to prepare pillar[n]arenes. Due to the irreversible nature of the acylation, the reaction of precursors bearing carboxylic acids and electron-rich arene rings results in a size-exclusive formation of pillar[n]arenes, in which the ring-size is determined by the precursor length. Because of this size-selective formation, laborious separation of undesired macrocycles is not necessary. Moreover, the bridges of pillar[n]arenes are selectively installed with reactive carbonyl groups using the acylation method, whose positions are determined by the precursor used. The carbonyl bridges can be easily converted into versatile functional groups, leading to various laterally modified pillar[n]arenes, which cannot be accessed by the alkylation strategy.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
Supporting Information
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| ange202318268-sup-0001-trans-11.cif3.7 MB | Supporting Information |
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