Synthesis of Twisted [n]Cycloparaphenylene by Alkene Insertion
Tomoaki Terabayashi
Institute for Chemical Research, Kyoto University, Uji, 611-0011 Japan
Search for more papers by this authorCorresponding Author
Dr. Eiichi Kayahara
Institute for Chemical Research, Kyoto University, Uji, 611-0011 Japan
Search for more papers by this authorYichen Zhang
Institute for Chemical Research, Kyoto University, Uji, 611-0011 Japan
Search for more papers by this authorDr. Yoshiyuki Mizuhata
Institute for Chemical Research, Kyoto University, Uji, 611-0011 Japan
Search for more papers by this authorDr. Norihiro Tokitoh
Institute for Chemical Research, Kyoto University, Uji, 611-0011 Japan
Search for more papers by this authorProf. Dr. Tohru Nishinaga
Department of Chemistry, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397 Japan
Search for more papers by this authorProf. Dr. Tatsuhisa Kato
Institute for Chemical Research, Kyoto University, Uji, 611-0011 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Shigeru Yamago
Institute for Chemical Research, Kyoto University, Uji, 611-0011 Japan
Search for more papers by this authorTomoaki Terabayashi
Institute for Chemical Research, Kyoto University, Uji, 611-0011 Japan
Search for more papers by this authorCorresponding Author
Dr. Eiichi Kayahara
Institute for Chemical Research, Kyoto University, Uji, 611-0011 Japan
Search for more papers by this authorYichen Zhang
Institute for Chemical Research, Kyoto University, Uji, 611-0011 Japan
Search for more papers by this authorDr. Yoshiyuki Mizuhata
Institute for Chemical Research, Kyoto University, Uji, 611-0011 Japan
Search for more papers by this authorDr. Norihiro Tokitoh
Institute for Chemical Research, Kyoto University, Uji, 611-0011 Japan
Search for more papers by this authorProf. Dr. Tohru Nishinaga
Department of Chemistry, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397 Japan
Search for more papers by this authorProf. Dr. Tatsuhisa Kato
Institute for Chemical Research, Kyoto University, Uji, 611-0011 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Shigeru Yamago
Institute for Chemical Research, Kyoto University, Uji, 611-0011 Japan
Search for more papers by this authorAbstract
Mono-alkene-inserted [n]cycloparaphenylenes 1 [(ene)-[n]CPP] with n=6, 8, and 10, mono-ortho-phenylene-inserted [6]CPP 2, and di-alkene-insertved [n]CPP 3 [(ene)2-[n]CPP] with n=4, 6, and 8 were synthesized by fusing CPP precursors and alkene or ortho- phenylene groups through coupling reactions. Single-crystal X-ray diffraction analyses reveal that the strips formed by the π-surfaces of 1 and 2 exhibited a Möbius topology in the solid state. While the Möbius topology in the parent 1 and 2 in solution was lost due to the free rotation of the paraphenylene unit even at low temperatures, ene-[6]CPP 4 with eight 1-pyrrolyl groups preserved the Möbius topology even in solution. Despite a twist, 1 has in-plane conjugation and possesses a unique size dependence of the electronic properties: namely, the opposite size dependency of the HOMO–LUMO energy relative to conventional π-conjugated molecules.
Conflict of interest
The authors declare no conflict of interest.
Open Research
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