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Concise Synthesis and Facile Nanotube Assembly of a Symmetrically Multifunctionalized Cycloparaphenylene
Authors:Yuta Miyauchi  Dr. Kohei Johmoto  Dr. Nobuhiro Yasuda  Prof. Dr. Hidehiro Uekusa  Dr. Shintaro Fujii  Prof. Dr. Manabu Kiguchi  Dr. Hideto Ito  Prof. Dr. Kenichiro Itami  Prof. Dr. Ken Tanaka
Affiliation:1. Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, O‐okayama, Meguro‐ku, Tokyo 152‐8550 (Japan) http://www.apc.titech.ac.jp/~ktanaka/;2. Department of Chemistry and Materials Science, Graduate School of Science and Engineering, Tokyo Institute of Technology, O‐okayama, Meguro‐ku, Tokyo 152‐8551 (Japan);3. Japan Science and Technology Agency, CREST, 4‐1‐8 Honcho, Kawaguchi, Saitama 332‐0012 (Japan);4. Japan Synchrotron Radiation Research Institute/SPring‐8, 1‐1‐1 Kouto, Sayo‐cho, Sayo‐gun, Hyogo 679‐5198 (Japan);5. Department of Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology O‐okayama, Meguro‐ku, Tokyo 152‐8551 (Japan);6. Institute of Transformative Bio‐Molecules (WPI‐ITbM) and Graduate School of Science, Nagoya University, Chikusa, Nagoya 464‐8602 (Japan);7. Japan Science and Technology Agency, ERATO, Itami Molecular Nanocarbon Project, Nagoya University, Chikusa, Nagoya 464‐8602 (Japan)
Abstract:The concise synthesis of C3‐symmetrical [12]CPP‐hexacarboxylate has been achieved through macrocyclization by the rhodium‐catalyzed intermolecular cross‐cyclotrimerization and subsequent reductive aromatization. C3‐Symmetrical functionalization of CPP with highly polar alkoxycarbonyl groups enabled the structurally uniform nanotube assembly in the crystalline state through multiple hydrogen‐bonding interactions giving a dimer followed by one‐dimensional stacking.
Keywords:cycloparaphenylenes  cyclotrimerization  nanotubes  rhodium  self‐assembly
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