Concise Synthesis and Facile Nanotube Assembly of a Symmetrically Multifunctionalized Cycloparaphenylene. Issue 52 (16th November 2015)

• Record Type: Journal Article
• Authors: Miyauchi, Yuta; Johmoto, Kohei; Yasuda, Nobuhiro; Uekusa, Hidehiro; Fujii, Shintaro; Kiguchi, Manabu; Ito, Hideto; Itami, Kenichiro; Tanaka, Ken
• Is Part Of: Chemistry. Volume 21:Issue 52(2015)
• Page Start: 18900
• Page End: 18904
• Publication Date: 2015-11-16
• Subjects: cycloparaphenylenes -- cyclotrimerization -- nanotubes -- rhodium -- self‐assembly; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201504185
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The concise synthesis of C 3 ‐symmetrical [12]CPP‐hexacarboxylate has been achieved through macrocyclization by the rhodium‐catalyzed intermolecular cross‐cyclotrimerization and subsequent reductive aromatization. C 3 ‐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. Abstract : Rhod to nanotubes ! The concise synthesis of a symmetrically multifunctionalized cycloparaphenylene (CPP), C 3 ‐symmetrical [12]CPP‐hexacarboxylate, has been achieved by rhodium‐catalyzed macrocyclization and subsequent reductive aromatization (see scheme). C 3 ‐Symmetrical functionalization of CPP with highly polar alkoxycarbonyl groups enabled the facile nanotube assembly on the flat solid surface as well as in the crystalline state.