title: Quantitative self-assembly of a purely organic three-dimensional catenane in water.
abstract: Self-assembly by means of coordinative bond formation has opened up opportunities for the high-yield synthesis of molecules with complex topologies. However, the preparation of purely covalent molecular architectures in aqueous media has remained a challenging task. Here, we present the preparation of a three-dimensional catenane through a self-assembly process that relies on the formation of dynamic hydrazone linkages in an acidic aqueous medium. The quantitative synthesis process and the mechanically interlocked structure of the resulting catenane were established by NMR spectroscopy, mass spectrometry, X-ray crystallography and HPLC studies. In addition, the labile hydrazone linkages of the individual [2]catenane components may be 'locked' by increasing the pH of the solution, yielding a relatively kinetically stable molecule. The present study thus details a simple approach to the creation and control of complex molecular architectures under reaction conditions that mimic biological milieux.
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou 310027, China.|Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: Hao
authors.initials: H
authors.lastname: Li
authors.affiliation: Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: Huacheng
authors.initials: H
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: Aaron D
authors.initials: AD
authors.lastname: Lammer
authors.affiliation: Department of Chemistry and Biochemistry &Materials Science, Engineering, and Commercialization Program, Texas State University, San Macros, Texas 78666, USA.
authors.forename: Ming
authors.initials: M
authors.lastname: Wang
authors.affiliation: Department of Chemistry and Biochemistry &Materials Science, Engineering, and Commercialization Program, Texas State University, San Macros, Texas 78666, USA.
authors.forename: Xiaopeng
authors.initials: X
authors.lastname: Li
authors.affiliation: Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: Vincent M
authors.initials: VM
authors.lastname: Lynch
authors.affiliation: Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, USA.|Department of Chemistry, Innovative Drug Research Center, and School of Materials Science and Engineering, Shanghai University, Shanghai 200444, China.
authors.forename: Jonathan L
authors.initials: JL
authors.lastname: Sessler
mesh_terms: D000873:Anthracenes / Q000737:chemistry*; D056148:Chromatography, Reverse-Phase; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D014867:Water / Q000737:chemistry*
chemical_list: D000873:Anthracenes; C467767:catenane; D014867:Water