title: Simultaneous discrimination of handedness and diameter of single-walled carbon nanotubes (SWNTs) with chiral diporphyrin nanotweezers leading to enrichment of a single enantiomer of (6,5)-SWNTs.
abstract: Separation of single-walled carbon nanotubes (SWNTs) according to their handedness has been attracting growing interest. Our methodology to separate the enantiomers of SWNTs is based on molecular recognition with chiral diporphyrin nanotweezers. Herein, we report novel nanotweezers 1 consisting of two chiral porphyrins and phenanthrene in between. These nanotweezers 1 are rationally designed to discriminate diameter and handedness simultaneously by taking into account the relationship between the (n, m) selectivity and the structures of previously reported chiral nanotweezers. Owing to the relatively narrow cleft made by two porphyrins, the nanotweezers 1 showed high selectivity toward (6,5)-SWNTs possessing the smallest diameter among the major components of CoMoCAT-SWNTs. In addition, the chiral diporphyrin 1 discriminated the left- and right-handed structures of (6,5)-SWNTs, providing high enantiomeric excess (67% ee on the basis of the (6,5)-SWNTs with high optical purity recently reported by Weisman). In conclusion, only the single stereoisomer of (6,5)-SWNTs was highly enriched through the extraction of CoMoCAT-SWNTs with phenanthrene-bridged chiral diporphyrin nanotweezers 1.
authors.affiliation: Department of Chemistry, Shiga University of Medical Science, Seta, Otsu 520-2192, Japan.
authors.forename: Feng
authors.initials: F
authors.lastname: Wang
authors.forename: Kazunari
authors.initials: K
authors.lastname: Matsuda
authors.forename: A F M Mustafizur
authors.initials: AF
authors.lastname: Rahman
authors.forename: Xiaobin
authors.initials: X
authors.lastname: Peng
authors.forename: Takahide
authors.initials: T
authors.lastname: Kimura
authors.forename: Naoki
authors.initials: N
authors.lastname: Komatsu
mesh_terms: D003198:Computer Simulation; D008958:Models, Molecular; D015394:Molecular Structure; D037742:Nanotubes, Carbon / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010316:Particle Size; D010616:Phenanthrenes / Q000737:chemistry*; D011166:Porphyrins / Q000737:chemistry*; D013237:Stereoisomerism; D013499:Surface Properties; D015032:Zinc / Q000737:chemistry
chemical_list: D037742:Nanotubes, Carbon; D009942:Organometallic Compounds; D010616:Phenanthrenes; D011166:Porphyrins; C031181:phenanthrene; D015032:Zinc