Abstract
The periodicity of two-dimensional entities can be manipulated by their stacking assembly, and incommensurate stacks of bilayers are attracting considerable interest in materials science. Stereoisomerism in incommensurate bilayers was first noted with incommensurate double-wall carbon nanotubes composed of helical carbon networks, but the lack of structural information hampered the chemical understanding such as the stereoselectivity during bilayer formation. In this study, we construct a finite molecular version of incommensurate carbon bilayers by assembling two helical cylindrical molecules in solution. An outer cylindrical molecule is designed to encapsulate a small-bore helical cylindrical molecule, and the spontaneous assembly of coaxial complexes proceeds in a stereoselective manner in solution with a preference for heterohelical combinations over diastereomeric, homohelical combinations. The rational design of incommensurate bilayers for material applications may be facilitated by the design and development of molecular versions with discrete structures with atomic precision.
Highlights
The periodicity of two-dimensional entities can be manipulated by their stacking assembly, and incommensurate stacks of bilayers are attracting considerable interest in materials science
The stereoisomerism originates from the twisted orientations of two graphitic layers, and the induced chirality and periodicity result in intriguing electronic properties1–3 Owing to the dimensionality reduction via facial discrimination, this unique type of stereoisomerism is easier to comprehend by rolling the carbon bilayers in the form of incommensurate double-wall carbon nanotubes (i-DWNTs
In summary, we report a molecular version of i-DWNT composed of incommensurate carbon bilayers
Summary
The periodicity of two-dimensional entities can be manipulated by their stacking assembly, and incommensurate stacks of bilayers are attracting considerable interest in materials science. Each of the diastereomeric orientations of the carbon bilayers gives rise to a set of enantiomer pairs; the coaxial assembly of incommensurate pairs of CNTs results in four stereoisomers of (P)/(P), (M)/(M), (P)/(M) and (M)/(P) for the double-wall combination of (20,4)- and (9,6)-CNTs7 Such stereoisomerism in carbon bilayers has long attracted attention, in the fields of physics and materials science, the structures have not been well understood and realised in a discrete form for molecular entities. For the assembly of i-DWNT complexes, heterohelical inner/outer combinations of (P)/(M) and (M)/(P) are preferred over homohelical combinations of (P)/(P) and (M)/(M) This is opposite of the suggestions made previously for infinite CNTs. We anticipate that the stereoselectivity observed with the incommensurate pairs of finite CNT molecules may facilitate the molecular design of chiral moiré patterns for materials applications
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