Carbon Nanomaterials: Unique Tube–Ring Interactions: Complexation of Single‐Walled Carbon Nanotubes with Cycloparaphenyleneacetylenes (Small 26/2018)

Abstract

In article number https://doi.org/10.1002/smll.201800720, Koji Miki, Kouichi Ohe, and co‐workers report the “ring toss” method, throwing carbon nanorings onto carbon nanotubes, to prepare “tube‐in‐ring” supramolecular complexes. Carbon nanorings, [n]cycloparaphenyleneacetylenes, are utilized to demonstrate the formation of “tube‐in‐ring” complexes. The good size fit between the concave inner surface of the carbon nanorings and the convex outer surface of carbon nanotubes is important for the efficient production of rotaxane‐like complexes. This work provides a strategy to prepare interlocked carbon nanotubes for next‐generation electric devices and theranostic agents.

Interlocking of Single-Walled Carbon Nanotubes with Metal-Tethered Tetragonal Nanobrackets to Enrich a Few Hundredths of a Nanometer Range in Their Diameters

“…Mechanically interlocked CNTs have attracted considerable attention recently in view of tuning their mechanical and physical properties. CNTs have been interlocked by ring-closing olefin metathesis and thiol oxidation by de Juan and Pérez in 2014 and by Delius and Guldi in 2020, respectively, , and by threading a macrocycle by Miki and Ohe in 2018 . Since these cyclic molecules are either flexible in structure or ineffective for interlocking, they cannot be extended to CNT separation.…”

“…CNTs have been interlocked by ringclosing olefin metathesis and thiol oxidation by de Juan and Peŕez in 2014 and by Delius and Guldi in 2020, respectively, 27,28 and by threading a macrocycle by Miki and Ohe in 2018. 29 Since these cyclic molecules are either flexible in structure or ineffective for interlocking, they cannot be extended to CNT separation. Therefore, we designed a rigid tetragonal host molecule formed in situ in the presence of CNTs by tethering two square nanobrackets by metal coordination, securing both a rigidity in the structure and an opportunity for interlocking simultaneously.…”

Size-Selective Synthesis of Large Cycloparaphenyleneacetylene Carbon Nanohoops Using Alkyne Metathesis

“…Unfortunately, this reaction resulted in intractable yellow solids that were insoluble in organic solvents. This is contrasted by reports from Jasti, 20 Miki and Ohe, 32,33 who showed that other CPPA derivatives can be prepared in good yields using this method. In a separate experiment, we added SnCl 2 or H 2 SnCl 4 to a solution of [3]CPP 4 A or [3]CPP 5 A in THF.…”