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Optimization and Insights into the Mechanism of Formation of Mechanically Interlocked Derivatives of Single‐Walled Carbon Nanotubes
Author(s) -
de Juan Alberto,
Mar Bernal M.,
Pérez Emilio M.
Publication year - 2015
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201500115
Subject(s) - catenane , carbon nanotube , molecule , catalysis , materials science , nanotechnology , metathesis , chemistry , chemical engineering , organic chemistry , polymer , polymerization , composite material , engineering
The mechanical bond provides a stable yet dynamic link between the submolecular components of mechanically interlocked molecules, such as rotaxanes and catenanes. We introduced the mechanical bond as a new tool for the chemical modification of single‐walled carbon nanotubes (SWNTs), producing the first mechanically interlocked derivatives of nanotubes (MINTs). To do so, we used U‐shaped molecules featuring two units of a SWNT‐recognition unit, which were cyclized around the SWNT by means of ring‐closing metathesis (RCM). Here we report optimized conditions for the synthesis of MINTs obtained by systematic investigation of the effect of the concentration of the U‐shaped molecule 1 , reaction time, and catalyst concentration. Analysis of the data also provides insights into the mechanism of formation of MINTs. In particular, the effect of the concentration of 1 supports the formation of a 1⋅ SWNT complex. The kinetic data follow a pseudo‐first‐order behavior that validates the RCM as the rate‐determining step. An excess of RCM catalyst leads to the formation of supramolecularly adsorbed linear oligomers of 1 .