Acyclic Cucurbit[<i>n</i>]uril Molecular
Containers Selectively Solubilize Single-Walled Carbon Nanotubes in
Water
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Abstract
Making single-walled carbon nanotubes (SWNTs) soluble
in water
is a challenging first step to use their remarkable electronic and
optical properties in a variety of applications. We report that acyclic
cucurbit[<i>n</i>]uril molecular containers <b>1</b> and <b>2</b> selectively solubilize small-diameter and low
chiral angle SWNTs. The selectivity is tunable by increasing the concentration
of the molecular containers or by adjusting the ionic strength of
the solution. Even at a concentration 1000 times lower than typically
required for surfactants, the molecular containers render SWNTs soluble
in water. Molecular mechanics simulations suggest that these C-shaped
acyclic molecules complex the SWNTs such that a large portion of nanotube
sidewalls are exposed to the external environment. These “naked”
nanotubes fluoresce upon patching the exposed surface with sodium
dodecylbenzene sulfonate