Nygaard et al.
SCHEME 1. Complexation of TTF by CBPQT4+
valent interactions that take place between the different com-
ponents in bistable [2]catenanes and [2]rotaxanes in order to
improve future design. The inclusion of TTF derivatives inside
the cavity of CBPQT4+ is well documented7 and leads to the
formation of pseudorotaxanes12 under thermodynamic control
upon mixing of their acyclic and cyclic components in solution
and several research groups has investigated the green 1:1
complex formed (Scheme 1) between CBPQT4+ and different
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TTF derivatives.13,14 It has been concluded7e that the strength
of the binding between TTF derivatives and CBPQT4+ is
strongly dependent on the π-electron-donating ability of the TTF
derivatives. Thus, the better is the π-electron donor, the stronger
is the complex formed with CBPQT4+. Other studies5g,15,16 have
shown that addition of ethylene glycol substituents to the TTF
unit enhance the binding constant with the CBPQT4+ host by
up to 2 orders of magnitude by virtue of their entering into
[C-H‚‚‚O] hydrogen bonding interactions with some of the
R-CH hydrogen atoms in the bipyridinium units of CBPQT4+
.
Consequently, there seems to be two major sets of noncovalent
interactions one needs to take into account when the strength
of the binding between CBPQT4+ and a TTF unit bearing
ethylene glycol substituents is considered, namely (i) π-π and
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1618 J. Org. Chem., Vol. 72, No. 5, 2007