Cyclotriveratrylene
(CTV) is a C
3-symmetrical
macrocycle, which can be used as a chiral building block in the construction
of supramolecular containers. Coupling of the CTV unit with a sucrose
molecule gave enantiopure water-soluble (after deprotection) containers.
The absolute configuration of the synthesized capsules was determined
by NMR and ECD spectroscopies and DFT calculations.
The synthesis of
four fluorescent diastereoisomeric molecular cages
containing cyclotriveratrylene and sucrose moieties connected
via
the naphthalene linkers is reported. These diastereoisomers
were found to be selective and efficient receptors for acetylcholine
and choline. Compound
P
-5a
has a better
affinity for choline over acetylcholine, while cage
M
-5a
exhibits a higher association constant for acetylcholine
over choline. The highest selectivity value was observed for compound
M
-5a
(
K
ACh
/
K
Ch
= 3.1). Cages
P
-5a
,
P
-5b
,
M
-5a
, and
M
-5b
were fully characterized
by the advanced NMR techniques, and ECD spectroscopy was supported
by DFT calculations. The binding constants
K
a
of these receptors were determined by fluorescence titration
experiments in acetonitrile.
Four diastereomeric molecular cages based on cyclotriveratrylene (CTV) and sucrose scaffolds, connected via p‐phenylene linkers, were synthesized in a few steps synthesis. The absolute configuration of these diastereoisomers was determined by advanced NMR and ECD spectroscopies supported by DFT calculations. The X‐Ray crystal structure of P‐4 b cage gave an insight into its unique structure. The binding properties of P‐4 a and M‐4 a cages towards small ammonium guests (1‐methylpyridinium and 1,3‐dimethylimidazolium salts) were investigated.
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