Template-directed synthesis of mechanically interlocked molecular bundles using dynamic covalent chemistry

BH Northrop, F Aricó, N Tangchiavang, JD Badjić… - Organic …, 2006 - ACS Publications
BH Northrop, F Aricó, N Tangchiavang, JD Badjić, JF Stoddart
Organic Letters, 2006ACS Publications
Mixing the dipyrido [24] crown-8 derivatives carrying one or two formyl group (s) on the 4
position (s) of their pyridine ring (s) with a 3-fold symmetrical trisammonium ion template in a
3: 1 ratio in CD3NO2 results in the formation of thermodynamically stable [4]
pseudorotaxanes which, upon addition of a 1, 3, 5-trisaminobenzene cap, form mechanically
interlocked molecular bundles with one and two caps, respectively, by virtue of dynamic
imine bond formation.
Mixing the dipyrido[24]crown-8 derivatives carrying one or two formyl group(s) on the 4 position(s) of their pyridine ring(s) with a 3-fold symmetrical trisammonium ion template in a 3:1 ratio in CD3NO2 results in the formation of thermodynamically stable [4]pseudorotaxanes which, upon addition of a 1,3,5-trisaminobenzene cap, form mechanically interlocked molecular bundles with one and two caps, respectively, by virtue of dynamic imine bond formation.
ACS Publications
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