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Complexation of diquat by disubstituted dibenzo-30-crown-10 derivatives

✍ Scribed by Franz H. Kohnke; J. Fraser Stoddart; Billy L. Allwood; David J. Williams


Book ID
104228736
Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
325 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis


X-Ray structural investigations of the 1:l crystaZZine conpZexes formed between [Diquat][PFg]2 and (i) the bisformyZ dibenzo-30-crown-10 derivative 2 and (ii) the dimethyl dibenzo-30-crown-10 derivative 4 reveal that in both eases, charge transfer, as weZZ as electrostatic binding and weak [C--H-.. 01 hydrogen bonding combine to give the complexes their remarkable stabilities; in acetone solution, the stability constants for the I:1 eonpZexes invoZving 2, 3, and 4 are 2100, 50000, and 48000 WI, respeetiveZy. Recently, we described 2 an eight-step synthesis of the macrobicyclic receptor molecule 1 and showed that this host molecule encapsulates the diquat 3 dication in both the solid state 2,4 and in solution . Two disubstituted dibenzo-30-crown-10 derivatives, 2 and 3 (i.e. the


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Dynamic 'H n.m.r spectroscopy reveals that the disubstituted derivatives 2 -4 of dibenzo-30-crown-10 (51 form strong I:1 complexes in CD3COCD3 solution with the diquat dication. Desyrrunetrisation of the guest by the bound host provides the key to a novel application of this form of spectroscopic an