Novel macrocyclic dendrimers (Scheme 2), having two cis -1,3,5-cyclohexanetricarboxamide ( 1 ) or 1,3,5-benzenetricarboxamide units ( 3 ) in their core, were synthesized, and their self-assembly behaviors were evaluated in solution. Infrared spectroscopy of cis -1,3,5-cyclohexanetricarboxamide cored dendrimer ( 1 ) in CHCl 3 indicated that formation of strong hydrogen-bonding interactions is taking place among the core units. The 1 H NMR spectrum of 1 in CDCl 3 showed broadenings of all the peaks, which were sharpened by adding one drop of CF 3 CO 2 H. GPC analysis showed the formation of self-assembled particles having ultrahigh molecular weight, whose average diameter was evaluated as about 140 nm by DLS measurement. AFM observation of the cast on mica film showed that 1 forms a fibrous assembly of uniform thickness with a diameter of 6 nm. In sharp contrast to 1, 1,3,5-benzenetricarboxamide units cored dendrimer ( 3 ) did not form a fibrous assembly under identical conditions because of the twisted arrangement of the core units.
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Jang et al. (2004) studied this question.
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