Extremely strong tubular stacking of aromatic oligoamide macrocycles.

ABSTRACT: As the third-generation rigid macrocycles evolved from progenitor 1, cyclic aromatic oligoamides 3, with a backbone of reduced constraint, exhibit extremely strong stacking with an astoundingly high affinity (estimated lower limit of K_dimer > 10¹³ M^-1 in CHCl₃), which leads to dispersed tubular stacks that undergo further assembly in solution. Computational study reveals a very large binding energy (-49.77 kcal mol^-1) and indicates highly cooperative local dipole interactions that account for the observed strength and directionality for the stacking of 3. In the solid-state, X-ray diffraction (XRD) confirms that the aggregation of 3 results in well-aligned tubular stacks. The persistent tubular assemb

SUBMITTER: Kline MA 

PROVIDER: S-EPMC5424541 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature