Carbazole-cored phenyl isoxazolyl benzenes possessing chiral moieties were synthesized. The molecules selfassembled to form stacked supramolecular assemblies in an isodesmic fashion in chloroform, whereas the molecules preferably assembled in a cooperative fashion in methylcyclohexane (MCH), which was determined by spectroscopic methods, including UV− vis absorption, fluorescence, and 1 H NMR spectroscopy. Clear nucleation and elongation processes were observed in the plot of the degree of aggregation (α agg ) against temperature, which allowed us to determine the elongation temperature (T e ), the enthalpic gain in the elongation process (ΔH e ), the equilibrium constant between nucleation and elongation (K a ), and the degree of polymerization at the elongation temperature ([N n (T e )]). Circular dichroism (CD) and circularly polarized luminescence (CPL) studies revealed the formation of helically stacked assemblies in solution. Moreover, the majority-rule effect was clearly observed in the solutions of mixtures of (S)-and (R)-1, indicating the chiral amplification behavior of the helically stacked assemblies consisting of (S)-and (R)-1. AFM provided morphological insight into the assemblies on mica, which clearly indicates the formation of polymeric assemblies in the solid state.
Ureido-pyrimidinone (UPy)-appended tris(phenylisoxazolyl)benzenes were synthesized. The UPy moieties of the tris(phenylisoxazolyl)benzenes stably formed self-complementary dimers in solution. The dimers self-assembled to form helically twisted stacking constructs driven by π-π stacking...
Three carbo[5]helicenes
([5]CHs) containing benzylmaleimide groups displayed columnar stacked
organizations, including dislocated, parallel, and alternating (P)- and (M)-helix molecular arrangements
in the solid state. The peripheral benzyl groups resulted in very
small steric interactions that are responsible for the formation of
columnar stacked arrangements in the crystalline state.
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