Ring shape-dependent self-sorting of pillar[n]arenes assembled on a surface

Abstract

Self-sorting, in which multiple components selectively assemble themselves by recognising self from others, is an attractive approach to produce supramolecular assemblies with controlled structures. Lock-and-key type complementary physical interactions are required for self-sorting because selective affinity is necessary to distinguish self from others. Here we show self-sorting behaviour based on a principle of geometrical complementarity by shape during our investigation of assembly of pentagonal pillar[5]arenes and hexagonal pillar[6] arenes on a surface. In the homoassembly systems, anionic pillar[5]arenes and pillar[6]arenes are adsorbed onto positively charged layers of cationic pillar[5]arenes and pillar[6]arenes, respectively, through cationic-anionic electrostatic interactions. In contrast, ionic pillar[5] arenes are adsorbed onto layers constructed from oppositely charged pillar[5]arenes, but ionic pillar[6]arenes are not. Equally, for the reverse combination, ionic pillar[6]arenes are adsorbed onto layers constructed from oppositely charged pillar[6]arenes, but ionic pillar[5] arenes are not. The geometrical complementarity by shape realises effective self-sorting even in non-directional multivalent ionic interactions.

Supramolecular exfoliation of layer silicate clay by novel cationic pillar[5]arene intercalants

“…3 d). In addition, compared to UM, the highly symmetric structure of the pillar[5]arene works to effectively modify clay because it can easily aggregate 28 – 31 .

Figure 3 Effect of chain length and cyclic structure on clay modification.

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Pillararene-Containing Polymers with Tunable Conductivity Based on Host–Guest Complexations

“…For instance, Ogoshi reported self-sorting behavior based on the assembly of pentagonal pillar [5]arenes and hexagonal pillar [6]arenes on a surface. 12 Huang reported a pillar [6]arene-based supramolecular amphiphile, which could respond to dual redox stimuli. 13 However, most of this research focused mainly on the discrete pillararene monomers.…”

“…On the other hand, pillararenes, a new family of macrocyclic hosts, have attracted increasing attention due to their novel symmetries and particularly facile functionalization. For instance, Ogoshi reported self-sorting behavior based on the assembly of pentagonal pillar[5]­arenes and hexagonal pillar[6]­arenes on a surface . Huang reported a pillar[6]­arene-based supramolecular amphiphile, which could respond to dual redox stimuli .…”

Fullerene-containing pillar[n]arene hybrid composites

“…As a significant rising star in macrocycle chemistry, [1][2][3][4][5][6][7][8] the short rigid cylindrical structure of pillar[n]arenes (Scheme 1) 9,10 resembles the molecular architecture of carbon nanotubes, [11][12][13] and provides the possibility of introducing unique planar chirality [14][15][16] by functionalizing larger alkyl and aromatic groups. [17][18][19] In fact, pillar[n]arene could perform as an efficient structural basis for the synthesis of one-dimensional (1D) linear tubular structures, [20][21][22][23][24] and serve as an interesting additive for improving the physiochemical properties of another significant two-dimensional (2D) carbon material, graphene, [25][26][27] for example, to diversify applications in biomedicine and electrochemical sensor devices.…”