Aromatic Micelles as a New Class of Aqueous Molecular Flasks

Abstract

Micelles are a versatile class of molecular assemblies typically composed of aliphatic molecules with hydrophilic groups. Polyaromatic molecules with hydrophilic groups, on the other hand, usually do not assemble into micellar structures in water but rather form columnar, π-stacked architectures. This Minireview article focuses on the recent development of aqueous micellar nanostructures with multiple oligoarylene rods or polyaromatic panels. The new micelles with spherical polyaromatic shells, which we name "aromatic micelles", serve as functional molecular flasks with superior binding abilities for medium to very large molecules in water.

A Supramolecular Approach to the Preparation of Nanographene Adlayers Using Water‐Soluble Molecular Capsules

“…[17] In contrast, the V-shaped amphiphilic molecule 1 (Scheme 1) forms micellar capsules (1) n in water and solubilizes various water-insoluble compounds.I np articular, p-conjugated planar molecules,s uch as metalloporphyrins,p hthalocyanines,p entacenes,a nd coronenes,h ave been applied for this purpose. [18,19] We report herein water-soluble molecular capsules consisting of V-shaped amphiphilic molecules for the uptake of large PA Hs (i.e., ovalene,c ircobiphenyl, and dicoronylene; Scheme 1). In this study,w ea lso examined the electrochemical behavior of the PA H-containing molecular capsules and prepared highly ordered adlayers of water-insoluble PA Hs on an Au(111) surface by using the prepared molecular-delivery containers.Initially,w eo btained typical scanning tunneling microscopy (STM) images of several PA Ha dlayers that were prepared by immersing an Au(111) substrate into ab enzene solution saturated with the desired PA H. These images were obtained at an open-circuit potential (OCP) of approximately 0.80 Vi n0 .05 m HClO 4 .T he internal structure,m olecular orientation, and packing arrangement could be observed in the high-resolution STM images (Figure 1).Ovalene (2)w as found to form ah ighly ordered adlayer on Au(111) with as emi-hexagonally packed arrangement.…”

“…[17] In contrast, the V-shaped amphiphilic molecule 1 (Scheme 1) forms micellar capsules (1) n in water and solubilizes various water-insoluble compounds.I np articular, p-conjugated planar molecules,s uch as metalloporphyrins,p hthalocyanines,p entacenes,a nd coronenes,h ave been applied for this purpose. [18,19] We report herein water-soluble molecular capsules consisting of V-shaped amphiphilic molecules for the uptake of large PA Hs (i.e., ovalene,c ircobiphenyl, and dicoronylene; Scheme 1). In this study,w ea lso examined the electrochemical behavior of the PA H-containing molecular capsules and prepared highly ordered adlayers of water-insoluble PA Hs on an Au(111) surface by using the prepared molecular-delivery containers.…”

Alkylation‐, Heating‐, and Doping‐Induced Emission Enhancement of a Polyaromatic Tube in the Solid State

“…

Ap olyaromatic tube with as ubnanometer-sized cavity was efficiently prepared on ag ram-scale through the stereo-controlled cyclotrimerization of ad iphenylanthracene derivativea sakey step. [2][3][4] However,m ultiple-step and time-consuming syntheses are often required for the previoust ubes and their gram-scale preparationsa re uncommon (except for e.g.,c yclodextrins, cucurbiturils, pillarenes, and lipid nanotubes). The emission intensity of the solid-state alkyl-substituted tube is remarkablye nhanced upon heating (up to 1.6 times, F F = 31 %) as well as doping with fluorescent dyes (up to 4.2 times, F F = 83 %) throughe fficient energy transfer.

Tubular nanostructures, providing well-definedo ne-dimensional pores, have garnered much attention due to their characteristic functions such as capturing, separating, and transporting abilitiest oward molecules and metal ions.

…”

“…Successful synthesis of molecular and supramolecular tubes has been widely accomplished using covalentl inks [1] and non-covalenti nteractions, respectively. [2][3][4] However,m ultiple-step and time-consuming syntheses are often required for the previoust ubes and their gram-scale preparationsa re uncommon (except for e.g.,c yclodextrins, cucurbiturils, pillarenes, and lipid nanotubes). In addition, tubular( supra)molecules with strong fluorescent properties in solution are quite limited [5][6][7] and those in the solid state have not been reported so far.T he main reason stems from aggregation-caused emission quenching (ACEQ) effects between fluorescentt ubes (Figure 1a,l eft), as found for the solids amples of common polyaromatic compounds (e.g., pyrene and perylene).…”

Side‐Chain‐Directed Dispersion of MoS2 Nanosheets by V‐Shaped Polyaromatic Compounds

“…[1,12] In addition, the V-shaped compound with bulky substituents on the cornerm ight suppress self-stacks through strong p-stacking interactions, in contrast to aplanar polyaromatic dispersant ( Figure 1d). [13] The non-ionic andn on-coordinative side chains [14] werea lso expectedt oa ssist in the stabilization of the dispersed MoS 2 nanocomposites in organics olvents without the change of the crystalline nanostructure. Anthracene-based, new V-shaped dispersant 1a was synthesized in four steps.…”