Supramolecular Polymerization and Functions of Isoxazole Ring Monomers

Haino, Takeharu; Hirao, Takehiro

doi:10.1246/cl.200031

Cited by 22 publications

(11 citation statements)

References 167 publications

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“…[85] Our group also reported stacked supramolecular systems. [86] These systems demonstrated that suitably organized 3D structures display unique architectures.…”

Section: Self-assembly By π/π Stacking Interactions (Route B)mentioning

confidence: 99%

Nanographene – A Scaffold of Two‐Dimensional Materials

Sekiya

Haino

2021

The Chemical Record

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Substances can be divided into 0D to 3D species based on the number of repeating units (atom, ion, and molecule) and their arrangements in space (point, linear, layer, and solid). Discrete substances belong to 0D species, polymers are examples of 1D species, and molecular crystals are 3D species. Most of the substances belong to one of these species. On the other hand, those categorized into 2D species wherein the repeating units organize a layer are less explored. 2D species have a surface and edges. The incorporation of these structural features into a molecular design can realize multifunctionalized systems that are difficult to achieve by conventional organic synthesis. The development of 2D species is, therefore, the frontier of organic, inorganic, and polymer chemistry. Nanographenes (NGs) are suitable scaffolds for realizing 2D species due to several factors, such as chemical stability and oxygen-containing functional groups on the surface and on the edge, allowing postsynthetic modifications. Our group has utilized NGs with tens of nanometers in diameters for developing 2D species. Carboxy groups on the edge enable us to install various substituents into NGs, offering NG-based functional materials. These studies demonstrate that the integration of NGs with organic chemistry can widen the scope of their applications other than optical materials that are a main application of NGs. We introduce our recent studies on the development of NG-based functional materials realized by postsynthetic modifications. We hope that this account will contribute to the development of the chemistry of 2D species.

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“…[85] Our group also reported stacked supramolecular systems. [86] These systems demonstrated that suitably organized 3D structures display unique architectures.…”

Section: Self-assembly By π/π Stacking Interactions (Route B)mentioning

confidence: 99%

Nanographene – A Scaffold of Two‐Dimensional Materials

Sekiya

Haino

2021

The Chemical Record

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“…These domains can in principle be utilized for developing functional materials such as supramolecular aggregates. Suitably decorated small aromatic molecules can organize stacked supramolecular aggregates [4–12] . Examples are C 3 ‐symmetric benzene‐1,3,5‐tricarboxamide derivatives [12] and hexa‐ peri ‐benzocoronene derivatives [11] .…”

Section: Figurementioning

confidence: 99%

“…Suitably decorated small aromatic molecules can organize stacked supramolecular aggregates. [4][5][6][7][8][9][10][11][12] Examples are C 3 -symmetric benzene-1,3,5-tricarboxamide derivatives [12] and hexa-peri-benzocoronene derivatives. [11] These species self-assembled to form one-dimensional structures that assembled to organize unique morphologies, such as helical and tubular structures.…”

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confidence: 99%

Self‐Assembly of Nanographenes

2021

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Suitably decorated small aromatic systems can organize stacked structures that display interesting properties arising from their unique morphologies. Although nanographenes produced by top‐down methods have graphitic domains and can in principle be applied for such supramolecular systems, to our knowledge, no such example has been reported thus far. This is partly because of their limited solubility in organic solvents and partly because of their wide lateral size distribution. To realize nanographene‐based supramolecular aggregates, nanographenes carrying alkyl chains with narrow lateral size distributions are employed. We find that the nanographenes undergo self‐assembly and that self‐assembly is regulated by concentration, solvent polarity, temperature, and sonication. Optical measurements and AFM images indicate that stacked structures are possible candidates for aggregates. A molecular mechanics calculation models the interactions in the aggregates. The nanographenes showed concentration‐dependent morphologies on mica, stacked structures at low concentrations and polymer‐like network structures on mica at higher concentrations.

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“…Phenyl isoxazolyl benzene derivatives are flat conjugated molecules that form helical stacked supramolecular assemblies driven by dipole–dipole and π–π stacking interactions. − The helical conformations are observed to be in equilibrium between plus (P) and minus (M) helices. Incorporating chiral moieties into the phenyl isoxazolyl benzenes turned off the racemic equilibrium, resulting in CPL-active one-handed helical assemblies. − In 2016, our group demonstrated that carbazole-cored phenyl isoxazolyl benzene formed stacked supramolecular assemblies in a cooperative fashion .…”

Section: Introductionmentioning

confidence: 99%

Self-Assembling Behavior and Chiroptical Properties of Carbazole-Cored Phenyl Isoxazolyl Benzenes

et al. 2021

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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.

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Supramolecular Polymerization and Functions of Isoxazole Ring Monomers

Cited by 22 publications

References 167 publications

Nanographene – A Scaffold of Two‐Dimensional Materials

Nanographene – A Scaffold of Two‐Dimensional Materials

Self‐Assembly of Nanographenes

Self-Assembling Behavior and Chiroptical Properties of Carbazole-Cored Phenyl Isoxazolyl Benzenes

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