Hexagonal shape-persistent macrocycles (SPMs) consisting of three pyridine and three phenol rings linked with acetylene bonds were developed as a preorganized host for saccharide recognition by push-pull-type hydrogen bonding. Three tert-butyl or 2,4,6-triisopropylphenyl substituents were introduced on the host to suppress self-aggregation by steric hindrance. In spite of the simple architecture, association constants Ka of the host with alkyl glycoside guests reached the order of 106  m-1 on the basis of UV/Vis titration experiments. This glycoside recognition was much stronger than that in the cases of acyclic equivalent hosts because of the entropic advantage brought by preorganization of the hydrogen-bonding sites. Solid-liquid extraction and liquid-liquid transport through a liquid membrane were demonstrated by using native saccharides, and much preference to mannose was observed.

D3h -Symmetrical Shape-Persistent Macrocycles Consisting of Pyridine-Acetylene-Phenol Conjugates as an Efficient Host Architecture for Saccharide Recognition.

Discrete Molecular Recognition Induced Higher-Order Structures: Fibrous Formation Triggered by Melamine Recognition with a Cationic Ethynylpyridine Macrocyclic Host.

Tunable luminescence of cyclometallated platinum(II) derivatives based on novel pyrimidine-contained tridentate Pt(NˆCˆN)Cl complexes

Rod-coil molecules 1a, 1b and 2a, 2b, consisting of biphenyl and phenyl units connected by an acetylene bond as the rod segment and oligo(ethylene glycol) (OEG) as the coil segment, were synthesized and characterized. Molecules 1a and 1b incorporate a butoxy group at the apex of their bent-shaped rigid building blocks, while both 1b and 2b contain a lateral methyl group between the rod and coil segments. The self-assembling behavior of these molecules was investigated using DSC, SAXS, CD, AFM, and TEM in bulk and aqueous solutions. In the bulk state, 1a self-assembles into oblique columnar structures, whereas 1b, incorporating butoxy and lateral methyl groups, self-assembles into three-dimensional body-centered tetragonal structures. Molecules 2a and 2b with no butoxy groups, and 2b incorporating a lateral methyl group, self-assemble into hexagonal perforated lamellar and oblique columnar structures, respectively. In dilute aqueous solutions, 1a assembles into tubular nanoassemblies, while 1b self-organizes into micelles and nanoparticles. On the other hand, 2a and 2b spontaneously aggregate into nanoribbons and nanofibers. Furthermore, CD experiments together with AFM investigations of 2b indicate the creation of self-organized helical fibers, implying that the lateral methyl group induces the helical stacking of the rod building block. These results reveal that the butoxy and lateral methyl groups between the rod and coil segments dramatically influence the creation of supramolecular nanostructures and morphologies.

Control of supramolecular nanoassemblies by tuning the interactions of bent-shaped rod-coil molecules.

A macrocycle consisting of six ethynylphenol units was developed as a host architecture for saccharides. The rigid framework of the macrocycle suppressed the intramolecular hydrogen-bonding between adjacent phenolic hydroxy groups and recognized saccharides by intermolecular hydrogen-bonding within the hole. The well-defined hydrogen-bonding sites enabled the size-selective guest recognition and showed preference to pentoses over hexoses.

Preferential Recognition and Extraction to Pentoses over Hexoses by a D6h-Symmetrical Ethynylphenol Macrocycle with Six Inner Phenolic Hydroxy Groups

Study of artificial tubular assemblies as a useful host scaffold for size-selective recognition and release of guest molecules is an important subject in host–guest chemistry. We describe well-defined self-assembled nanotubes (NT6mer) formed from π-conjugated m-phenylene–pyrimidinylene alternated macrocycle 16mer that exhibit size-selective recognition toward a specific aromatic acid. In a series of guest molecules, a size-matched trimesic acid (G3) gives inclusion complexes (NT6mer⊃G3) in dichloromethane resulting in an enhanced and red-shifted fluorescence. 1H nuclear magnetic resonance (NMR) titration experiments indicated that the complex was formed in a 1:1 molar ratio. Density functional theory (DFT) calculations and the binding constant value (K = 1.499 × 105 M–1) of NT6mer with G3 suggested that the complex involved triple hydrogen-bonding interactions. The encapsulated guest G3 molecules can be readily released from the tubular channel through the dissociation of hydrogen bonding by the addition ...

Size-Selective Recognition by a Tubular Assembly of Phenylene–Pyrimidinylene Alternated Macrocycle through Hydrogen-Bonding Interactions

The invention relates to a pyrimidine group-containing rigid conjugated macrocyclic compound, and a preparation method and application thereof, wherein the structural general formula of the compound is shown in the specification, wherein R is one or more independently selected from self-hydrophobic long-chain group, hydrophilic long-chain group, chiral long-chain group, ester group, cyano-group, amino-group, aryl and sulfydryl. The preparation method comprises the following steps of: (1) synthesizing a monomer II; (2) synthesizing a monomer III from the monomer II and 5-bromo-2 iodopyrimidine through Suzuki coupled reaction; and (3) synthesizing the pyrimidine group-containing rigid conjugated macrocyclic compound from the monomer II and the monomer III by a Suzuki coupling one-step cyclization method. The pyrimidine group-containing rigid conjugated macrocyclic compound provided by the invention can be applied to novel functional material development as excellent self-assembly unit molecules; and the pyrimidine group-containing rigid conjugated macrocyclic compound shows special photoelectric properties through coordination with metals with own N heteroatoms, and further can be applied to composite material research.

Pyrimidine group-containing rigid conjugated macrocyclic compound, as well as preparation method and application thereof

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Size-Selective Recognition by a Tubular Assembly of Phenylene–Pyrimidinylene Alternated Macrocycle through Hydrogen-Bonding Interactions

Pyrimidine group-containing rigid conjugated macrocyclic compound, as well as preparation method and application thereof