Excellent performance of aromatic polyguanamines induced by multiple hydrogen bondable tetraazacalix[2]arene[2]-triazine ring in their main chain

Sasaki, Hikaru; Kotaki, T.; Fujimori, Atsuhiro; Tsukamoto, Tadashi; Suzuki, Eiichi; Oishi, Yoshiyuki; Shibasaki, Yuji

doi:10.1039/c9ra09136j

Cited by 15 publications

(10 citation statements)

References 35 publications

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“…The synthetic data and spectra of the compounds used in this study were described in a recently reported paper. 38 The formation of dichlorotetraazacalix [2]arene 2 triazine and the corresponding polymer can be seen in this paper. All compound data, including 1 H, 13 C, mass spectrometry (MS), elemental analysis, etc., including their purity, have been reported.…”

Section: ■ Experimental Sectionmentioning

confidence: 67%

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Polyguanamine Derivative-Based Supramolecular Assemblies with Multiple Hydrogen Bonding and Their Metal-Scavenging Abilities

et al. 2020

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Polyguanamine derivatives having cyclic moieties constituted by two phenyl and two triazine rings have been synthesized, and a supramolecular organization based on their multiple hydrogen-bonding ability was investigated. The obtained polyguanamine derivatives with cyclic moieties were transparent and amorphous in the bulk state and showed excellent mechanical strength emanating from multiple hydrogen bonds, owing to the abundant amino groups present in the structure. These polyguanamine derivatives formed stable monolayers at the air/water interface. The multilayers were transferred using the Langmuir–Blodgett method, and they formed highly periodic layered structures. To evaluate the metal scavenging ability of the cyclic moieties, the metal ions, Cd2+, Nd3+, and Pd2+, were introduced in the subphase. As a result, the cyclic moieties in the polyguanamine derivatives efficiently captured Cd2+, Nd3+, and Pd2+ metal ions. After the metal was captured, the layered structure of each organized film showed higher periodicity because of rearrangement. Moreover, the annular part had a cup-like structure, and the steric size effect of the ring influenced the metal scavenging.

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Section: ■ Experimental Sectionmentioning

confidence: 67%

“…The synthetic data and spectra of the compounds used in this study were described in a recently reported paper . The formation of dichlorotetraazacalix[2]arene triazine and the corresponding polymer can be seen in this paper.…”

Section: Methodsmentioning

confidence: 99%

Polyguanamine Derivative-Based Supramolecular Assemblies with Multiple Hydrogen Bonding and Their Metal-Scavenging Abilities

et al. 2020

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“…PEG ( M n = 4600) end‐capped with NH 2 functions was prepared according to the previous report. [ 24 ] Figures S1 and S2 in the Supporting Information section show scheme of this synthetic protocol and 1 H NMR/GPC data, respectively.…”

Section: Methodsmentioning

confidence: 99%

Spherulitic Characterization and Hierarchical Structural Evaluation of Azacalixarene‐Polyethylene Glycol Copolymers Containing s‐Triazine Rings

Otsuki,

Terui,

Hoshino

et al. 2023

Macro Chemistry & Physics

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This study investigates the solid‐state structure of a copolymer composed of polyethylene glycol (PEG) and azacalixarene, which has two s‐triazine rings and two phenyl rings alternately crosslinked by amino groups. Azacalixarene derivatives containing a low‐molecular‐weight linker moiety and exhibiting an amorphous structure have been synthesized in previous studies; however, in this study, they are crystallized by the substitution of the linker moiety with PEG. The spherulites formed by the corresponding copolymer possess the ability to form higher‐order structures, growing up to a diameter of 1.7 mm depending on the crystallization conditions. The azacalixarene‐PEG copolymer forms negative spherulites via homogeneous nucleation and exhibits a lamellar period at 13.8 nm. The lamellar crystalline part itself is 5.8 nm in thickness; bulky amorphous regions are also observed in the copolymer structure. Reciprocal lattice analysis results reveal that the crystal parts form a packing structure similar to the crystal lattice of PEG. The promotion of spherulite growth is predicted to reflect the characteristics of the corresponding copolymer, which crystallizes while universally containing many amorphous regions.

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“…In this study, three different c‐PGs, each having the characteristic structural moiety which is comprised of two phenyl rings and two triazine rings alternately linked by amino groups and having a varying connecting moiety, are investigated. In the preparation of the c‐PGs [34] used in this study, cyanuric chloride and m ‐Phenylenediamine ( m PDA) were sequentially reacted at a molar ratio of 2 : 1 to synthesize the cyclic moiety as the first step. Then, 4,4’‐Oxydianiline (ODA), 9,9‐Bis(4‐aminophenyl)fluorene (BAFL), and m PDA were each reacted to produce the connecting moiety.…”

Section: Methodsmentioning

confidence: 99%

“…Newly synthesized polyguanamine derivatives having cyclic moieties (c‐PGs), [34] and their monolayer organization on the surface of an aqueous metal buffer demonstrated metal ion extraction from the subphase [35] . In the past 45 years, polyguanamine materials have attracted minimal attention [36] .…”

Section: Introductionmentioning

confidence: 99%

Tracking and Recovery of Metal Desorption from Organized Films of Polyguanamine Derivatives having Cyclic Moieties

et al. 2020

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Metal desorption behavior of polyguanamine derivatives having cyclic moieties (c-PGs), with metal-scavenging abilities, organized into molecular films was investigated, and a recovery technique was realized. Cadmium (a toxic metal), palladium (a precious metal), and neodymium (a rare earth metal) were studied, along with sodium (a cationic metal). A monolayer of c-PGs forming on an aqueous metal solution surface effectively scavenges cations from the subphase owing to the relative basicity of the cyclic moiety. X-ray photoelectron spectroscopy revealed that cadmium and palladium (both divalent cations) were desorbed by simple 30-60 min ultrasonication of their Langmuir-Blodgett multilayers. Conversely, the desorption of neodymium, a trivalent cation, was very slow. Sodium, a monovalent cation, was difficult to collect. Its valence and monolayer condensation on the aqueous sodium buffer were remarkable, indicating that coordinated sodium ions escape during the monolayer condensation.

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Excellent performance of aromatic polyguanamines induced by multiple hydrogen bondable tetraazacalix[2]arene[2]-triazine ring in their main chain

Abstract: Poly(guanamine)s containing tetraazacalix[2]arene[2]triazine ring within the polymer main-chain show outstanding thermal and mechanical properties arisen from the multiple-hydrogen bond.

Cited by 15 publications

References 35 publications

Polyguanamine Derivative-Based Supramolecular Assemblies with Multiple Hydrogen Bonding and Their Metal-Scavenging Abilities

Polyguanamine Derivative-Based Supramolecular Assemblies with Multiple Hydrogen Bonding and Their Metal-Scavenging Abilities

Spherulitic Characterization and Hierarchical Structural Evaluation of Azacalixarene‐Polyethylene Glycol Copolymers Containing s‐Triazine Rings

Tracking and Recovery of Metal Desorption from Organized Films of Polyguanamine Derivatives having Cyclic Moieties

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