Synthesis of sugar-containing polymers by self-condensation with diboronic acid

Mikami, Masafumi; Shinkai, Seiji

doi:10.1039/c39950000153

Cited by 32 publications

(16 citation statements)

References 6 publications

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“…Again, the long B-N bond correlates with a low tetrahedral character of 69.5 %. The solid-state 11 B NMR spectra of polymers 1, 2, and 4 are in agreement with the depicted structures and show peaks around 10 ppm. An interesting difference was observed when we attempted to make a polymer from methyl boronic acid, 4,4Ј-bipyridine, and 1,2,4,5-tetrahydroxybenzene.…”

Section: Resultssupporting

confidence: 76%

“…An interesting difference was observed when we attempted to make a polymer from methyl boronic acid, 4,4Ј-bipyridine, and 1,2,4,5-tetrahydroxybenzene. Again, a dark-purple precipitate was formed (5), but its solid-state 11 B NMR spectrum showed two peaks at ca. 32 and ca.…”

Section: Resultsmentioning

confidence: 99%

“…[10] An interesting feature of these polymers is that hydrolytic degradation can be reversed by annealing under vacuum ("self-repairing polymers"). [8] The polycondensation of diboronic acids with sugar derivatives as linkers has been investigated by the groups of Shinkai [11] and Shimizu. [12] Again it was found that the polymerization is a reversible process, which depends on the conditions.…”

Section: Introductionmentioning

confidence: 99%

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Formation of Boronate Ester Polymers with Efficient Intrastrand Charge‐Transfer Transitions by Three‐Component Reactions

et al. 2007

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The three-component reaction of aryl boronic acids with 1,2,4,5-tetrahydroxybenzene and 1,2-bis(4-pyridyl)ethylene or 4,4Ј-bipyridine leads to the formation of dark-purple boronate ester polymers. Crystallographic analyses show that the polymer strands have a zig-zag geometry, and the bis(dioxaborole) units are connected by dipyridyl linkers through dative B-N interactions. Upon dissolution of the polymers in hot chloroform, most of the B-N connections are

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Section: Resultssupporting

confidence: 76%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Formation of Boronate Ester Polymers with Efficient Intrastrand Charge‐Transfer Transitions by Three‐Component Reactions

et al. 2007

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“…[81][82][83] Mikami and Shinkai first achieved the synthesis of main-chain sugar-containing polymers through self-condensation with diboronic acid under nonaqueous conditions. 84,85 Based on our continued interest in sugar-based bolaamphiphiles, we have newly synthesized glucuronamideappended bolaamphiphiles 6(n) possessing free 1,2-diols available for ester formation with a bola-form aromatic boronic acid derivative. In order to confirm linear complex formation between the glucuronamideand boronic acid-appended bola-form derivatives, we employed 11 B NMR spectroscopy since it is very sensitive to the spin state of the boron atom, such as neutral sp 2 , anionic sp 3 , and coordinated sp 3 states.…”

Section: Ph-dependent Reversible Polymer Formation From Bola-form Dermentioning

confidence: 99%

Bottom-Up Synthesis and Morphological Control of High-Axial-Ratio Nanostructures through Molecular Self-Assembly

Shimizu

2003

Polym J

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ABSTRACT:Based on our recent results, the present paper overviews noncovalent formation of high-axial-ratio nanostructures (HARNs), such as fibers, rods, tubes and ropes, through molecular self-assembly of bola-form amphiphilic (bolaamphiphilic) monomers. A variety of bolaamphiphiles, in which sugars, peptides, or nucleobases as headgroups are connected to both ends of a hydrocarbon spacer, were newly designed and synthesized. Their self-assembling behavior was examined in aqueous solutions in terms of bottom-up fabrication of organic nanostructures. The morphologies proved to strongly depend on the headgroup structure, spacer chain lengths and even-odd carbon numbers of used oligo(methylene) spacers. Typical examples of self-assembled morphologies include nanofibers from 1-glucosamide-or thymidine-appended bolaamphiphiles, vesicle-encapsulated microtubes from glycylglycine-appended bolaamphiphiles, double-helical ropes from thymine-appended bolaamphiphiles. These self-assembled HARNs are constructed hierarchically in a manner similar to biological structures. On the basis of several solid-state analyses, molecular packing and orientation within the HARNs are discussed and compared with the single crystal structures in terms of hydrogen-bond networks. Furthermore, pH-dependent reversible polymer formation was achieved using the combination of glucuronamideand aromatic boronic acid-appended bola-form derivatives. Polymerization of bola-form 1-glucosamide derivatives with a 1,4-butadiyne group was performed in self-assembled nanometer-sized fibers, giving a single polydiacetylene chain of 64-mer that can be seen in TEM.KEY WORDS High-Axial-Ratio Nanostructure (HARN) / Bolaamphiphile / Self-Assembly / Noncovalent Synthesis / Hydrogen Bond / Nanofiber / Microtube / Nano-Rod / Rope / Hydrogel / Crystal Structure / Biomaterials possess highly organized non-covalent structures formed spontaneously in bottom-up fashion, 1 shaping natural body and functioning as energyconverting and information-converting materials. In contrast, conventional polymers are so-called linear macromolecules in which tens of thousands to millions of low-molecular-weight monomer units are connected to each other through covalent bonds. Very recently, a new family of polymers, including topologically complex polymers 2-13, 18-25 and self-assembled nanostructures, [14][15][16][17]26 has attracted much attention. 27,28 In particular, Kunitake and his co-worker built up the fundamental concept behind the polymolecular materials based on bilayer-containing molecular assemblies. 29,30 Stupp et al., 31, 32 Percec et al., 33 and Whitesides et al. 34,35 also succeeded in a molecule-up fabrication using polymer building blocks to realize nanometersized assemblies with well-defined shapes. The advantage of non-covalent self-assembly technique, unlike chemical reaction or polymerization, is in that it can directly produce ordered two-and three-dimensional structures like sheets, rods, fibers, tubes, disks, and spheres. It is more important that nanostruct...

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“…First to report a linear boronic acid‐derived condensation polymer were Mikami and Shinkai, who reported in 1995 how the reaction between bifunctional aromatic boronic acids and saccharides yielded polymers, as evidenced by circular dichroism (CD) spectroscopy . In their work the boronic acid reacts both with the 1,2‐diol and the 3,4‐ or 4,6‐diol, i.e.…”

Section: Boronate Estermentioning

confidence: 99%

Dynamic covalent polymers

García

Smulders²

2016

J. Polym. Sci. Part A: Polym. Chem.

171

159

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This Highlight presents an overview of the rapidly growing field of dynamic covalent polymers. This class of polymers combines intrinsic reversibility with the robustness of covalent bonds, thus enabling formation of mechanically stable, polymer‐based materials that are responsive to external stimuli. It will be discussed how the inherent dynamic nature of the dynamic covalent bonds on the molecular level can be translated to the macroscopic level of the polymer, giving access to a range of applications, such as stimuli‐responsive or self‐healing materials. A primary distinction will be made based on the type of dynamic covalent bond employed, while a secondary distinction will be based on the consideration whether the dynamic covalent bond is used in the main chain of the polymer or whether it is used to allow side chain modification of the polymer. Emphasis will be on the chemistry of the dynamic covalent bonds present in the polymer, in particular in relation to how the specific (dynamic) features of the bond impart functionality to the polymer material, and to the conditions under which this dynamic behavior is manifested. © 2016 The Authors. Journal of Polymer Science Part A: Polymer Chemistry Published by Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 3551–3577.

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Synthesis of sugar-containing polymers by self-condensation with diboronic acid

Cited by 32 publications

References 6 publications

Formation of Boronate Ester Polymers with Efficient Intrastrand Charge‐Transfer Transitions by Three‐Component Reactions

Formation of Boronate Ester Polymers with Efficient Intrastrand Charge‐Transfer Transitions by Three‐Component Reactions

Bottom-Up Synthesis and Morphological Control of High-Axial-Ratio Nanostructures through Molecular Self-Assembly

Dynamic covalent polymers

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