Hierarchical supramolecules and organization using boronic acid building blocks

2015 ◽  
Vol 51 (11) ◽  
pp. 2005-2020 ◽  
Author(s):  
Yuji Kubo ◽  
Ryuhei Nishiyabu ◽  
Tony D. James
Keyword(s):  
Smart Materials ◽  
Boronic Acid ◽  
Building Blocks ◽  
Boronic Acids ◽  
Feature Article

Current progress on hierarchical supramolecules using boronic acids has been highlighted in this feature article. The feasibility of the structure-directing ability is fully discussed from the standpoint of the generation of new smart materials.

scholarly journals Two closely related {4-[(N-substituted amino)(diethoxyphosphoryl)methyl]phenyl}boronic acids

2017 ◽  
Vol 73 (1) ◽  
pp. 57-60 ◽  
Author(s):  
Rui Zhang ◽  
Yundi Zhang ◽  
Chunhua Ge ◽  
Jinpeng Miao ◽  
Xiangdong Zhang
Keyword(s):  
Hydrogen Bonds ◽  
Boronic Acid ◽  
Layer Structure ◽  
Building Blocks ◽  
Boronic Acids ◽  
Industrial Chemistry ◽  
Phosphonic Acids ◽  
Multifunctional Compounds ◽  
Phenyl Boronic Acid ◽  
Methyl Phenyl

Organic phosphonic acids and organic phosphonic acid esters have been of much interest due to their applications in the fields of medicine, agriculture and industrial chemistry. Boronic acids can act as synthetic intermediates and building blocks and are used in sensing, protein manipulation, therapeutics, biological labelling and separation. The additional introduction of an aminophosphonic acid group into a boronic acid may give new opportunities for application. To study the structure of such multifunctional compounds, we prepared two new derivatives which can be easily converted to the corresponding phosphonic acids. In the title compounds, {4-[(butylamino)(diethoxyphosphoryl)methyl]phenyl}boronic acid monohydrate, C15H27BNO5P·H2O, (I), and {4-[(diethoxyphosphoryl)(4-nitroanilino)methyl]phenyl}boronic acid, C17H22BN2O7P, (II), three different substituents are attached to a central C—H group, namely 4-boronophenyl, diethoxyphosphoryl and amine. Compound (I) crystallizes as a monohydrate and OB—H...N hydrogen bonds link neighbouring molecules into chains along the [001] direction. The solvent water molecule connects two such chains running in opposite directions. Compound (II) crystallizes as an ansolvate and classical hydrogen bonds result in a layer structure in the (001) plane.

Shape memory alloy–actuated prestressed composites with application to morphing automotive fender skirts

2018 ◽  
Vol 30 (3) ◽  
pp. 479-494 ◽  
Author(s):  
Venkata Siva C Chillara ◽  
Leon M Headings ◽  
Ryohei Tsuruta ◽  
Eiji Itakura ◽  
Umesh Gandhi ◽  
...  
Keyword(s):  
Shape Memory Alloy ◽  
Shape Memory Alloys ◽  
Shape Memory ◽  
Smart Materials ◽  
Design Procedure ◽  
Building Blocks ◽  
Smart Composite ◽  
Thermally Induced ◽  
One Dimensional ◽  
Flat Shape

This work presents smart laminated composites that enable morphing vehicle structures. Morphing panels can be effective for drag reduction, for example, adaptive fender skirts. Mechanical prestress provides tailored curvature in composites without the drawbacks of thermally induced residual stress. When driven by smart materials such as shape memory alloys, mechanically-prestressed composites can serve as building blocks for morphing structures. An analytical energy-based model is presented to calculate the curved shape of a composite as a function of force applied by an embedded actuator. Shape transition is modeled by providing the actuation force as an input to a one-dimensional thermomechanical constitutive model of a shape memory alloy wire. A design procedure, based on the analytical model, is presented for morphing fender skirts comprising radially configured smart composite elements. A half-scale fender skirt for a compact passenger car is designed, fabricated, and tested. The demonstrator has a domed unactuated shape and morphs to a flat shape when actuated using shape memory alloys. Rapid actuation is demonstrated by coupling shape memory alloys with integrated quick-release latches; the latches reduce actuation time by 95%. The demonstrator is 62% lighter than an equivalent dome-shaped steel fender skirt.

scholarly journals A Theoretical Model to Study the Interaction Between Boronic Acids and Insulin

2020 ◽  
Author(s):  
Durgesh Kumar ◽  
Kamlesh Kumari ◽  
PRASHANT SINGH
Keyword(s):  
Amino Acids ◽  
Theoretical Model ◽  
Boronic Acid ◽  
Significant Interaction ◽  
Biological Activities ◽  
Boronic Acids ◽  
Biological Molecules ◽  
Computational Tools ◽  
Medical Expertise ◽  
Stabilizing Agents

Boronic acids are widely used in various applications in view of their ability to recognize and bind at specific sites of the biological molecules to mimic several processes. Therefore, this has attracted the researchers, academician and medical expertise to explore them. In the present work, the authors have designed a theoretical approach to study the interaction of boronic acid with insulin using computational tools. A library of boronic acids (114 compounds) are designed, optimized and interacted with insulin using computational tools i.e. iGEMDOCK. Further, their different biological activities and toxicity are determined. Results indicates the promising potential of the boronic acids on interaction with the insulin. Amongst, 114 molecules of boronic acids, 3-Benzyloxyphenylboronic acid (71) showed the best interaction with amino-acids of insulin and significant interaction was shown with the Glu21 and His5 residues. Further, these results were compared with the stabilizing agents and found to be more potent.

scholarly journals Rapid approach to complex boronic acids

2019 ◽  
Vol 5 (7) ◽  
pp. eaaw4607 ◽  
Author(s):  
Constantinos G. Neochoritis ◽  
Shabnam Shaabani ◽  
Maryam Ahmadianmoghaddam ◽  
Tryfon Zarganes-Tzitzikas ◽  
Li Gao ◽  
...  
Keyword(s):  
Small Molecules ◽  
Boronic Acid ◽  
Multicomponent Reactions ◽  
Chemical Space ◽  
Building Blocks ◽  
Acid Synthesis ◽  
Success Rates ◽  
Boronic Acid Derivatives ◽  
Low Coverage ◽  
Target Synthesis

The compatibility of free boronic acid building blocks in multicomponent reactions to readily create large libraries of diverse and complex small molecules was investigated. Traditionally, boronic acid synthesis is sequential, synthetically demanding, and time-consuming, which leads to high target synthesis times and low coverage of the boronic acid chemical space. We have performed the synthesis of large libraries of boronic acid derivatives based on multiple chemistries and building blocks using acoustic dispensing technology. The synthesis was performed on a nanomole scale with high synthesis success rates. The discovery of a protease inhibitor underscores the usefulness of the approach. Our acoustic dispensing–enabled chemistry paves the way to highly accelerated synthesis and miniaturized reaction scouting, allowing access to unprecedented boronic acid libraries.

scholarly journals Catalytic enantioselective synthesis of α-aryl α-hydrazino esters and amides

2020 ◽  
Vol 56 (43) ◽  
pp. 5823-5826
Author(s):  
Marta Velázquez ◽  
Saúl Alberca ◽  
Javier Iglesias-Sigüenza ◽  
Rosario Fernández ◽  
José M. Lassaletta ◽  
...  
Keyword(s):  
Building Blocks ◽  
Boronic Acids ◽  
Enantioselective Synthesis

Asymmetric 1,2-addition of aryl boronic acids to N-carbamoyl (Cbz and Fmoc) protected glyoxylate-derived hydrazones affords α-aryl α-hydrazino esters/amides, key building blocks en route to artificial peptides.

(DPEPhos)Ni(mesityl)Br: An Air-Stable Pre-Catalyst for Challenging Suzuki–Miyaura Cross-Couplings Leading to Unsymmetrical Biheteroaryls

Synlett ◽  
2018 ◽  
Vol 29 (06) ◽  
pp. 799-804 ◽  
Author(s):  
Mark Stradiotto ◽  
Ryan Sawatzky
Keyword(s):  
Boronic Acid ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Mild Conditions

The successful application of (DPEPhos)Ni(mesityl)Br (C1) as a pre-catalyst in the Suzuki–Miyaura cross-coupling of heteroaryl chlorides or bromides and heteroaryl boronic acids is reported. The use of C1 in this context allows for such reactions to be conducted under mild conditions (2 mol% Ni, 25 °C), including cross-couplings leading to unsymmetrical biheteroaryls. Successful transformations of this type involving problematic pyridinyl boronic acid substrates (10 mol% Ni, 60 °C) are also described.

Pyridynes and indolynes as building blocks for functionalized heterocycles and natural products

2015 ◽  
Vol 51 (1) ◽  
pp. 34-45 ◽  
Author(s):  
Adam E. Goetz ◽  
Tejas K. Shah ◽  
Neil K. Garg
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Feature Article

This feature article showcases the use of pyridynes and indolynes to construct functionalized heterocycles and complex natural products.

scholarly journals Low-Temperature Meltable Elastomers Based on Linear Polydimethylsiloxane Chains Alpha, Omega-Terminated with Mesogenic Groups as Physical Crosslinkers: A Passive Smart Material with Potential as Viscoelastic Coupling. Part I: Synthesis and Phase Behavior

Polymers ◽  
2020 ◽  
Vol 12 (11) ◽  
pp. 2476 ◽  
Author(s):  
Sabina Horodecka ◽  
Adam Strachota ◽  
Beata Mossety-Leszczak ◽  
Beata Strachota ◽  
Miroslav Šlouf ◽  
...  
Keyword(s):  
Low Temperature ◽  
Smart Materials ◽  
Self Assembly ◽  
Lamellar Structure ◽  
Volume Fraction ◽  
Polymer Networks ◽  
Polarized Light ◽  
Building Blocks ◽  
Structure Property ◽  
Mechanical Coupling

Physically crosslinked low-temperature elastomers were prepared based on linear polydimethylsiloxane (PDMS) elastic chains terminated on both ends with mesogenic building blocks (LC) of azobenzene type. They are generally (and also structurally) highly different from the well-studied LC polymer networks (light-sensitive actuators). The LC units also make up only a small volume fraction in our materials and they do not generate elastic energy upon irradiation, but they act as physical crosslinkers with thermotropic properties. Our elastomers lack permanent chemical crosslinks—their structure is fully linear. The aggregation of the relatively rare, small, and spatially separated terminal LC units nevertheless proved to be a considerably strong crosslinking mechanism. The most attractive product displays a rubber plateau extending over 100 °C, melts near 8 °C, and is soluble in organic solvents. The self-assembly (via LC aggregation) of the copolymer molecules leads to a distinctly lamellar structure indicated by X-ray diffraction (XRD). This structure persists also in melt (polarized light microscopy, XRD), where 1–2 thermotropic transitions occur. The interesting effects of the properties of this lamellar structure on viscoelastic and rheological properties in the rubbery and in the melt state are discussed in a follow-up paper (“Part II”). The copolymers might be of interest as passive smart materials, especially as temperature-controlled elastic/viscoelastic mechanical coupling. Our study focuses on the comparison of physical properties and structure–property relationships in three systems with elastic PDMS segments of different length (8.6, 16.3, and 64.4 repeat units).

scholarly journals Carbonylative Suzuki–Miyaura couplings of sterically hindered aryl halides: synthesis of 2-aroylbenzoate derivatives

2020 ◽  
Vol 18 (9) ◽  
pp. 1754-1759 ◽  
Author(s):  
Aya Ismael ◽  
Troels Skrydstrup ◽  
Annette Bayer
Keyword(s):  
Boronic Acid ◽  
Boronic Acids ◽  
Aryl Halides ◽  
Aryl Bromides ◽  
Sterically Hindered

A new protocol for carbonylative coupling of sterically hindered aryl bromides with boronic acids featuring slow addition of the boronic acid as a strategy to suppress unwanted non-carbonylative couplings for sterically hindered aryl bromides.

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