22235-02-5

Upstream product

• 80-05-7 BPA 
• 106-96-7 propargyl bromide 
• 7705-08-0 iron(III) chloride 
• 624-65-7 2-propynyl chloride 

Relevant academic research and scientific papers

Exploring thiol-yne based monomers as low cytotoxic building blocks for radical photopolymerization

The last decade has seen a remarkable interest in the development of biocompatible monomers for the realization of patient specific medical devices by means of UV-based additive manufacturing technologies. This contribution deals with the synthesis and investigation of novel thiol-yne based monomers with a focus on their biocompatibility and also the mechanical properties in their cured state. It could be successfully shown that propargyl and but-1-yne-4-yl ether derivatives have a significant lower cytotoxicity than the corresponding (meth)acrylates with similar backbones. Together with appropriate thiol monomers, these compounds show reactivities in the range of (meth)acrylates and almost quantitative triple bond conversions. A particular highlight is the investigation of the network properties of photo cured alkynyl ether/thiol resins by means of low field solid state nuclear magnetic resonance spectroscopy. Additionally, dynamic mechanical analysis of those polymers revealed that monomers containing rigid backbones lead to moduli and glass transition temperatures (Tg's), sufficiently high for the fabrication of medical devices by UV based additive manufacturing methods.

Synthesis, optical properties, and antioxidant and anticancer activity of benzoheterazole dendrimers with triazole bridging unit

Triazole-bridged benzoheterazole dendrimers with a bisphenol/benzophenone core unit have been synthesized by click chemistry via a convergent approach. The optical properties of the benzoheterazole dendrimers and their modulation under the influence of the dendritic environment are investigated. All the synthesized benzoheterazole dendrimers show antioxidant properties comparable to those of the standards, viz: gallic acid and ascorbic acid, when tested by DPPH and ABTS radical scavenging methods. Higher generation dendrimers exhibit superior antioxidant activity than the lower generation dendrimers due to the presence of a higher number of 1,2,3-triazole and benzophenone units. The therapeutic efficacy of the benzoheterazole dendrimers in inhibiting the growth of the A549 cancer cell increases as the dendritic generation increases. Our study shows that the inhibition of cell proliferation is dose and time dependent. MTT assay, cell viability, cell counting, and clonogenic assay indicate that the benzoheterazole dendrimers inhibit the growth of cancer cells, as revealed by reactive oxygen species and mitochondrial membrane potential studies. Morphological changes of the cancer cell line after treatment with the benzoheterazole dendrimers showed the typical features of cell death cell shrinkage and reduction in the number of cancer cells.

Thermally curable acetylene-containing main-chain benzoxazine polymers via sonogashira coupling reaction

Propargyl containing thermally curable benzoxazine precursors in the main chain have been synthesized from iodo functional bisbenzoxazine and diacetylenes by Sonogashira coupling reaction. For this purpose, 4,4′- isopropylidenediphenol (Bisphenol A) was reacted with formaldehyde and iodoaniline to form diiodobisbenzoxazine (DIBB). Sonogashira coupling reaction between DIBB and diacetylene bisether (DABE) or diacetylene bisbenzoxazine (DABB) catalyzed by palladium tetrakistriphenylphosphine yields the corresponding main-chain polybenzoxazine precursors with the molecular weights around 2300-3500 Da. The structures of the monomers and the resulting polymers are confirmed by FT-IR and 1H NMR spectral analysis. Curing behaviors of both the monomer and polymers were studied by differential scanning calorimetry (DSC). Thermal properties of the cured polymers were also investigated by thermogravimetric analysis (TGA).

Rapid, Photomediated Healing of Hexaarylbiimidazole-Based Covalently Cross-Linked Gels

The intrinsic healing of covalently cross-linked polymer networks is commonly effected via the utilization of backbone-borne functional groups able to reversibly cleave or rearrange, thereby enabling mixing and coreaction of network strands that bridge co

Dipropargyl ether bisphenol A based boron-containing polymer: Synthesis, characterization and molecular dynamics simulations of the resulting pyrolysis and carbonization

Boron-containing polymers have recently attracted worldwide attention due to their ability to affect the thermal and oxidation resistance of an in situ formed material during pyrolytic carbonization. In this work, a novel dipropargyl ether bisphenol A based boron-containing (PB) precursor polymer, which can thermally cure via propargyl groups, was synthesized. PB was characterized with Fourier transform infrared spectroscopy and nuclear magnetic resonance (1H, 11B and 13C). Thermogravimetric analysis indicated the outstanding thermo-oxidative stability of PB thermosets with the temperature of 5% weight loss of 362 °C and char yield of 56.7% at 800 °C in air, while those are 416 °C and 74.0%, respectively, in nitrogen. The time evolution of major pyrolysis products including pyrolysis mechanism of PB thermosets were examined via thermogravimetry-Fourier transform infrared spectra as well as reactive molecular dynamics (ReaxFF-MD) simulations. In addition, the carbonized structure of PB thermosets was analyzed using X-ray photoelectron spectroscopy and X-ray powder diffraction. Formation of the graphitic fragment was simulated with ReaxFF-MD. Combining the ReaxFF-MD simulation with the experimental analysis, the way that boron atoms insert into the graphitic structure was illustrated.

Synthesis, characterization and evaluation of optical band gap of new semiconductor polymers with N-aryl- 2,5-diphenyl-pyrrole units

We used chemical modification to obtain new polymers that contain pyrrole units in the main chain, with electron-withdrawing groups acting as potential organic semiconductors, by means of chemical modification of the diacetylene-containing precursors. The

Ultrasound Promoted Step-Growth Polymerization and Polymer Crosslinking Via Copper Catalyzed Azide–Alkyne “Click” Reaction

Mechano-activated chemistry is a powerful tool for remodeling of synthetic polymeric materials, however, few reactions are currently available. Here we show that using piezochemical reduction of a CuII-based pre-catalyst, a step-growth polymerization occurs via the copper catalyzed azide–alkyne cycloaddition (CuAAC) reaction to form a linear polytriazole. Furthermore, we show that a linear polymer can be crosslinked mechanochemically using the same chemistry to form a solid organogel. We envision that this chemistry can be used to harness mechanical energy for constructive purposes in polymeric materials.

Mechanistic and kinetic aspects of the curing of phthalonitrile monomers in the presence of propargyl groups

The influence of propargyl groups on the thermal polymerization of phthalonitrile groups has been examined through reaction of a blend of a bisphthalonitrile viz. 2,2-bis(4-phthalonitrile oxy phenyl)propane and a bispropargyl ether viz. 2,2-bis(4-proparyloxy phenyl)propane (BPhPR). The possibilities for co-reaction of the propargyl and phthalonitrile moieties and/or the catalytic nature of the cure reaction prevailing in their blends were indicated by multiple exotherms in differential scanning calorimetry and dynamic rheological experiments. These have been attributed to homopolymerization of propargyl, hydroxyl and chromene mediated nitrile polymerization. FT-IR and fluorescence emission spectroscopic investigations on model compounds confirmed that nitrile polymerization was favoured by the chromene and hydroxyl groups formed by Claisen rearrangement. Activation energy of the reaction step involving chromene mediated phthalonitrile crosslinking was found to be 89 kJ/mol which was close to the value of phenol catalysed phthalonitrile curing.

A convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation

A highly convenient method has been developed for the synthesis of (prop-2-ynyloxy) benzene and its derivatives. Differently substituted phenol and aniline derivatives were allowed to react with propargyl bromide in the presence of K2CO3/

One-pot synthesis of precise polyisoxazoles by click polymerization: Copper (I)-catalyzed 1,3-dipolar cycloaddition of nitrile oxides with alkynes

This article reports a new one-pot method for polymer preparation, which involves double click chemistry. In one pot, two click reactions take place sequentially by adding the reactants step by step. The first click reaction is to produce the monomer for