Simple, low-cost synthetic route to potentially polymerizable silatranes

Cheng, Hengqin; Laine, Richard M.

doi:10.1039/a908291c

Cited by 17 publications

(11 citation statements)

References 17 publications

(5 reference statements)

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“…15 This latter work has been followed up by extensive efforts by Lewis et al demonstrating that a number of silica sources can be used and that, in some instances, methylsilanes can also be produced. 16 We have also explored silica dissolution using the saturated analog of catechol, ethylene glycol (egH 2 ), giving quantitative yields of new glycolatosilicates, [17][18][19][20] 19 Dissolution thermodynamics are similar to those found for pressurized SiO 2 dissolution in aqueous base at similar temperatures, used commercially to make silicates. 21,22 For Scheme 5(a-c), where the products are neutral alkoxysilanes, the activation energies are similar, 19…”

Section: Introductionmentioning

confidence: 87%

The selective dissolution of rice hull ash to form [OSiO1.5]8[R4N]8(R = Me, CH2CH2OH) octasilicates. Basic nanobuilding blocks and possible models of intermediates formed during biosilicification processes

et al. 2005

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Section: Introductionmentioning

confidence: 87%

The selective dissolution of rice hull ash to form [OSiO1.5]8[R4N]8(R = Me, CH2CH2OH) octasilicates. Basic nanobuilding blocks and possible models of intermediates formed during biosilicification processes

et al. 2005

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“…There have been some other examples to date explicitly targeting various silatranes having N-(het)oxamethylpropyl 58 (het = 1-hydroxymethyl-3,5-dimethylpyrazole, 1-hydroxymethylbenzotriazole, 1-hydroxymethylimidazole) as X group. With an intention to study Diels-Alder or cross coupling reaction of silatranes, Welkar et al 59,60 reported a simple and convenient route to synthesize (buta-1,3-dien-2-yl)silatrane (78). Several additional silatranes having C 5 H 5 61 and 2-ethoxycarbonylvinyl 62 (79) as X substituent, containing metals such as Te and Se (80-84), 63 N,N 0 -bis(3-silatranylpropyl)malonicdiamide and pthalicdiamide (85 and 86) 64 and 1,1-dimethyl-1-(silatranylmethyl)hydrazinium (87 and 88) halides 65 were also obtained by addition of triethanolamine to the corresponding silane.…”

Section: Varinder Kaur Chahalmentioning

confidence: 99%

“…77 In another approach, kilogram quantities of 2-silatranyloxy-1-ethanol (121) were obtained in one step. 78…”

Section: Varinder Kaur Chahalmentioning

confidence: 99%

“…This derivative undergoes facile ligand exchange allowing the synthesis of a number of reactive compounds which are useful for producing silatrane-containing polymers as shown in Scheme 25. 78 In a similar way, alkoxy-and acetoxysilatranes have been synthesized by alkoxide exchange of silatranes (obtained from silica) in acidic alcohols and acetic anhydride, respectively. 76 1-Acyloxysilatranes can be synthesized efficiently by exchange reaction between 1-ethoxysilatrane and the corresponding acyl iodide (acetyl and benzoyl).…”

Section: Exchange Reactionsmentioning

confidence: 99%

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Silatranes: a review on their synthesis, structure, reactivity and applications

2011

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This critical review summarizes progress of the rapidly developing and very active field of silatrane chemistry. The first part of the review deals with general synthetic approaches used to synthesize different silatranes. The most interesting feature of silatranes, i.e., variation of Si-N bond length on the basis of the axial substituent of Si, and other structural features, are described in the second part with special emphasis on crystallographic and theoretical studies. It is followed by a discussion on the reactivity of various silatranes. Silatranes have now gained acceptance for a wide variety of applications which are summarized in the last section of review. Some of them have extensive interest due to their medical use to heal wounds or stimulate hair-growth (pilotropic activity), biological properties, pharmacological properties e.g. antitumor, anticancer, antibacterial, anti-inflammatory, fungicidal activity, stimulating effect in animal production and seed germination effects. The review focuses on the extended potential of silatranes in sol-gel processes, mesoporous zeotypes, atomic force microscopy, commercial products such as adhesion promoters, polymer formation and rubber compositions. This critical review will be helpful for general researchers, experts, advanced undergraduates and newcomers working on silatrane chemistry as this review presents greater emphasis on synthesis and characterization, structural properties, reactivity and applications of silatranes in the field of biology, material science, sol-gel chemistry, pharmaceutics, agriculture and medicine (311 references).

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“…The structure of the polymerizable methacryloylsilatrane (MPS) examined in this paper is shown in Scheme . It is to be noted that the use of several polymerizable silatranes, including MPS, has been proposed so far . However, the characterization and physicochemical properties of these polymers have not been reported adequately.…”

Section: Introductionmentioning

confidence: 99%

Preparation and utilization of poly(methacryloylsilatrane) as a salt‐dissociation enhancer in PEO‐based polymer electrolytes

Mizumo

Kajihara

Yamada

et al. 2013

Polymers for Advanced Techs

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Polymers containing silatrane units were prepared by the free radical polymerization of methacryloylsilatrane (MPS), and their conductivities were evaluated. We confirmed that MPS can be polymerized without excessive decomposition of the silatrane units by the radical polymerization initiated by azobisisobutyronitrile. The chemical structure of the polymerized MPS (pMPS) was characterized by Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, gel permeation chromatography, and matrix‐assisted laser desorption/ionization time‐of‐flight mass spectroscopy. The pMPS formed a homogeneous complex with lithium trifluoromethyl sulfonate (LiOTf), although the obtained pMPS/LiOTf complex did not show conductivity. The negligible conductivity was caused by the high glass transition temperature (Tg) of the pMPS matrix, which exceeded 70°C. The pMPS was subsequently utilized as a salt‐dissociation enhancer for the poly(ethylene oxide)‐based polymer electrolyte. MPS was copolymerized with poly[methacryloyl oligo(ethylene oxide)] (pMEO) by free radical polymerization. When the pMEO incorporated a small amount of MPS units (i.e. lower than 15 mol%), the elevation in Tg was not observed, and the conductivity markedly improved. Among the series of copolymers and when compared with pristine pMEO, the copolymer containing 6.3% of MPS units had the maximum conductivity (3.1 × 10−4 S cm−1 at 80°C). The Vogel–Fulcher–Tammann fitting parameters showed that the conductivity was improved by the increase in the number of carrier ions. The enhancement in salt dissociation was presumably due to the homogeneous incorporation of polar MPS units. However, when the MPS unit content exceeded 15 mol%, the conductivity was lowered because of the increase in Tg. Copyright © 2013 John Wiley & Sons, Ltd.

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Simple, low-cost synthetic route to potentially polymerizable silatranes

Cited by 17 publications

References 17 publications

The selective dissolution of rice hull ash to form [OSiO1.5]8[R4N]8(R = Me, CH2CH2OH) octasilicates. Basic nanobuilding blocks and possible models of intermediates formed during biosilicification processes

The selective dissolution of rice hull ash to form [OSiO1.5]8[R4N]8(R = Me, CH2CH2OH) octasilicates. Basic nanobuilding blocks and possible models of intermediates formed during biosilicification processes

Silatranes: a review on their synthesis, structure, reactivity and applications

Preparation and utilization of poly(methacryloylsilatrane) as a salt‐dissociation enhancer in PEO‐based polymer electrolytes

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