Cyclic tetravinylsiloxanetetraols as hybrid inorganic–organic thiol-ene networks

Sparks, Bradley J.; Kuchera, Timothy; Jungman, Matthew J.; Richardson, Adam D.; Savin, Daniel A.; Hait, Sukhendu; Lichtenhan, Joseph D.; Striegel, Mary F.; Patton, Derek L.

doi:10.1039/c2jm15484f

Cited by 22 publications

(17 citation statements)

References 23 publications

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“…Quite recently, Sparks et al reported the synthesis of cyclic tetravinylsiloxanetetraol [ViSi(OH)O] 4 by acidic hydrolysis of potassium cis-tetravinyltetrasiloxanolate in ethyl acetate [24]. The authors isolated the all-cis isomer and described it as reasonably stable, but the yield was not given.…”

Section: Allcis-[phsi(oh)o] 6 Tris-cis-tris-trans-[phsi(oh)o]mentioning

confidence: 99%

“…Potassium tetravinyltetracyclosiloxanolate was prepared according to the literature procedure [24]. Triethoxyvinylsilane (0.235 mol) and a mixture of anhydrous ethanol (30 ml) and water (0.4 ml) were simultaneously added drop-wise to a mixture of hexanes (220 ml) and KOH (0.276 mol) in a round-bottom flask equipped with a magnetic stirrer and a thermometer.…”

Section: Potassium Tetravinyltetracyclosiloxanolatementioning

confidence: 99%

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Synthesis of Ladder Silsesquioxanes by in situ Polycondensation of Cyclic Tetravinylsiloxanetetraols

Kowalewska

Nowacka

2014

Silicon

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Functionalized tetrahydroxy-cyclotetrasiloxanes are very attractive precursors of tetrasiloxane ring systems in linear silsesquioxanes (LPSQs). Vinyl groups are especially important since they can be employed for various chemical transformations (e.g. hydrosilylation, metathesis reactions, thiol-ene addition). However, isolation of such highly reactive species bearing small side substituents at silicon atoms with high yield is challenging. We overcame the problem by in situ condensation of 2,4,6,8-tetrahydroxy-2,4,6,8-tetravinyl-cyclotetrasiloxanes, derived from potassium organosiloxanolateOligomeric LPSQ materials having a siloxane backbone with ladder structure and functionalized with side vinyl groups were thus prepared. Hexamethyldisilazane was employed for chain termination. The liquid materials show remarkably good solubility in organic solvents. They were isolated and characterized using spectroscopic methods. Information on their structure and molecular masses was derived from MALDI-TOF and MALLS measurements. Size exclusion chromatography (RI detection, volume of elution measurements) was also used. The products were characterized by wide-angle X-Ray diffraction measurements (WAXS) and their thermal characteristics (TGA and DSC) were obtained.

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Section: Allcis-[phsi(oh)o] 6 Tris-cis-tris-trans-[phsi(oh)o]mentioning

confidence: 99%

Section: Potassium Tetravinyltetracyclosiloxanolatementioning

confidence: 99%

Synthesis of Ladder Silsesquioxanes by in situ Polycondensation of Cyclic Tetravinylsiloxanetetraols

Kowalewska

Nowacka

2014

Silicon

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“…The PDMS‐based hybrid organic/inorganic design strategy could overcome the shortcomings of traditional thiol–ene networks derived from flexible sulfide bonds. Thiol–ene‐functionalized organic and inorganic materials can be synergistically combined to improve the properties of a material, for example, rubbery modulus, abrasion resistance, and thermal stability 27. In our previous work we prepared silicone rubber by using thiol–ene “click” chemistry,28 but extensive and diverse research is still needed to extend the thiol–ene reaction to practical applications.…”

Section: Introductionmentioning

confidence: 99%

Polysiloxane‐Based Luminescent Elastomers Prepared by Thiol–ene “Click” Chemistry

Zuo

Xue

et al. 2014

Chemistry A European J

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Side-chain vinyl poly(dimethylsiloxane) has been modified with mercaptopropionic acid, methyl 3-mercaptopropionate, and mercaptosuccinic acid. Coordinative bonding of Eu(III) to the functionalized polysiloxanes was then carried out and crosslinked silicone elastomers were prepared by thiol-ene curing reactions of these composites. All these europium complexes could be cast to form transparent, uniform, thin elastomers with good flexibility and thermal stability. The networks were characterized by FTIR, NMR, UV/Vis, and luminescence spectroscopy as well as by scanning electron microscopy, thermogravimetric analysis, and X-ray photoelectron spectroscopy. The europium elastomer luminophores exhibited intense red light at 617 nm under UV excitation at room temperature due to the (5)D0 →(7)F2 transition in Eu(III) ions. The newly synthesized luminescent materials offer many advantages, including the desired mechanical flexibility. They cannot be dissolved or fused, and so they have potential for use in optical and electronic applications.

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“…[23][24][25] Later this method was used by other research groups too. [26][27][28] In this paper we have generalized data on such objects and describe the synthesis of new stereoregular 8-, 12-and 24-membered functional organocyclosiloxanes with Si-H and Si-Vin functional groups. The presence of functional groups allows utilizing these cycles in various reactions such as hydrosilylation, hydrothiolation, metathesis, Heck reactions and others.…”

Section: Introductionmentioning

confidence: 99%

Convenient Synthesis of New Si-H and Si-Vinyl Functionalized Stereospecific 8-, 12- and 24-Membered Cyclosiloxanes

Анисимов¹,

Kononevich²,

Бузин³

et al. 2016

MHC

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Cyclic tetravinylsiloxanetetraols as hybrid inorganic–organic thiol-ene networks

Cited by 22 publications

References 23 publications

Synthesis of Ladder Silsesquioxanes by in situ Polycondensation of Cyclic Tetravinylsiloxanetetraols

Synthesis of Ladder Silsesquioxanes by in situ Polycondensation of Cyclic Tetravinylsiloxanetetraols

Polysiloxane‐Based Luminescent Elastomers Prepared by Thiol–ene “Click” Chemistry

Convenient Synthesis of New Si-H and Si-Vinyl Functionalized Stereospecific 8-, 12- and 24-Membered Cyclosiloxanes

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