Thiol-ene reactions of 1,3,5-triacryloylhexahydro-1,3,5-triazine (TAT): facile access to functional tripodal thioethers

Rim, Chinwon; Lahey, Lauren J.; Patel, Vijita G.; Zhang, Hongming; Son, David Y.

doi:10.1016/j.tetlet.2008.11.094

Cited by 34 publications

(29 citation statements)

References 51 publications

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“…It could be concluded that the reactivity of MimMP was higher than the previous ones. It may have been related to the existence of imidazolium cation and initiated radicals 32, 35…”

Section: Resultsmentioning

confidence: 99%

“…Interestingly, when the loading of MimMP was higher (>4 phr), the dependence of G ′ on strains did not have a normal pattern similar to others but had first an increased and then a decreased pattern with increasing strains. Because of the high reactivity of the thiol–ene chemistry,32, 37 which could be further activated by quaternary ammonium salt,35 the compound with such a high concentration of MimMP may have been premature at 100°C. Consequently, when MimMP was gradually grafted onto the SBR chains, the value of G ′ initially increased, even with increasing strains.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, the thiol–ene chemistry has been widely focused for its mild reaction conditions, high reactivity, and excellent yielding. This chemistry has been extensively investigated in the technology of photocrosslinking32, 33 and in the fabrication of functional matrials 33–38. In this work, a thiol group was introduced into IL.…”

Section: Introductionmentioning

confidence: 99%

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Thiol‐containing ionic liquid for the modification of styrene–butadiene rubber/silica composites

Lei

Tang

Zhu

et al. 2011

J of Applied Polymer Sci

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To introduce thiol-ene chemistry in the modification of composites by ionic liquid (IL), a novel functional IL, 1-methylimidazolium mercaptopropionate (MimMP), was synthesized and investigated as a modifier for styrene-butadiene rubber/silica composites. MimMP could be hydrogen-bonded with silica and react with the double bonds of rubber chains via thiol-ene chemistry. The filler networking, curing behavior, filler dispersion, crosslink density, and mechanical performance were fully studied. The filler networking in the uncured rubber compounds was effectively restrained. The vulcanization was largely accelerated by MimMP. The interfacial interaction was quantitatively evaluated and found to consistently increase with increasing MimMP. The mechanical performance and abrasion resistance of the modified vulcanizates improved considerably. The remarkable improvements were mainly ascribed to the improved interfacial structure comprised of MimMP-silica hydrogen bonding and MimMP-rubber covalent bonds via thiol-ene chemistry.

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“…It could be concluded that the reactivity of MimMP was higher than the previous ones. It may have been related to the existence of imidazolium cation and initiated radicals 32, 35…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Thiol‐containing ionic liquid for the modification of styrene–butadiene rubber/silica composites

Lei

Tang

Zhu

et al. 2011

J of Applied Polymer Sci

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“…In addition to TBMB, other small-molecule scaffolds such as 1,3,5-triacryoyl-1,3,5-triazinane (TATA), N,N',N”-(benzene-1,3,5-triyl)tris(2-bromoacetamide) (TBAB), and N,N',N”-benzene-1,3,5-triyltrisprop-2-enamide have also been used to generate bicyclic peptides of different ring sizes and flexibility. [35] Alternatively, phage displayed bicyclic peptides can be formed via two disulfide bonds. To prevent the formation of a mixture of different disulfide bridges, Heinis and co-workers designed di-thiol amino acids (DTaas).…”

Section: Synthesis Of Bicyclic Peptidesmentioning

confidence: 99%

Bicyclic Peptides as Next‐Generation Therapeutics

Rhodes

Pei

2017

Chemistry A European J

138

107

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Bicyclic peptides have greater conformational rigidity and metabolic stability than linear and monocyclic peptides and are capable of binding to challenging drug targets with antibody-like affinity and specificity. Powerful combinatorial library technologies have recently been developed to rapidly synthesize and screen large bicyclic peptide libraries for ligands against enzymes, receptors, and protein-protein interaction targets. Bicyclic peptides have been developed as potential therapeutics against a wide range of diseases, drug targeting agents, imaging/diagnostic probes, and research tools. In this minireview, we provide a summary of the recent progresses on the synthesis and applications of bicyclic peptides.

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“…28), 29) For these reasons the thiol-ene reaction has garnered much attention lately as a "click" reaction. 28), 29) Vinyl SQs offer potential use as organicinorganic hybrid monomers for polymerization reactions and/or in the preparation of block copolymers, for example. 24),25),30)36) They can be also used as novel crosslinking agents in polymer systems.…”

Section: Introductionmentioning

confidence: 99%

Facile thiol-ene reactions of vinyl T<sub>10</sub>/T<sub>12</sub> silsesquioxanes for controlled refractive indices for transparent fiber glass reinforced composites

Asuncion

Krug

Abu-Seir

et al. 2015

J. Ceram. Soc. Japan

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A series of thioether-functionalized silsesquioxanes (SQs) was synthesized by radically initiated thiol-ene reactions of vinyl T 10 / T 12 SQ cages with a variety of commercially available thiols. The objectives of this study were to develop model reactions as the basis for using the vinyl T 10/12 compounds as novel crosslinking agents in the synthesis of new types of thiol-ene crosslinked polymers. A second motivation was to develop model compounds with controlled refractive indices and Abbe numbers as possibly modifiers of polymers used for a wide variety of optical and photonic applications. The reactions proceed under mild conditions over 24 h to give thioether SQs in high yields (>90%) and high purity without complex workup. The ease of synthesis coupled with the wide variety and availability of functionalized thiols provides a simple route to elaborating and functionalizing vinyl SQ cages. In addition, the resulting compounds exhibit refractive indices to 1.52 coupled with Abbe numbers to 51 due to the uniquely high electron density provided by the incorporated sulfur atoms, making them ideal compounds for use with optically transparent materials. In addition, cured forms of these compounds provide methods of raising the Abbe number of epoxy resins designed to index match fiberglass with the intent of making transparent fiberglass reinforced composites.

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Thiol-ene reactions of 1,3,5-triacryloylhexahydro-1,3,5-triazine (TAT): facile access to functional tripodal thioethers

Cited by 34 publications

References 51 publications

Thiol‐containing ionic liquid for the modification of styrene–butadiene rubber/silica composites

Thiol‐containing ionic liquid for the modification of styrene–butadiene rubber/silica composites

Bicyclic Peptides as Next‐Generation Therapeutics

Facile thiol-ene reactions of vinyl T<sub>10</sub>/T<sub>12</sub> silsesquioxanes for controlled refractive indices for transparent fiber glass reinforced composites

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