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ÇAKMAKÇI, EMRAH

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ÇAKMAKÇI

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    DOPO tethered Diels Alder clickable reactive silica nanoparticles for bismaleimide containing flame retardant thiol-ene nanocomposite coatings
    (ELSEVIER SCI LTD, 2017) OKTAY, BURCU; Oktay, Burcu; Cakmakci, Emrah
    The modification of nanoparticles (NPs) with functional groups that render them much more compatible with the polymeric matrices to prepare organic-inorganic hybrid materials is an active area of research. In this work, flame retardant and reactive nanosilica particles were prepared. First, nanosilica particles were coated with aminosilane and then reacted with furfural to introduce Diels Alder clickable sites. Finally, these reactive NPs were phosphorylated by reacting them with 9,10-dihydro-9-oxy-10-phosphaphenanthrene-10-oxide (DOPO). Different amounts of DOPO tethered Diels Alder clickable nanosilica particles (DDAS) were added to a bismaleimide resin containing thiol-ene based liquid pho-tocurable mixture. Bismaleimide acted as a crosslinker between the organic matrix and DDAS NPs. The effects of DDAS on the thermal and mechanical properties and the curing kinetics of the photocured coatings were investigated. The addition of BMI increased the Tg of the coatings from 40 to 78 degrees C with respect to the base formulation. The presence of BMI improved the distribution of DDAS NPs in the organic matrix. Moreover, the thermal and the flame retardancy of the hybrid coatings were improved. While the LOI of the base formulation was found as 21.6%, with the introduction of DDAS NPs the LOI of the hybrid coatings was increased up to 24.1%. (C) 2017 Elsevier Ltd. All rights reserved.
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    New horizon in phospha-michael reaction: Ultrafast double addition of P-H bond-bearing nucleophiles to alectron-deficient triple bonds and its use for functional monomer synthesis and polymer modification
    (2023-01-01) ÇAKMAKÇI, EMRAH; FINDIK, VOLKAN; ERDEM, SAFİYE; Sagdic G., Daglar O., ÇAKMAKÇI E., FINDIK V., ERDEM S., Tunca Ü., Günay U. S., Durmaz H.
    In this work, a novel, straightforward, robust, fast, and organocatalyst-mediated phospha-Michael reaction (OCPMR) was developed for the addition of phosphorus nucleophiles to electron-deficient alkynes. Several P-H bond-bearing compounds with either fully aliphatic or aromatic units were utilized for this newly developed reaction, and it was found that phosphorous species containing only aromatic groups reacted with activated alkynes within 5 min at room temperature. The reaction led to a fast double-addition of the phosphorous compounds to the triple bond of the alkynes. An in-depth analysis of the reaction mechanism and selectivity of this OCPMR was performed using computational methods. Using the developed method, double-phosphorylated allyl-functional monomers were synthesized and subsequently used for the synthesis of linear and crosslinked polymers via thiol-ene photopolymerization. The thermoset materials exhibited LOI values as high as 26.4%. We also showed that polyesters having electron-deficient triple bonds could be easily functionalized with the P-H bond-bearing compounds. The synthetic method proposed herein promises easy and fast P-C bond formation under mild reaction conditions, and it is a straightforward method for the synthesis of phosphorus-containing monomers, linear or crosslinked polymers, and for polymer post-functionalization. We believe this feature will be of great interest not only to material chemists and polymer scientists but also to organic chemists, pharmaceutical researchers, etc.