Polymerization behaviour of 2,5‐dimethylene‐ 2,5‐dihydrofuran

Itoh, Takahito; Katoh, Ichiro; Satoh, Toshiya; Iwatsuki, Shouji

doi:10.1002/pola.1995.080330915

Cited by 10 publications

(9 citation statements)

References 14 publications

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“…Energy-dispersive X-ray (EDX) analyses of the composite confirm the regular distribution and the ideal alternation of carbon, oxygen, and silicon ( Figure 2). [10,11] The broad signal at d = 40 ppm indicates cross-linked structures in the polymer. [8] The signal at d = 58 ppm due to the methylene group of the monomer has completely disappeared ( Figure 4).…”

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Nanocomposites Prepared by Twin Polymerization of a Single‐Source Monomer

et al. 2007

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We describe herein a new type of polymerization for the synthesis of nanocomposites in which one monomer undergoes two different polymerization reactions simultaneously and on the same timescale. The monomer must be constructed in such a way that two structurally different homopolymers are generated by a single polymerization mechanism. The functionalities of the covalently combined monomers determine whether a monomer unit undergoes cross-linking or linear chain propagation. Because two structurally different polymers are generated from one "mother" monomer, the process should be designated as twin polymerization.We have demonstrated the principle of the method with the cationic polymerizations of tetrafurfuryloxysilane (TFOS) and difurfuryloxydimethylsilane (DFOS; Scheme 1). The functionality of the silane moiety of TFOS for cross-linking is four since all four furfuryloxy substituents can be cleaved hydrolytically; in contrast, DFOS has a functionality of only two since the two Si À C bonds are stable under the reaction conditions. The functionality of the furfuryl component is always greater than two but is difficult to determine because cross-linking and branching reactions take place in cationic processes.Since the formation of the SiO 2 network and the polymerization of furfuryl alcohol (FA) are mechanistically coupled, interpenetrating networks are formed as a polymer blend. As a result of this coupling, the two polymerization processes are synchronized. As shown in Scheme 2, the stepgrowth polymerization is initiated by cleavage of the SiÀOÀC bond. Depending on the point of view, poly(furfuryl alcohol) (PFA) is the condensation by-product of SiO 2 production or SiO 2 is the by-product of PFA production. Both processes are closely associated on the basis of the cationic growth mechanism, as SiO 2 can form only as rapidly as the furfuryloxy unit is cleaved. The energy balance of the polymerization of TFOS outlined in Scheme 2 can be calculated by using the increment method [Eq. (1)- (3); D = bond dissociation energy].[1] The driving force of this reaction is the significant gain in bond energy on going from amorphous SiÀO to crystalline SiÀO and the strength of the H À O bonds in the water molecule formed as a by-product in the condensation of the silanol group. Scheme 2. Cationic polymerization of TFOS. The scheme represents the brutto conversion and does not give information on the mechanism of the partial reaction. Detailed mechanistic studies will be undertaken in future work. [*] S.

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“…The PFA contains a high proportion of conjugated sequences as can be seen from the presence of signals at d = 95, 130, and 155 ppm. [10,11] The broad signal at d = 40 ppm indicates cross-linked structures in the polymer. [8] The signal at d = 58 ppm due to the methylene group of the monomer has completely disappeared ( Figure 4).…”

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Nanocomposites Prepared by Twin Polymerization of a Single‐Source Monomer

et al. 2007

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“…Specifically, the monomers of 2-(9H-carbazol-9-yl)ethyl methacrylate (MAK), 4-(5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl)phenyl methacrylate (MAO), 4-[5-(1-naphthyl)-1,3,4-oxadiazol-2-yl]phenyl methacrylate (mPND), 4-(5phenyl-1,3,4-oxadiazol-2-yl)-1-naphthyl methacrylate (mNPD) and 4-[5-(1-naphthyl)-1,3,4-oxadiazol-2-yl]-1-naphthyl methacrylate (mNND) were studied as potential replacement candidates. The homopolymers and copolymers of MAK and MAO have been previously of interest in this laboratory, 35 as well as other researchers who have studied a variety of phenomena: the fluorescence and energy-migration characteristics of the PMAK homopolymer and its copolymers with various vinyl monomers [36][37][38][39][40][41][42] ; the thermal degradation of MAK-derived homopolymer and its copolymers with methacrylic acid 43 ; the electroluminescence of the MAK monomer residue has been used and investigated in a limited number of OLED systems 44,45 ; PL response of physical blends of PMAK and PMAO that were prepared through reversible addition-fragmentation chain transfer polymerization 46 ; and a nonvolatile flash memory based on a terpolymer of MAK and MAO with a repeat unit that contains an europium complex. 47 With regard to mPND, there is a dearth of information on this monomer for use in OLEDs, 48 while to the best of our knowledge, mNPD and mNND were not synthesized previously.…”

Section: Electronic Structure Calculationsmentioning

confidence: 99%

Rational design of methacrylate monomers containing oxadiazole moieties for single‐layer organic light emitting devices

Zdyrko

Bandera

Tsyalkovsky

et al. 2015

J Polym Sci B Polym Phys

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Methacrylate derived monomers functionalized with pendant oxadiazole moieties were synthesized and copolymerized with carbazole containing monomers to form polymers with electron and hole transporting fragments in the same molecule. Substituents on the oxidazole moiety were varied with the purpose of bandgap tuning and performance optimization when employed in single‐layer organic light emitting devices (OLED). Quantum mechanical calculations of the HOMO‐LUMO levels of the oxidazole derivatives were used to down‐select promising candidates for chemical synthesis and testing in single‐layer OLEDs. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part B: Polym. Phys. 2015, 53, 1663–1673

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“…Both DT and DF, prepared firstly by Winberg et al 11 are so reactive that they give polymeric materials immediately at room temperature like as QM. We have already reported the polymerization behaviors of DF 12 and the substituted DT derivatives 13 14 was synthesized and isolated as crystals at room temperature. However, the report 14 focused only on the conductivity and crystal structures of the charge-transfer complexes with electron donors, but not on the polymerization behaviors.…”

Section: Introductionmentioning

confidence: 99%