Dendritic Hyperbranched Polyethynylenes with the 1,3,5-<i>s</i>-Triazine Moiety

Kim, Chulhee; Chang, Youngkyu; Kim, Jin Seok

doi:10.1021/ma9602031

Cited by 33 publications

(14 citation statements)

References 29 publications

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“…15 The interfacial polymerization of monomer 3 with 4,4' -isopropylidenediphenol produced polymer 4. 16 The polymer was soluble in chloroform, THF, N,N-dimethyl formamide (DMF), and DMSO.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Optical Characterization of Polycyanurates with Pendent Second-Order Nonlinear Optical Chromophores

Shin

Chang

Kim

et al. 1999

Polym J

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ABSTRACT:A new type of thermally stable second-order nonlinear optical (NLO) polycyanurate was synthesized by coupling Disperse Red I to the aryl hydroxyl-containing linear polycyanurate, which was prepared by the interfacial polymerization of 2-(4-(2-tetrahydropyranyloxy)phenyl)-4,6-dichloro-1 ,3,5-s-triazine with bisphenol A and by subsequent deprotection of tetrahydropyranyl groups. The new NLO polycyanurate exhibited a glass transition at 167oC and an initial thermal decomposition at about 300°C. The electro-optic coefficients ofNLO polycyanurate poled at I MV em-1 were 19 pm v-1 at 633 nm, 13 pm y-1 at 830 nm, and 6 pm v-1 at 1.3/lm. High-temperature polymers with second-order nonlinear optical (NLO) chromophores are of great interest as materials for electro-optic modulator and switching application. 1 The characteristics of polymeric skeleton such as thermal stability, high glass transition temperature, and good film property provide polymeric NLO materials with temporal stability of dipole alignment, and lead to facile thin-film process for effective fabrication and operation of integrated electro-optic devices. 2 · 3 One of the most extensively investigated systems is polyimides due to their high Tg and thermal stability. Several polyimide systems were used in prototype electro-optic devices. 4 -6 The synthesis of polyimide, however, generally includes a reaction between reactive diamine and dianhydride for the preparation of poly(amic acid), which then undergoes high-temperature imidization to produce polyimide. Recently, therefore, an introduction ofNLO chromophores to poly(hydroxy imide)s via Mitsunobu reaction has been reported as an efficient route to avoid high temperature imidization process. 7 In this work, we report new thermally stable secondorder NLO polycyanurate which can be prepared under mild interfacial polymerization condition. Cyanurate resins, three dimensional cyanurate networks, have found industrial applications because of their attractive high temperature characteristics. 8 • 9 Linear polycyanurates derived from interfacial polymerization of 2-R-4,6-chloro-s-triazine and aromatic diols possess excellent thermal stability, high Tg, optical transparency, and high solubility in common organic solvents. 10 · 11 Thus, linear polycyanurates can be considered suitable candidates for thermally stable NLO materials.

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“…15 The interfacial polymerization of monomer 3 with 4,4' -isopropylidenediphenol produced polymer 4. 16 The polymer was soluble in chloroform, THF, N,N-dimethyl formamide (DMF), and DMSO.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Optical Characterization of Polycyanurates with Pendent Second-Order Nonlinear Optical Chromophores

Shin

Chang

Kim

et al. 1999

Polym J

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“…This type of polycoupling is often catalyzed by palladium complexes in the presence of amines and has been widely used for the preparation of linear polymers and perfect dendrimers [71,72]. Employing this reaction protocol, hb-PAEs have been prepared from AB 2 -type monomers [73,74]. Putting mutually reactive halide and acetylene groups into a single monomer is, however, a nontrivial job due to the involved synthetic problems such as undesired self-oligomerization.…”

Section: Hyperbranched Poly(aryleneethynylenes) (Hb-paes)mentioning

confidence: 99%

Acetylenes with multiple triple bonds: A group of versatile An-type building blocks for the construction of functional hyperbranched polymers

Häußler

Qin

Tang

2007

Polymer

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AB n -type monomers have been widely used for the synthesis of hyperbranched polymers. These monomers, however, suffer from the problems associated with the tendency of their mutually reactive A and B functional groups toward self-oligomerization. We have explored the possibility of synthesizing hyperbranched polymers using A n -type monomers, which are stable and easy to prepare and handle, with some being even commercially available. In particular, we have tried to open new synthetic routes to hyperbranched polymers using diynes and triynes as monomers. We have developed metallic [TaBr 5 , Cp*Ru(PPh 3 ) 2 Cl, etc.] and nonmetallic catalysts (piperidine, DMF, etc.) for polycyclotrimerization, polycycloaddition and polycoupling of the acetylenic monomers. We have synthesized a variety of new hyperbranched polymers including polyarylenes, polytriazoles and polydiynes with high molecular weights and excellent solubility in high yields. The polymers exhibit an array of functional properties such as sensitive photonic response, high light refractivity, large optical nonlinearity, high thermal stability, strong optical limiting power and unusual aggregation-enhanced light emission. Utilizing these unique properties, we succeeded in generating fluorescent images, honeycomb patterns, polymer nanotubes, ferromagnetic ceramics, and nanoparticle catalysts.

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“…12 Early efforts by Neumann-Rodekirch 28 using the homopolycondensation of diphenyoxytriazines substituted with amines, including p-aminobenzylamine, Nmethyl-p-aminobenzylamine, and masked amines such as acetylaniline, mono-BOC protected hydrazine, and hexane diamine, were conducted in N-methylpyrrolidine at 200-240 8C with the intent of producing stationary phases for chromatography. More recent examples of hyperbranched triazines include work by Kim et al, 39 who prepared hyperbranched triazine polymers by perScheme 9. Different nucleophiles are used to synthesize a dendron.…”

Section: Hyperbranched Moleculesmentioning

confidence: 99%

Dendrimers based on [1,3,5]‐triazines

Steffensen

Hollink

Kuschel

et al. 2006

J. Polym. Sci. A Polym. Chem.

100

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ABSTRACT:A comprehensive and chronological account of dendrimers based on [1,3,5]-triazines is provided. Synthetic strategies to install the triazine through cycloaddition, cyclotrimerization, and nucleophilic aromatic substitution of cyanuric chloride are discussed.Motivations and applications of these architectures are surveyed, including the preparation of supramolecular assemblies in the solution and solid states and their use in medicines, advanced materials, and separations when anchored to solid supports. V

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Dendritic Hyperbranched Polyethynylenes with the 1,3,5-s-Triazine Moiety

Cited by 33 publications

References 29 publications

Synthesis and Optical Characterization of Polycyanurates with Pendent Second-Order Nonlinear Optical Chromophores

Synthesis and Optical Characterization of Polycyanurates with Pendent Second-Order Nonlinear Optical Chromophores

Acetylenes with multiple triple bonds: A group of versatile An-type building blocks for the construction of functional hyperbranched polymers

Dendrimers based on [1,3,5]‐triazines

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