Journal of Polymer Science Part A: Polymer Chemistry

Cover image for Vol. 50 Issue 4

15 February 2012

Volume 50, Issue 4

Pages i–iv, 615–830

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    1. Top of page
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    3. Articles
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      Cover Image, Volume 50, Issue 4 (pages i–ii)

      Article first published online: 4 JAN 2012 | DOI: 10.1002/pola.25905

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      Various derivatives of 3,4-propylenedioxythiophene/selenophene having different substituent groups are synthesized electrochemically and the effect of substituents and heteroatoms on the electrochromic and optical properties are presented by Merve İçli-Özkut, Jetmire Mersini, Ahmet M. Önal, and Atilla Cihaner on page 615. The image describes the polymer, poly(3,3-didecyl-3,4-dihydro-2H-selenopheno[3,4-b][1,4]dioxepine, which has superior properties, i.e., lower oxidation potential, high optical contrast value, and solubility, and is designed by replacing bulky substituents and the S atom of the thiophene ring with flexible alkyl chains and a Se atom, respectively. These properties make the polymer a candidate for advanced technological applications of electrochromic materials.

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      Inside Cover, Volume 50, Issue 4 (pages iii–iv)

      Article first published online: 4 JAN 2012 | DOI: 10.1002/pola.25906

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      Electrochemical polymerization in a crystal solid electrolyte solution allows production of electroactive polymers with crystal order, as presented by Hiromasa Goto on page 622. The two polarizing optical microscopy images are optical structures of polybithiophene and poly(ethylene dioxythiophene) (PEDOT) prepared in the crystal electrolyte, showing the crystal order of the two polymers. This is an example of a new synthesis method for obtaining π-conjugated polymers with crystal order and electronic properties.

  2. Articles

    1. Top of page
    2. Cover Image
    3. Articles
    1. Substituent and heteroatom effects on the electrochromic properties of similar systems (pages 615–621)

      Merve İçli-Özkut, Jetmire Mersini, Ahmet M. Önal and Atilla Cihaner

      Article first published online: 28 OCT 2011 | DOI: 10.1002/pola.25047

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      Three eletrochromic polymers, poly(3,4-dihydro-3,3-bis((naphthalen-1-yl)methyl)-2H-thieno[3,4-b][1,4]dioxepine), poly(3,3-dibenzyl-3,4-dihydro-2H-selenopheno[3,4-b][1,4] dioxepine), and poly(3,3-dibenzyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine), were synthesized electrochemically and the effect of substituents and heteroatoms on the electrochromic properties were investigated for the similar systems. All polymers show electrochromism from a colored state when neutralized to transmissive when oxidized. It was observed that, instead of using bulky substituents, flexible alkyl chains can also be used to increase optical contrast. Thus, using flexible alkyl groups will not only increase the optical contrast value but also enhance the solubility of corresponding polymer.

    2. Electrochemical Polymerization in crystal—preparation of polybithiophene with crystal order (pages 622–628)

      Hiromasa Goto

      Article first published online: 12 NOV 2011 | DOI: 10.1002/pola.25071

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      Electrochemical polymerization in a crystal solid electrolyte solution for obtaining π-conjugated polymers having crystals order was achieved. The polymers thus prepared show electroactive properties.

    3. Polysiloxanes polymers with hyperbranched structure and multivinyl functionality (pages 629–637)

      Yu Zheng, Kristofer J. Thurecht and Wenxin Wang

      Article first published online: 16 NOV 2011 | DOI: 10.1002/pola.25072

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      Hyperbranched polysiloxane polymers with multivinyl functionality were designed and synthesized through a “one-step and one-pot” deactivation enhanced atom transfer polymerization (DE-ATRP) approach from the copolymerization of polydimethylsiloxane (PDMS) macromonomers, and divinylbenzene (DVB). Even at DVB concentrations as high as 80 mol % in the feed, 65% yield of hyperbranched polymer could be obtained without gelation because the DE-ATRP suppressed the rapid formation of macronetwork structures. Furthermore, the oil thickening experiments demonstrate that this hyperbranched polymer can act as a well-controlled viscosity-modifier for silicone oils, which potentially will have important application in coating, cosmetic and pharmaceutical products.

    4. Living syndiospecific polymerization of propylene promoted by C1-symmetric titanium complexes activated by dried MAO (pages 638–648)

      Ying-Yun Long, Yong-Xia Wang, Jing-Yu Liu and Yue-Sheng Li

      Article first published online: 12 NOV 2011 | DOI: 10.1002/pola.25073

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      In the presence of dried MAO, the newly designed C1-symmetric titanium complex with bulky substituent tert-butyl ortho to alkyl oxygen promotes living polymerization of propylene with improved catalytic activity at ambient temperature, producing high molecular weight syndiotactic polypropylene (rrrr 90.2%) with narrow molecular weight distributions (Mw/Mn ≤1.22), via a propagation of 1,2-insertion of monomer and chain-end control mechanism.

    5. Side-chain effects on phenothiazine-based donor–acceptor copolymer properties in organic photovoltaic devices (pages 649–658)

      Young-Hoon Seo, Woo-Hyung Lee, Jong-Hyeok Park, Cheolbeom Bae, Yongtaek Hong, Jong-Wook Park and In-Nam Kang

      Article first published online: 12 NOV 2011 | DOI: 10.1002/pola.25074

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      The new copolymers with phenothiazylene vinylene donors and DTBT acceptors were synthesized and the effects of side chains on the photophysical, electrochemical, and OPV properties were studied.

    6. Synthesis of peroxide-curable butyl rubber via suzuki–miyaura coupling of halogenated butyl rubber with 4-vinylphenylboronic acid (pages 659–664)

      Katsuhiko Takenaka, Masumi Suzuki, Hiroki Takeshita, Masamitsu Miya, Tomoo Shiomi, Kenji Tamamitsu and Toshihiro Konda

      Article first published online: 12 NOV 2011 | DOI: 10.1002/pola.25075

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      The Suzuki–Miyaura coupling reaction of brominated butyl rubber with a mixture of 4-vinylphenylboronic acid and phenylboronic acid was carried out in THF under various conditions using a cyclopalladated complex as a catalyst. A 4-vinylphenyl and phenyl group could be introduced to butyl rubber in a high yield to give peroxide-curable butyl rubber with aimed crosslinking density.

    7. Synthesis and characterization of rigid functional anionic polyelectrolytes: Block copolymers and star homopolymers (pages 665–674)

      Maria Rikkou-Kalourkoti, Eleni Kassi and Costas S. Patrickios

      Article first published online: 23 NOV 2011 | DOI: 10.1002/pola.25076

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      Stepwise reversible addition–fragmentation chain transfer polymerization was used, for the first time, to prepare linear amphiphilic diblock copolymers and star homopolymers with hydrophobic cyclolinear blocks or arms, respectively. Selective hydrolysis transformed the cyclolinear hydrophobic units to cyclolinear carboxylic acid units, yielding linear ampholytic diblock copolymers and polyanionic star homopolymers with cyclolinear carboxylic acid-bearing blocks or arms.

    8. QCM sensing of a chemical nerve agent analog via electropolymerized molecularly imprinted polythiophene films (pages 675–685)

      Aileen V. Vergara, Roderick B. Pernites, Shemaiah Pascua, Christina A. Binag and Rigoberto C. Advincula

      Article first published online: 19 NOV 2011 | DOI: 10.1002/pola.25077

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      A quartz crystal microbalance detection of a chemical nerve agent analog using a molecularly imprinted polythiophene film is demonstrated. The cyclic voltammetric electrodeposition method has enabled the direct interfacing of the imprinted film onto the transducer surface. The sensor film has revealed sensitivity and selectivity toward the imprinted molecule with a limit of detection and a limit of quantification of ∼ 60 and ∼ 197 μM, respectively and linear sensing range between 125 and 250 μM concentration of the analyte.

    9. Synthesis, morphology, and field-effect transistor characteristics of new crystalline–crystalline diblock copolymers of poly(3-hexylthiophene-block-steryl acrylate) (pages 686–695)

      Jung-Chuan Lin, Wen-Ya Lee, Chi-Ching Kuo, Chaoxu Li, Raffaele Mezzenga and Wen-Chang Chen

      Article first published online: 12 NOV 2011 | DOI: 10.1002/pola.25078

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      Small- and wide- angle X-ray scattering indicated the presence of both poly(3-hexyl thiophene) (P3HT) and poly(stearyl acrylate) (PSA) crystalline domains and the presence of microphase separation among blocks. The transmission electron microscopy (TEM) and atomic force microscopy (AFM) results revealed that the diblock copolymers cast from chlorobenzene, tended to form needle-like morphologies. The field- effect mobilities of the diblock copolymers deposited on untreated SiO2 substrates decreased with increasing PSA block length. In a sharp contrast, the mobilities enhanced with increasing PSA content when the P3HT-b-PSA was deposited on phenyltrichlorosilane (PTS)-treated substrates.

    10. Synthesis of fluorene-based hyperbranched polymers for solution-processable blue, green, red, and white light-emitting devices (pages 696–710)

      Hung-Min Shih, Ren-Chi Wu, Ping-I Shih, Chien-Lung Wang and Chain-Shu Hsu

      Article first published online: 19 NOV 2011 | DOI: 10.1002/pola.25080

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      Polymer light-emitting devices using the hyperbranched polymers were investigated by using host–guest doped system. Hb-TF as the polymeric host doped with Os(fptz)2(PPh2Me2)2 as guest allowed saturated red electrophosphorescent devices to be obtained. By adding BFBT as the green dopant in the PFO:Hb-BFTBT blend, PFO as the host, and Hb-BFTBT as the guest, white polymer light-emitting devices were obtained.

    11. Ligand-free Cu(0)-mediated controlled radical polymerization of methyl methacrylate at ambient temperature (pages 711–719)

      Wenxiang Wang, Zhengbiao Zhang, Yang Wu, Jian Zhu, Zhenping Cheng, Nianchen Zhou, Wei Zhang and Xiulin Zhu

      Article first published online: 19 NOV 2011 | DOI: 10.1002/pola.25081

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      Ligand-free Cu(0)-mediated polymerization of methyl methacrylate (MMA) was realized by the selection of ethyl-2-bromo-2-phenylacetate as initiator at ambient temperature. The polymerization can reach up to 95% conversion within 5 h with dimethyl sulfoxide (DMSO) as solvent, while keeping manners of the controlled radical polymerization. Extensive investigation of this system revealed that for a well-controlled Cu(0)-mediated polymerization of MMA, the initiator should be selected with the structure as alkyl 2-bromo-2-phenylacetate, and the solvent should be DMSO or N,N-dimethylformamide.

    12. Regiospecific cationic polymerization of spiroorthoesters with different cyclic ether ring sizes (pages 720–728)

      Ying-Gev Hsu, Wei-Yang Lin, Wei-Lun Hsieh and Shung-Yao Tsai

      Article first published online: 26 NOV 2011 | DOI: 10.1002/pola.25827

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      Spiroorthoesters (SOEs) I and II underwent regiospecific polymerization to yield trans form of stereoregular poly(ether esters) III and V, respectively, when using 9-phenyl-9,10-dihydroanthracen-10-ylium cation as an initiator. I and II underwent regiospecific polymerization through different mechanisms to afford cis form IV and trans form VI stereoregular poly(ether esters) when using SnCl4 as an initiator. The polymerization mechanisms of SOEs proceeded in the regiospecific manner were determined in terms of the relation among sterostructures of SOEs and polymers thus formed, the steric energy of monomers, and free energy difference in the transition state of reaction.

    13. 3-miktoarm star terpolymers using triple click reactions: Diels–Alder, copper-catalyzed azide-alkyne cycloaddition, and nitroxide radical coupling reactions (pages 729–735)

      Ufuk Saim Gunay, Hakan Durmaz, Eda Gungor, Aydan Dag, Gurkan Hizal and Umit Tunca

      Article first published online: 26 NOV 2011 | DOI: 10.1002/pola.25828

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      Well-defined linear furan-protected maleimide terminated poly(ethylene glycol), tetramethylpiperidine-1-oxyl-terminated poly(ε-caprolactone), and azide-terminated polystyrene or -poly(N-butyl oxanorbornene imide) were ligated to an orthogonally functionalized core (1) in a two-step reaction mode through triple click reactions.

    14. Preparation of poly(methyl methacrylate)–poly(acrylonitrile-co-butadiene) core–shell nanoparticles (pages 736–749)

      Hui Wang, Qinmin Pan, Michael Hammond and Garry L. Rempel

      Article first published online: 29 NOV 2011 | DOI: 10.1002/pola.25829

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      The poly(methyl methacrylate)–poly(acrylonitrile-co-butadiene) (PMMA–NBR) core–shell structured nanoparticles were successfully prepared using a two-stage semibatch microemulsion polymerization system with PMMA and NBR as the core and shell, respectively. The microemulsion system was stabilized by Gemini surfactant 12-3-12. The obtained PMMA–NBR core–shell nanoparticles are small and show spherical morphology. The obtained core–shell nanoparticles have important features illustrated by fast latex hydrogenation capabilities in the absence of any organic solvent.

    15. Highly reactive polyisobutylenes via AlCl3OBu2-coinitiated cationic polymerization of isobutylene: Effect of solvent polarity, temperature, and initiator (pages 750–758)

      Irina V. Vasilenko, Dmitriy I. Shiman and Sergei V. Kostjuk

      Article first published online: 26 NOV 2011 | DOI: 10.1002/pola.25830

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      H2O/AlCl3OBu2 initiating system can be successfully used for the synthesis of isobutylene oligomers with high content of vinylidene end groups (up to 96%) in nonpolar media (toluene, n-hexane) and elevated reaction temperatures (from −20 to 30 °C).

    16. Cyclodextrin-overhanging hyperbranched core-double-shell miktoarm architectures: Synthesis and gradient stimuli-responsive properties (pages 759–771)

      Wei Tian, Xiaoyan Lv, Chengguang Mu, Weihong Zhang, Jie Kong, Yuyang Liu and Xiaodong Fan

      Article first published online: 26 NOV 2011 | DOI: 10.1002/pola.25831

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      Cyclodextrin-overhanging hyperbranched core-double-shell miktoarm architectures possess three-stage phase transition behaviors based on the double-shell architectures, composed of pH-responsive PDEAEMA homoarms as the inner shell and different temperature-responsive PNIPAm/PDMAEMA miktoarms as the outmost shell.

    17. Synthesis of fac-Ir(ppy)3 end-functionalized poly(1,3-cyclohexadiene): single monomer addition of fac-Ir(ppy)2(vppy) for well-controlled polymer synthesis (pages 772–779)

      Itaru Natori and Shizue Natori

      Article first published online: 19 NOV 2011 | DOI: 10.1002/pola.25832

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      Synthesis of poly(1,3-cyclohexadiene) (PCHD) whose end is functionalized by fac-Ir(ppy)3 (ppy = 2-phenylpyridyl) was achieved by using (living) anionic polymerization of 1,3-cyclohexadiene. Complexation of the pyridyl ring protected the α-carbons of fac-Ir(ppy)2(vppy) [vppy = 2-(4-vinylphenyl)pyridyl] from the reaction of the anionic polymer. Only one molecule of fac-Ir(ppy)2(vppy) reacted with the carbanion of poly(1,3-cyclohexadienyl)lithium and was selectively incorporated into an end of PCHD.

    18. Nitroxide-mediated controlled radical polymerizations of styrene derivatives (pages 780–791)

      Patrick J. M. Stals, Trang N. T. Phan, Didier Gigmes, Tim F. E. Paffen, E. W. Meijer and Anja R. A. Palmans

      Article first published online: 28 NOV 2011 | DOI: 10.1002/pola.25833

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      Several (protected) amine and alcohol functionalized styrene monomers were synthesized via readily accessible synthetic routes. The controlled radical copolymerization of these functionalized styrene monomers with styrene was performed using two alkoxyamines, namely N-(2-methylpropyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxylprop-2-yl)hydroxylamine (MAMA-SG1) and N-tert-butyl-N-(2-methyl-1-phenylpropyl)-O-(1-phenylethyl)hydroxylamine. The obtained copolymers showed low polydispersities, controlled molecular weights and a random topology. The thermal properties of the polymers were determined with differential scanning calorimetry. All polymers were amorphous and showed glass transition temperatures between 40 and 111 °C. Deprotection of the copolymers afforded amine or alcohol pendant polystyrenes which were readily functionalized with isocyanates.

    19. Synthetic pathways enables the design of functionalized poly(lactic acid) with pendant mercapto groups (pages 792–800)

      Daniela Pappalardo, Sofia Målberg, Anna Finne-Winstrad and Ann-Christine Albertsson

      Article first published online: 26 NOV 2011 | DOI: 10.1002/pola.25834

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      Functionalized poly(lactic acid) with sulfur-protected groups along the chain was synthesized with the final aim to obtain materials for reversible and degradable self-assembly systems. Because of high versatility of the sulfur chemistry, the synthesized polyester may be used as building blocks for the synthesis of a wide range of functionalized aliphatic polyesters by several postmodification strategies and expand the applicability of polyester materials in the biomedical field.

    20. Synthesis and polymerizations of phosphonated-bis(methacrylamide)s for dental applications (pages 801–810)

      Burcin Akgun, Emre Savci and Duygu Avci

      Article first published online: 28 NOV 2011 | DOI: 10.1002/pola.25835

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      Novel phosphonate and phosphonic acid-containing bis(methacrylamide)s based on t-butyl α-hydroxymethacrylate-ether dimer were synthesized, evaluated in terms of homo- and copolymerization reactivity, hydrolytic stability, acidity and interaction with hydroxyapatite and found to show potential to be used in dental materials.

    21. Successive SET-LRP and ATRP synthesis of ferrocene-based PPEGMEA-g-PAEFC well-defined amphiphilic graft copolymer (pages 811–820)

      Sujuan Zhai, Jing Shang, Dong Yang, Songyang Wang, Jianhua Hu, Guolin Lu and Xiaoyu Huang

      Article first published online: 26 NOV 2011 | DOI: 10.1002/pola.25836

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      A series of well-defined amphiphilic graft copolymers bearing hydrophilic poly[poly (ethylene glycol) methyl ether acrylate] backbone and hydrophobic ferrocenyl-based poly(2-acryloyloxyethyl ferrocenecarboxylate) side chains were synthesized by sequential single-electron-transfer living radical polymerization and atom transfer radical polymerization.

    22. Synthesis and optical characterization of photoactive poly(2-phenoxyethyl acrylate) copolymers containing azobenzene units, prepared by frontal polymerization using novel ionic liquids as initiators (pages 821–830)

      Javier Illescas, Yessica S. Ramirez-Fuentes, Ernesto Rivera, Omar G. Morales-Saavedra, Antonio A. Rodríguez-Rosales, Valeria Alzari, Daniele Nuvoli, Sergio Scognamillo and Alberto Mariani

      Article first published online: 28 NOV 2011 | DOI: 10.1002/pola.25837

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      2-Phenoxyethyl acrylate (2-PEA) was polymerized alone and in the presence of an azobenzene comonomer derived from Disperse Red-1, N-ethyl-N-(2-hydroxyethyl)-4-(4-nitrophenylazo)aniline (MDR-1), using two novel ionic liquids as initiators, tetrabutylphosphonium persulfate (TBPPS) and trihexyltetradecylphosphonium persulfate (TETDPPS), by the frontal polymerization technique. The obtained polymers were characterized by absorption spectroscopy in the UV–vis region. Moreover, the nonlinear optical (NLO) properties of the 2-PEA/MDR-1 copolymers prepared with TBPPS and TETDPPS were performed according to the Z-Scan technique in film. It has been proven that samples with higher MDR-1 content (0.05 mol %) exhibited outstanding cubic NLO activity.

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