Journal of Polymer Science Part A: Polymer Chemistry

Cover image for Vol. 51 Issue 13

1 July 2013

Volume 51, Issue 13

Pages i–iv, 2731–2978

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      Cover Image, Volume 51, Issue 13 (pages i–ii)

      Article first published online: 30 MAY 2013 | DOI: 10.1002/pola.26766

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      Biomass-derived furfuryl methacrylate (FMA) is successfully polymerized for the first time by anionic polymerization to produce highly isotactic (97%), moderately syndiotactic (70%), or atactic poly(furfuryl methacrylate) (PFMA), depending on initiator structure and reaction conditions, as presented by Jianghua He, Yuetao Zhang, and Eugene Y. X. Chen on page 2793. Thermal properties of the PFMA materials are strongly affected by the polymer tacticity. The PFMA tacticity also greatly affects the amount of stable carbonaceous materials it produces when heated to high temperatures (650 _C). Using the Diels–Alder “click reaction” between the reactive furfuryl group within the PFMA polymers and a bismaleimide, thermo-reversible, self-healing smart polymers are successfully prepared.

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      Inside Cover, Volume 51, Issue 13 (pages iii–iv)

      Article first published online: 30 MAY 2013 | DOI: 10.1002/pola.26767

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      Highly fluorinated phosphonium salts bearing a polymerizable group are synthesized and incorporated into photopolymerizable systems, as presented on page 2782 by Paul J. Ragogna et al. This imparted hydrophobic behavior to the cured films despite the presence of ionic charges. A structure–activity relationship is found between the structure and architecture of the phosphonium core and its hydrophobic performance. Time-of-flight secondary ion mass spectrometry analysis confirms the presence of the fluorinated species at the polymer/air interface.

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      Polypeptoids: A perfect match for molecular definition and macromolecular engineering? (pages 2731–2752)

      Robert Luxenhofer, Corinna Fetsch and Arlett Grossmann

      Article first published online: 19 APR 2013 | DOI: 10.1002/pola.26687

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      Polypeptides are nature's precision polymers that exhibit sequence-specific functions such as catalysis and molecular recognition. Other properties, such as secondary structure formation or smart responses to external triggers, require defined but not sequence-specific polymers. Polypeptoids have been shown to be able to address these issues. A comprehensive overview on the different synthetic routes toward molecularly defined polypeptoids and polypeptoids with narrow dispersities as well as their properties is given.

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      Synthesis and characterization of regioregular poly(3-dodecyltellurophene) (pages 2753–2758)

      Woo-Hyung Lee, Sang Kyu Lee, Won Suk Shin, Sang-Jin Moon and In-Nam Kang

      Article first published online: 11 APR 2013 | DOI: 10.1002/pola.26688

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      A new poly(3-dodecyltellurophene) (P3DDTe) is synthesized through a Suzuki polymerization reaction, and optoelectronic properties of P3DDTe are described.

  4. Articles

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    1. Synthesis and phase behaviors of side-chain liquid-crystalline polymers containing azobenzene mesogen with the different length alkyl tail (pages 2759–2768)

      Sheng Chen, Aihua Ling and Hai-Liang Zhang

      Article first published online: 17 APR 2013 | DOI: 10.1002/pola.26683

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      A series of side chain liquid-crystal polymers, poly [6-[4-(4′′-n-alkyl benzoateazo)phenoxy]-hexylmethacrylate]s (PMazoCOORm), where m is the number of carbons of alkyl tails (m = 1, 2, 3, 4, 5, 6, 8, 10, 14, and 18), are prepared by two synthetic methods. The phase behaviors of the polymers are investigated by a combination of techniques, including differential scanning calorimetry, polarized optical microscopy, and 1D small-angle X-ray scattering. The experiment results indicate that the length of alkyl tails play an important role in the phase behaviors of these polymers.

    2. Amphiphilic diblock copolymers based on poly(2-ethyl-2-oxazoline) and poly(4-substituted-ε-caprolactone): Synthesis, characterization, and cellular uptake (pages 2769–2781)

      Kang-Yu Peng, Shiu-Wei Wang and Ren-Shen Lee

      Article first published online: 22 APR 2013 | DOI: 10.1002/pola.26690

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      The synthesis and the micellar characterization of novel amphiphilic block copolymers, based on hydrophilic PEtOz and poly(4-substituted-ɛ-caprolactone) [(e.g., poly(4-methyl-ε-caprolactone) (PMCL) and poly(4-phenyl-ɛ-caprolactone) (PBCL)] is discussed. Amphiphilic PEtOz-b-PMCL and PEtOz-b-PBCL show low cytotoxicity. Doxorubicin hydrochloride (DOX)-loaded micelles facilitate HeLa cell uptake of DOX, and DOX is able to reach intracellular compartments and enter nuclei by endocytosis. PEtOz-b-PM(B)CL can be used for drug delivery.

    3. Fluorinated polymerizable phosphonium salts from PH3: Surface properties of photopolymerized films (pages 2782–2792)

      Ryan Guterman, Bradley M. Berven, T. Chris Corkery, Heng-Yong Nie, Mike Idacavage, Elizabeth R. Gillies and Paul J. Ragogna

      Article first published online: 19 APR 2013 | DOI: 10.1002/pola.26692

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      Highly fluorinated phosphonium salts bearing a polymerizable group are synthesized and incorporated into photopolymerizable systems. This imparts hydrophobic behavior to the cured films, despite the presence of ionic charges. A structure--activity relationship is found between the structure and architecture of the phosphonium core and its hydrophobic performance. Time-of-flight secondary ion mass spectrometry (TOF-SIMS) analysis confirms the presence of the fluorinated species at the polymer/air interface.

    4. Spotlight Article

      Anionic polymerization of biomass-derived furfuryl methacrylate: Controlling polymer tacticity and thermoreversibility (pages 2793–2803)

      Jianghua He, Yuetao Zhang and Eugene Y. X. Chen

      Article first published online: 9 APR 2013 | DOI: 10.1002/pola.26679

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      Biomass-derived furfuryl methacrylate is successfully polymerized for the first time by anionic polymerization, leading to tactic or atactic polymers that exhibit sharply different thermal properties related to crosslinking and stable carbonaceous materials formation.

    5. Synthesis and tailoring phase behavior of mesogen jacketed liquid crystalline copolymers based on 2, 5-bis[(4-alkoxyphenyl)oxycarbonyl]styrenes (pages 2804–2816)

      Sheng Chen, Jun Qiu, He-Lou Xie and Hai-Liang Zhang

      Article first published online: 22 APR 2013 | DOI: 10.1002/pola.26660

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      Three series of binary copolymers with high molecular weights are prepared via free-radical polymerization based on 2, 5-bis[(4-alkoxyphenyl)oxycarbonyl]styrenes (M-OCm), where m is the number of carbons of alkyl tails (m = 1, 4, and 18). The phase behaviors of copolymers are studied by differential scanning calorimetry (DSC), polarized light microscopy (POM), and 1D wide-angle X-ray diffraction (WAXD). The experiment results show that the self-assembly behavior of mesogen-jacketed liquid crystalline copolymers strongly depends on the composition and the alkyl length, due to the competition among the steric effect, the microphase separation, and the driving force of the entropy.

    6. Block copolymers prepared by polymeric radical addition cross-coupling reaction to different double bonds (pages 2817–2823)

      Chengyu Zhang and Qi Wang

      Article first published online: 31 MAR 2013 | DOI: 10.1002/pola.26669

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      Block copolymers (P1-X-P2) are synthesized by the radical addition cross-coupling reaction between two different polymeric radicals generated in situ by two different bromopolymers (P1-Br and P2-Br) in the presence of ethyl dithiobenzoate or 1,1-diphenylethylene (X), which cannot be prepared by the normal atom transfer radical coupling (ATRC) of the mixture of P1-Br and P2-Br.

    7. Synthesis and characterization of resorcinarene-centered amphiphilic A8B4 miktoarm star copolymers based on poly(ε-caprolactone) and poly(ethylene glycol) by combination of CROP and “click” chemistry (pages 2824–2833)

      Chen Gao, Ying Wang, Pengfei Gou, Xia Cai, Xiaodong Li, Weipu Zhu and Zhiquan Shen

      Article first published online: 31 MAR 2013 | DOI: 10.1002/pola.26670

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      Well-defined resorcinarene-centered A8B4 miktoarm star copolymers are synthesized. These copolymers can self-assemble into spherical micelles in aqueous solutions with resorcinarene moieties on the hydrophilic/hydrophobic interface.

    8. Hydrophilic CO2-based biodegradable polycarbonates: Synthesis and rapid thermo-responsive behavior (pages 2834–2840)

      Lin Gu, Yusheng Qin, Yonggang Gao, Xianhong Wang and Fosong Wang

      Article first published online: 2 APR 2013 | DOI: 10.1002/pola.26672

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      Hydrophilic CO2-based biodegradable polycarbonates are designed and prepared. The resultant terpolymers are more hydrophlilic than poly(propylene carbonate) (PPC); water contact angles of the terpolymers with 4.2--23.6% of ME3MO units in the terpolymers (FME3MO) are 68--25°. Furthermore, the terpolymers with >25.8% of FME3MO show rapid and reversible thermo-responsive properties in water, whose lower critical solution temperature (LCST) ranges from 7 to 36.2 °C.

    9. Facile synthesis and electro-optic activities of new polycarbonates containing tricyanofuran-based nonlinear optical chromophores (pages 2841–2849)

      Guowei Deng, Shuhui Bo, Tingting Zhou, Heyan Huang, Jieyun Wu, Jialei Liu, Xinhou Liu, Zhen Zhen and Ling Qiu

      Article first published online: 2 APR 2013 | DOI: 10.1002/pola.26673

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      Electro-optic (EO) polycarbonates are prepared through copolymerization of diol nonlinear optical chromophores and bisphenol A with bisphenol A bis(chloroformate) in solution. The obtained polycarbonates exhibit good film-forming properties and good thermal stability. The poled films of the resultant electro-optic polycarbonates reveal the maximum EO coefficient of 75 pm/V. The obtained poled films also possess better temporal stability. These good performances endow the resultant EO polycarbonates with device application in photonics.

    10. Thermoresponsive gels based on ABA triblock copolymers: Does the asymmetry matter? (pages 2850–2859)

      Mark A. Ward and Theoni K. Georgiou

      Article first published online: 31 MAR 2013 | DOI: 10.1002/pola.26674

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      Thermoresponsive ABA triblock copolymers form flower-like micelles at room temperature and gels at higher temperatures and concentrations. This is influenced by the asymmetry of the triblocks; the more symmetric the architecture, the lower the sol--gel temperature.

    11. New photo-induced thiol-ene crosslinked films based on linear methacrylate copolymer polythiols (pages 2860–2868)

      Qian Zhang, Ji Won Hwang, Kyung Nam Kim, Hyun Wook Jung, Seung Man Noh and Jung Kwon Oh

      Article first published online: 31 MAR 2013 | DOI: 10.1002/pola.26675

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      New photo-induced thiol-ene crosslinked films composed of linear methacrylate copolymer polythiols are reported, exhibiting rapid cure, a uniform network, and enhanced mechanical properties for surface coatings applications.

    12. Spotlight Article

      Synthesis and bifunctional asymmetric organocatalysis of helical poly(phenylacetylene)s bearing cinchona alkaloid pendants via a sulfonamide linkage (pages 2869–2879)

      Hiroki Iida, Zhenglin Tang and Eiji Yashima

      Article first published online: 19 APR 2013 | DOI: 10.1002/pola.26678

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      Novel helical poly(phenylacetylene)s with amino-functionalized cinchona alkaloid pendant groups connecting to the phenyl rings through a sulfonamide linkage are synthesized. The optically active sulfonamide-linked polymers adopt a helical conformation with an excess of one-handedness, and efficiently catalyze the enantioselective aza-Michael addition of aniline to chalcone, thus affording a remarkably higher enantioselectivity (up to 86% ee) than those of corresponding monomers and nonhelical polymers.

    13. Synthesis and characteristics of poly(N-isopropylacrylamide-co-methacrylic acid)/Fe3O4/poly(N-isopropylacrylamide-co-methacrylic acid) two-shell thermosensitive magnetic composite hollow latex particles (pages 2880–2891)

      Chia-Fen Lee, Yu-Cheng Wang and Wen-Yen Chiu

      Article first published online: 17 APR 2013 | DOI: 10.1002/pola.26680

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      Poly(N-isopropylacrylamide-methylacrylate acid) (poly(NIPAAm-MAA))/Fe3O4/poly (NIPAAm-MAA) two-shells magnetic composite hollow latex particles are synthesized by a four-step reaction. Many factors, such as reactant concentration, monomer ratio, and pH value, significantly influence the morphology of composite latex particles. Transmission electron microscopy is used to observe the appearance morphology and cross-section morphology of magnetic composite latex particles. The results show that the latex particles possess a hollow structure.

    14. Polymethylene-block-polystyrene copolymers: A new synthetic approach using a combination of polyhomologation and reversible addition-fragmentation chain-transfer polymerization and their microfibers and microspheres fabricated through electrospinning process (pages 2892–2899)

      Xin Wang, Jin-Ping Gao, Qiao-Ling Zhao, Jin Huang, Guo-Liang Mao, Wei Wu, Ying-Nan Ning and Zhi Ma

      Article first published online: 11 APR 2013 | DOI: 10.1002/pola.26681

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      Well-defined polymethylene-b-polystyrene (PM-b-PS) diblock copolymers are synthesized via a combination of polyhomologation of ylides and reversible addition-fragmentation chain-transfer polymerization. The terminal thiocarbonylthio group of PM-b-PS is efficiently transformed into the thiol group by aminolysis. The microspheres and microfibers of PM1-b-PS3 are fabricated by an electrospinning process using dimethylformamide (DMF) and DMF-CHCl3 as solvents, and are observed by scanning electron microscopy (SEM).

    15. Ethylene–ethyl acrylate copolymers via ADMET polymerization: Effect of sequence distribution on thermal properties (pages 2900–2909)

      Zi-Long Li, Lei Li, Xin-Xing Deng, An Lv, Chun-Hao Wang, Fu-Sheng Du and Zi-Chen Li

      Article first published online: 11 APR 2013 | DOI: 10.1002/pola.26682

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      Periodic and random ethylene-ethyl acrylate copolymers are synthesized via acyclic diene metathesis copolymerization. Differential scanning calorimetry results indicate that copolymers with low ethyl acrylate content and regular primary structure exhibit better crystallinity.

    16. Effect of side-chain positions on morphology and photovoltaic properties of phenazine-based donor–acceptor copolymers (pages 2910–2918)

      Ying Li, Yingying Fu, Hui Tong, Zhiyuan Xie and Lixiang Wang

      Article first published online: 17 APR 2013 | DOI: 10.1002/pola.26684

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      Two phenazine-based donor--acceptor copolymers (P1 and P2) are synthesized. Although the effects of the position of alkoxy groups attached to the phenazine unit on optical and electrochemical properties of copolymers are limited, very different copolymer/PC71BM blend morphologies and photovoltaic performance are observed.

    17. Controlled/living copolymerization of styrene and acrylamide in DMF with Fe/TMEDA complex as catalyst (pages 2919–2924)

      Guo-Xiang Wang, Mang Lu, Zhao-Hui Hou, Jing Li, Ming Zhong and Hu Wu

      Article first published online: 9 APR 2013 | DOI: 10.1002/pola.26685

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      Copolymers of poly(styrene-co-acrylamide) (PSt-co-AM) are synthesized by single electron transfer-living radical polymerization (SET-LRP) at 25 °C in N,N-dimethylformamide (DMF) using CCl4 as the initiator with the Fe(0)/tetramethylethylenediamine (TMEDA) catalytic system. The SET-LRP technique is successfully developed with the aim of reducing the catalyst concentration. The polymerization is performed at an ambient temperature. The macroinitiator has a Mn,GPC of 4700 g/mol and a polydispersity index of 1.16, with the resulting copolymer having an experimentally determined Mn,GPC of 21,500 g/mol and a polydispersity index of 1.60. The gel permeation chromatography (GPC) traces indicate an extremely high initiation efficiency with the resulting copolymer.

    18. Synthesis and electrochromic properties of aromatic polyetherimides based on a triphenylamine-dietheramine monomer (pages 2925–2938)

      Sheng-Huei Hsiao, Hui-Min Wang, Pei-Chi Chang, Yu-Ruei Kung and Tzong-Ming Lee

      Article first published online: 17 APR 2013 | DOI: 10.1002/pola.26686

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      A series of electroactive polyetherimides (PEIs) are synthesized from 4,4′'-bis(p-aminophenoxy)triphenylamine and various aromatic dianhydrides. Insertion of a phenoxy spacer between the triphenylamine unit and the imide ring decreases the oxidation potentials and increases the electrochemical stability of the polyimides. All the PEIs exhibit ambipolar electrochemical and electrochromic behavior. The PEI films exhibit reversible electrochemical oxidation accompanied by strong color changes that can be switched through modulation of the applied potential.

    19. One-pot synthesis of conjugated poly(3-hexylthiophene)-b-poly(phenyl isocyanide) hybrid rod–rod block copolymers and its self-assembling properties (pages 2939–2947)

      Zong-Quan Wu, Cheng-Gang Qi, Na Liu, Ying Wang, Jun Yin, Yuan-Yuan Zhu, Long-Zhen Qiu and Hong-Bo Lu

      Article first published online: 17 APR 2013 | DOI: 10.1002/pola.26689

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      A series of molecular weights and composition-tunable conjugated rod--rod block copolymers, poly(3-hexylthiophene)-b-poly(phenyl isocyanide) (P3HT-b-PPI), are synthesized in the presence of Ni(dppp)Cl2 as a single catalyst in one pot. Spherical aggregates and an amorphous state are observed in tetrahydrofuran and CHCl3 solutions, respectively. The atomic force microscopy reveals that the block copolymers can self-assemble into nanofibrils from CHCl3 on the substrate. The unique features warrant the resultant copolymers' potential study in organic photovoltaic and other electronic devices.

    20. Spotlight Article

      Modulation of electronic properties of π-conjugated copolymers derived from naphtho[1,2-b:5,6-b′]dithiophene donor unit: A structure-property relationship study (pages 2948–2958)

      Pranabesh Dutta, Hanok Park, Minjae Oh, Sushil Bagde, In Nam Kang and Soo-Hyoung Lee

      Article first published online: 28 APR 2013 | DOI: 10.1002/pola.26691

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      New naphtho[1,2-b:5,6-b′]dithiophene-containing donor--acceptor conjugated copolymers are designed and developed for application in polymer solar cells. The effect of different electron--acceptor groups on the optoelectronics and photovoltaic properties of the copolymers are evaluated and described.

    21. RAFT polymerization of a novel allene-derived asymmetrical divinyl monomer: A facile strategy to alkene-functionalized hyperbranched vinyl polymers with high degrees of branching (pages 2959–2969)

      Youmei Bao, Guorong Shen, Xiaohui Liu and Yuesheng Li

      Article first published online: 9 APR 2013 | DOI: 10.1002/pola.26693

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      Hyperbranched vinyl polymers with high degrees of branching and numerous functional pendent allene groups are successfully prepared via reversible addition fragmentation chain transfer (RAFT) polymerization of a new allene-derived asymmetrical divinyl monomer.

    22. Nitroxide mediated synthesis of low dispersity random copolymers for low-loss optical waveguides (pages 2970–2978)

      Zi Jun Wang and Milan Maric

      Article first published online: 19 APR 2013 | DOI: 10.1002/pola.26694

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      Photocrosslinkable optical waveguides consisting of well-defined glycidyl methacrylate/pentafluorostyrene (GMA/PFS) random copolymers synthesized by nitroxide mediated polymerization (NMP) are fabricated in this study. As features ∼1 μm are approached, lower polymer dispersity (w/n) afforded by NMP reduces the line edge roughness (LWR).

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