Journal of Polymer Science Part A: Polymer Chemistry

Cover image for Vol. 51 Issue 19

1 October 2013

Volume 51, Issue 19

Pages i–iv, 3985–4239

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      Cover Image, Volume 51, Issue 19 (pages i–ii)

      Article first published online: 28 AUG 2013 | DOI: 10.1002/pola.26893

      Thumbnail image of graphical abstract

      The image represents the formation of polystyrene particles by an uncommon heterocoagulation mechanism, by which small precursor particles, continuously formed throughout the surfactant-free emulsion polymerization, are captured on the surface of large mature particles, contributing to their growth. The resulting spherical particles exhibit a peculiar surface roughness. This mechanism is investigated on page 3997 by Andrew M. Telford, Binh T. T. Pham, Chiara Neto, and Brian S. Hawkett as part of work on a novel, robust approach to produce micrometer-sized polystyrene particles with narrow size distribution in the presence of air. The approach could be easily employed by those not skilled in the art, to produce large quantities of polymer particles for research applications in a simple way.

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      Cover Image, Volume 51, Issue 19 (pages iii–iv)

      Article first published online: 28 AUG 2013 | DOI: 10.1002/pola.26894

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      A novel fluorescence labeling technique is developed for quantification of surface densities of atom transfer radical polymerization (ATRP) initiators on polymer particles by Masakatsu Kasuya, Tatsuo Taniguchi, Ryuhei Motokawa, Michinari Kohri, Keiki Kishikawa, and Takayuki Nakahira on page 4042. Surface ATRP initiators of polymer particles are converted into azide groups by sodium azide, followed by fluorescent labeling with 5-(N, N-dimethylamino)-N'-(prop-2-yn-1-yl)naphthalene-1-sulfonamide by copper-catalyzed azide-alkyne cycloaddition. The surface ATRP initiator densities of anionic polymer particles estimated by the fluorescence labeling technique is in close agreement with that determined by a conventional conductometric titration method. The fluorescence labeling through click chemistry is a versatile technique to quantify the surface ATRP initiator density not only on anionic particles but also on cationic particles.

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      Innovative macromolecular syntheses via isocyanide multicomponent reactions (pages 3985–3991)

      Jonathan G. Rudick

      Article first published online: 26 JUN 2013 | DOI: 10.1002/pola.26808

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      Increased control over polymer structure and novel molecular architectures are being made possible through synthetic strategies involving isocyanide multicomponent reactions. These reactions assemble more than two reaction components into a single product. Multicomponent reactions allow for control over the sequence of monomer addition in condensation polymerization. Isocyanide multicomponent reactions simplify methods for postpolymerization functionalization of polymers and the synthesis of novel dendrimers.

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    1. Side-by-side comparison of dendritic-linear hybrids and their hyperbranched analogs as micellar carriers of chemotherapeutics (pages 3992–3996)

      Yvonne Hed, Yuning Zhang, Oliver C. J. Andrén, Xianghui Zeng, Andreas M. Nyström and Michael Malkoch

      Article first published online: 3 JUL 2013 | DOI: 10.1002/pola.26825

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      Amphiphilic block copolymers are successfully synthesized possessing a hydrophobic dendritic component based on the bis-MPA monomer and a hydrophilic linear polyethylene glycol (PEG) component. The hybrids were either conjured in small scale using robust click reactions between perfect dendrons and linear PEG or multigram polycondensation of hyperbranched blocks from PEG. In all cases, the amphiphiles were assembled to micelles, were found nontoxic and successfully loaded with the chemotherapeutic doxorubicin.

    2. Micron-sized polystyrene particles by surfactant-free emulsion polymerization in air: Synthesis and mechanism (pages 3997–4002)

      Andrew M. Telford, Binh T. T. Pham, Chiara Neto and Brian S. Hawkett

      Article first published online: 10 JUL 2013 | DOI: 10.1002/pola.26841

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      In this study, a novel, robust approach is presented to produce micrometer-scale-sized polystyrene particles with narrow size distribution in highly concentrated latexes. The approach could be easily employed by those not skilled in the art to produce large quantities of polymer particles for research applications. A recent hypothesis is corroborated for the mechanism of particle growth in surfactant-free emulsion polymerization, based on heterocoagulation of precursor particles onto mature ones.

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    1. Synthesis of polymethacrylamides having a sugar moiety with an aliphatic hydrocarbon spacer and their application to control adhesion of hepatocytes cancer cells on the materials (pages 4003–4010)

      Masayuki Toyoshima, Kozo Matsumoto, Mitsuaki Goto and Takeshi Endo

      Article first published online: 17 JUL 2013 | DOI: 10.1002/pola.26818

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      Methacrylamides having a sugar moiety with an aliphatic hydrocarbon spacer were prepared by two step amidation of a spacer diamine, first with a sugar lactone and then with a methacrylic anhydride. These monomers were radically polymerized in aqueous media using 4,4'-azobis(4-cyanovaleric acid) (ACVA) as radical initiator to give the corresponding polymethacrylamide and their cell (human liver cancer cell (WRL)) adhesion properties were examined.

      In the result, WRL interacted with polymers having a lactose structure with a hexamethylene or 1,4-cyclohexylene spacer by a specific manner and was promoted typical spheroid formation.

    2. The solution phase characterization of poly(ferrocenyldimethylsilane)s by small-angle neutron scattering (pages 4011–4020)

      George R. Whittell, Joe B. Gilroy, Isabelle Grillo, Ian Manners and Robert M. Richardson

      Article first published online: 4 JUL 2013 | DOI: 10.1002/pola.26819

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      Small-angle neutron scattering (SANS) has been used to determine Mw, 〈Rgz and, most notably, Mw/Mn for a series of metallopolymers in solution, and the results evaluated by comparison with those obtained by gel permeation chromatography (GPC). Agreement between the two methods was acceptable, suggesting that SANS would be appropriate for the characterization of other polymer systems, which like some metal-containing examples are not amenable to study by traditional methods.

    3. Design and property of thermoresponsive core–shell fluorescent nanoparticles via RAFT polymerization and suzuki coupling reaction (pages 4021–4030)

      Zeyong Xing, Jian Zhang, Xiaohong Li, Wei Zhang, Laibing Wang, Nianchen Zhou and Xiulin Zhu

      Article first published online: 26 JUN 2013 | DOI: 10.1002/pola.26822

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      The well-defined block copolymer poly(DBCzMA-b-NIPAM) was successfully prepared via RAFT technique. Then the crosslinked core–shell fluorescent nanoparticles were obtained by Suzuki coupling reaction. The obtained core–shell fluorescent nanoparticles showed good thermoresponsive property, which is confirmed by dynamic light scattering observation.

    4. A novel generation of photoactive comb-shaped polyamides for the photoalignment of liquid crystals (pages 4031–4041)

      Alexander Ryabchun, Alexey Bobrovsky, Sung-Ho Chun and Valery Shibaev

      Article first published online: 4 JUL 2013 | DOI: 10.1002/pola.26831

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      A new method of polyamide with photoactive side groups synthesis by means of chemical modification of poly(succinimide) was developed. Azobenzene, cinnamate, and coumarine derivatives were used as side groups. It was revealed that the illumination of those polymer coatings with polarized UV light brings to uniaxial alignment of low-molar-mass liquid crystals deposited on them. The obtained polyamides can be used as photoalignment materials.

    5. Quantification of ATRP initiator density on polymer latex particles by fluorescence labeling technique using copper-catalyzed azide-alkyne cycloaddition (pages 4042–4051)

      Masakatsu Kasuya, Tatsuo Taniguchi, Ryuhei Motokawa, Michinari Kohri, Keiki Kishikawa and Takayuki Nakahira

      Article first published online: 28 JUN 2013 | DOI: 10.1002/pola.26800

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      We developed a novel fluorescence labeling technique for quantification of surface densities of atom transfer radical polymerization (ATRP) initiators on polymer particles. ATRP initiators on the surface of polymer particles were converted into azide groups with sodium azide, followed by fluorescent labeling with alkyne-modified dansyl via copper-catalyzed azide-alkyne cycloaddition. The surface initiator densities on polymer particles calculated gave close agreement with those obtained by a conductometric titration technique.

    6. Synthesis, characterization, and evaluation of novel polyhydantoins as gas separation membranes (pages 4052–4060)

      Rubén Tejero, Ángel E. Lozano, Cristina Álvarez and Javier de Abajo

      Article first published online: 23 JUL 2013 | DOI: 10.1002/pola.26806

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      Novel polyhydantoins (PHYs) were synthetized by the polycondensation of newly synthesized aromatic diisocyanates and bisiminoacetates following a two-step polycondensation route which involved the acid-catalyzed cyclization of intermediate polyureas. Soluble PHYs were attained in high yield and high molecular weight. They showed high Tg and high thermal resistance along with remarkable mechanical strength. PHYs were evaluated for the first time as gas separation membranes and they exhibited promising gas separation properties.

    7. Synthesis and characterization of fused-thiophene containing naphthalene diimide n-type copolymers for organic thin film transistor and all-polymer solar cell applications (pages 4061–4069)

      Mingjian Yuan, Matthew M. Durban, Peter D. Kazarinoff, David F. Zeigler, Andrew H. Rice, Yukari Segawa and Christine K. Luscombe

      Article first published online: 28 JUN 2013 | DOI: 10.1002/pola.26812

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      N-type NDI-fused-thiophene based copolymers with each copolymer differing in the number of fused thiophenes in the donor monomer is reported. Increasing the number of fused-thiophene moieties within an NDI-copolymer backbone is shown to enable tuning of the electronic structure. Electron mobilities and on/off ratios as high as 0.012 cm2V-1s-1 and Ion/Ioff >105 were measured from n-channel thin-film transistors fabricated using NDI-xfTh copolymers. Preliminary all-polymer organic photovoltaic performances are presented.

    8. A helical chiral polymer-based chromo-fluorescence and CD response sensor for selective detection of trivalent cations (pages 4070–4075)

      Lu Wang, Fei Li, Xunhua Liu, Guo Wei, Yixiang Cheng and Chengjian Zhu

      Article first published online: 28 JUN 2013 | DOI: 10.1002/pola.26813

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      A novel BINAM-based helical chiral polymer was developed, which exhibited remarkable “turn-on” fluorescence enhancement response toward trivalent metal cations (M3+, M = Al, Cr, Fe) over mono- and divalent metal cations. The solution of the polymer turns on bright blue fluorescence color upon the addition of trivalent metal cations under a commercially available UV lamp, this change can be clearly observed by the naked eyes for direct visual discrimination at low concentration.

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    1. Minute amounts of organically modified montmorillonite improve the properties of polyisobutylene-based polyurethanes (pages 4076–4087)

      Nihan Nugay, Turgut Nugay and Joseph P. Kennedy

      Article first published online: 26 JUN 2013 | DOI: 10.1002/pola.26814

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      We discovered that polyisobutylene (PIB)-based polyurethanes (PIB-PUs) containing 0.5% organically modified montmorillonite (OmMMT) surprisingly produce clear films exhibiting greatly improved tensile strength, elongation, toughness, creep, and stress relaxation relative to those of unmodified PU. The OmMMT was prepared by reacting sodium montmorillonite with N+Me3CH2CH2CH2NH2. The findings, including extensive characterization results, were discussed and explained in terms of a novel nanocomposite morphology.

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    1. Preparation of polyacrylonitrile via SET-LRP catalyzed by lanthanum powder in the presence of VC (pages 4088–4094)

      Zhihai Hao, Jiang Zhang, Hou Chen, Delong Liu, Dongju Wang, Huanying Qu and Jimei Lang

      Article first published online: 28 JUN 2013 | DOI: 10.1002/pola.26815

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      A novel catalyst system based on La(0)/hexamethylenetetramine complexes is used for single electron transfer-living radical polymerization (SET-LRP) of acrylonitrile (AN) in the presence of ascorbic acid (VC) with carbon tetrachloride (CCl4) as a initiator and N,N-dimethylformamide (DMF) as a solvent. Compared with SET-LRP of AN in the absence of VC, monomer conversion is markedly increased. SET-LRP of AN in the presence of VC is also conducted in the presence of air. The kinetic studies show that the polymerizations both in the absence of oxygen and in the presence of air proceed in a well-controlled manner. With the respect to the polymerization in the absence of oxygen, the polymerization in the presence of air provides slower reaction rate and broader polydispersity under the same experimental conditions.

    2. Titanium complexes bearing carbamato ligands as catalytic precursors for propylene polymerization reactions (pages 4095–4102)

      Mohammad Hayatifar, Claudia Forte, Guido Pampaloni, Yury V. Kissin, Anna Maria Raspolli Galletti and Stefano Zacchini

      Article first published online: 1 JUL 2013 | DOI: 10.1002/pola.26816

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      N,N-Dialkylcarbamato complexes of titanium(IV) in combination with MAO or AlMe3-depleted MAO in chlorobenzene, are highly active in polymerization of propylene and produce mostly atactic polypropylene. Replacement of chlorobenzene with toluene leads to a lower catalyst activity but produces partially isotactic polypropylene.

    3. Reduced-bandgap triphenylamine-alt-benzo[1,2-b:4,5-b′]dithiophene copolymers pending benzothiadiazole or diketopyrrolopyrrole units for efficient polymer solar cells (pages 4103–4110)

      Kaixuan Nie, Hua Tan, Xianping Deng, Yafei Wang, Qing Chen, Ying Huang, Yu Liu, Chuncheng Yang, Zhenrong Huang, Meixiang Zhu and Weiguo Zhu

      Article first published online: 2 JUL 2013 | DOI: 10.1002/pola.26817

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      Two new side-chain donor-acceptor (D-A)-based triphenylamine-alt-benzo[1,2-b:4,5-b′]dithiophene copolymers (P1 and P2) with pendant benzothiadiazole or diketo-pyrrolopyrrole in triphenylamine unit were obtained. The maximum power conversion efficiency of 3.17% with a highest open-circuit voltage of 0.86 V and a maximum short-circuit current of 10.77 mA cm−2 was observed in their bulk heterojunction polymer solar cells using PC71BM as acceptor under an illumination of AM 1.5, 100 mW cm−2. Our work indicated that pending the A unit onto one of the alternating binary D units in the main chain can greatly improve the photovoltaic properties for its resulting side-chain D-A-based copolymers.

    4. Cationic ring-opening polymerization of novel 1,3-dehydroadamantanes with various alkyl substituents: Synthesis of thermally stable poly(1,3-adamantane)s (pages 4111–4124)

      Sotaro Inomata, Yusuke Harada, Yuya Nakamura, Yosuke Uehara and Takashi Ishizone

      Article first published online: 3 JUL 2013 | DOI: 10.1002/pola.26820

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      Ring-opening polymerizations of novel 1,3-dehydroadamantanes with various alkyl substituents, such as ethyl, butyl, hexyl, octyl, and isobutyl groups, proceeded to afford corresponding poly(1,3-adamantane)s in high yields under cationic or radical conditions. Resulting polymers showed excellent solubility toward common organic solvents due to introduction of flexible alkyl substituents and asymmetrical structures in repeating units. Weight loss temperatures (10%) of polymers were observed over 400 °C, indicating high thermal stability.

    5. Single-step synthesis of internally functionalizable hyperbranched polyethers (pages 4125–4135)

      Raj Kumar Roy and S. Ramakrishnan

      Article first published online: 3 JUL 2013 | DOI: 10.1002/pola.26821

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      A simple methodology to prepare internally clickable hyperbranched polyethers carrying hydrophobic decyl chains at the periphery has been presented. Thiol-ene click reaction permits the installation a variety of interesting functional groups within the core.

    6. New quinoxaline derivatives as accepting units in donor–acceptor type low-band gap polymers for organic photovoltaic cells (pages 4136–4149)

      Ji-Hoon Kim, Chang Eun Song, Hee Un Kim, In-Nam Kang, Won Suk Shin, Moo-Jin Park and Do-Hoon Hwang

      Article first published online: 3 JUL 2013 | DOI: 10.1002/pola.26823

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      The novel electron-accepting quinoxaline derivative monomers, 5,8-dibromoquinoxaline (Qx), 8,11-dibromobenzo[a]phenazine (BPz), 10,13-dibromodibenzo[a,c]phenazine (DBPz), and 8,11-dibromo-5-(9H-carbazol-9-yl)benzo[a]phenazine) (CBPz), were synthesized and copolymerized with electron donating monomers such as benzo[1,2-b:4,5-b′]dithiophene (BDT) through Stille cross-coupling polymerization. Bulk hetero-junction photovoltaic devices were fabricated and characterized using the synthesized polymers as electron donors and [6,6]-phenyl C71-butyric acid methyl ester (PC71BM) as electron acceptor.

    7. Highly efficient quenching of nanoparticles for the detection of electron-deficient nitroaromatics (pages 4150–4155)

      Patrick Marks, Sage Cohen and Mindy Levine

      Article first published online: 26 JUN 2013 | DOI: 10.1002/pola.26824

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      The highly efficient fluorescent quenching of organic polymer-derived nanoparticles by DNT and TNT is reported herein. This quenching occurs for both nanoparticles and thin films, but not for well-dissolved polymer solutions, which confirms the necessity of inter-polymer contact for efficient quenching. The quenching is also selective for DNT and TNT over other common small molecules such as nitrobenzene and cyclohexanone. This particle-based fluorescent quenching can lead to substantial applications in the detection of nitroaromatic explosives.

    8. The effect of photocrosslinkable groups on thermal stability of bulk heterojunction solar cells based on donor–acceptor-conjugated polymers (pages 4156–4166)

      Xun Chen, Lie Chen and Yiwang Chen

      Article first published online: 3 JUL 2013 | DOI: 10.1002/pola.26828

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      The different types of photocrosslinkable groups into a low band-gap donor–acceptor conjugated polymer are investigated for the thermal stability of bulk heterojunction solar cells. Compared with vinyl groups, bromine-, and azide-photocrosslinkable groups are more prompt for photocrosslinking to yield a denser crosslinking network. An appropriate crosslinking network results in dramatically enhanced the device thermal stability without sacrificing the performance through maintained homogenous active morphology.

    9. Synthesis and new application of green and recyclable cyclic poly(L-lactide)-clay hybrid (pages 4167–4174)

      Aitha Vishwa Prasad, Algin Oh Biying, Woo Yuan Ling, Ludger Paul Stubbs and Yinghuai Zhu

      Article first published online: 3 JUL 2013 | DOI: 10.1002/pola.26829

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      Green and recyclable cyclic poly(L-lactide)-clay hybrid was synthesized by a zwitterionic ring-opening polymerization catalyzed by in situ generated N-heterocyclic carbene catalyst. Palladium (0) nanoparticles were supported and well dispersed on the hybrid to form the new catalyst nanocomposite. The composite was found to be a highly efficient and recyclable catalyst for aminocarbonylation reaction of aryl halides with various amines.

    10. pH-sensitive polymeric micelles based on amphiphilic polypeptide as smart drug carriers (pages 4175–4182)

      Yi Li, Guang Hui Gao and Doo Sung Lee

      Article first published online: 3 JUL 2013 | DOI: 10.1002/pola.26830

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      A series of pH-sensitive amphiphilic diblock copolymers based on polypeptide were synthesized by ring-opening polymerization using poly(ethylene glycol)-amine as a macroinitiator. These polymers were ionized and soluble at low pH, whereas core/shell-structured micelles were formed from these polymers at pH 7.4. By controlling the conversion of benzyl groups on the side chains of the polymer, the pH-sensitive destabilization of these micelles was precisely controlled. Moreover, these micelles were able to retain doxorubicin at pH 7.4 but rapidly release them at low pH.

    11. Narrowly distributed homotelechelic polymers in 30 minutes: Using fast in situ pre-functionalized ROMP initiators (pages 4183–4190)

      Nils Hanik and Andreas F. M. Kilbinger

      Article first published online: 3 JUL 2013 | DOI: 10.1002/pola.26832

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      Grubbs' 3rd generation ruthenium catalyst shows a strong preference for reaction with strained olefins such as norbornenes over non-strained olefins such as symmetrical acyclic olefins typically employed as chain transfer agents in ROMP. Exploiting these kinetic differences allows the synthesis of narrow polydispersity homo-telechelic polymers in a fast one-pot reaction.

    12. High molecular weight poly(ethylene-2,5-furanoate); critical aspects in synthesis and mechanical property determination (pages 4191–4199)

      Rutger J. I. Knoop, Willem Vogelzang, Jacco van Haveren and Daan S. van Es

      Article first published online: 3 JUL 2013 | DOI: 10.1002/pola.26833

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      The bench scale polymerization of high molecular weight (Mn = 80,000 g mol−1) furan-2,5-dicarboxylic acid (FDCA) based polyesters by an industrially common combination of melt polymerization and subsequent solid state post condensation is described. Furthermore, absolute molecular weight analysis is performed by triple detector size exclusion chromatography. Mechanical properties of amorphous and crystalline material are determined in combination with a detailed crystallization study.

    13. Synthesis of highly reactive polyisobutylenes with exo-olefin terminals via controlled cationic polymerization with H2O/FeCl3/iPrOH initiating system in nonpolar hydrocarbon media (pages 4200–4212)

      An-Ru Guo, Xiao-Jian Yang, Peng-Fei Yan and Yi-Xian Wu

      Article first published online: 3 JUL 2013 | DOI: 10.1002/pola.26834

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      A controlled cationic polymerization of IB with H2O/FeCl3/iPrOH initiating system has been developed for synthesis of highly reactive polyisobutylenes with near 100 mol % of exo-olefin end groups in nonpolar media, especially in the mixed C4 fractions for its simplicity and low costs.

    14. Cationic copolymerization behavior of epoxide and 3-isochromanone (pages 4213–4220)

      Atsushi Sudo, Akane Suzuki and Takeshi Endo

      Article first published online: 3 JUL 2013 | DOI: 10.1002/pola.26835

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      The cationic copolymerization of epoxide and 3-isochromanone (ICM) proceeds in a statistic manner to give the corresponding copolymer with ICM-derived ester linkages that are distributed randomly in the main chain.

    15. Organic–inorganic copolymers with double-decker silsesquioxane in the main chains by polymerization via click chemistry (pages 4221–4232)

      Kun Wei, Lei Wang and Sixun Zheng

      Article first published online: 4 JUL 2013 | DOI: 10.1002/pola.26836

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      The synthesis of a series of novel organic–inorganic copolymers with polyhedral oligomeric silsesquioxane (POSS) in the main chains is reported by polymerization via the copper-catalyzed Huisgen 1,3-dipolar cycloaddition. These organic–inorganic copolymers are highly rigid and display extremely high thermal stability. Contact angle measurements show that the copolymers are highly hydrophobic and possess very low surface energy.

    16. Synthetic pathway to functional block copolymers with pendent triphenylamine and ethynylpyridine: Effect of countercation on anionic polymerization behavior (pages 4233–4239)

      Beom-Goo Kang, Yong-Guen Yu, Nam-Goo Kang and Jae-Suk Lee

      Article first published online: 6 JUL 2013 | DOI: 10.1002/pola.26837

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      Potassium tert-butoxide (KOBut) significantly affects the synthesis of the well-defined diblock copolymer containing pendent triphenylamine and ethynylpyridine when sec-butyllithium (s-BuLi) is used as an initiator. The precisely controlled polymer can be synthesized by using excess KOBut due to the change in the countercation from Li+ to K+ and the suppression of ion dissociation by the salt common effect.

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