Journal of Polymer Science Part A: Polymer Chemistry

Cover image for Vol. 51 Issue 11

June 2013

Volume 51, Issue 11

Pages i–iv, 2319–2526

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      Cover Image, Volume 51, Issue 11 (pages i–ii)

      Article first published online: 26 APR 2013 | DOI: 10.1002/pola.26709

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      A new carbazole-based electron accepting unit, 5-(2,7-dibromo-9H-carbazol-9-yl)ben-zo[a]phenazine (CBP), is newly synthesized as the acceptor part of donor-acceptor type low band-gap polymers for polymer solar cells, as presented by Ji-Hoon Kim, Hee Un Kim, Chang Eun Song, Moo-Jin Park, In-Nam Kang, Won Suk Shin, and Do-Hoon Hwang on page 2354. The CBP is copolymerized with electron-donating monomers, and produces two alternating copolymers, PBDT-CBP and PBDTT-CBP. An alternating copolymer (PBDT-CBZ) consisting of 9-alkylcarbazole (CBZ) and BDT units is also synthesized for comparison. CBP containing polymers (PBDT-CBP and PBDTT-CBP) show a significantly red-shifted broad absorption between 300 and 850 nm compared with that of PBDT-CBZ. The principle described here could be extended to other types of accepting units toward the design of new photoactive materials.

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      Inside Cover, Volume 51, Issue 11 (pages iii–iv)

      Article first published online: 26 APR 2013 | DOI: 10.1002/pola.26710

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      Well-defined acrylate RAFT polymers and multiblock-copolymers are synthesized in a continuous-flow microreactor. Microreactors allow for fast synthesis of materials with high precision due to inherent advantages with respect to stability of reaction conditions and excellent heat transfer. Using this technique, Joke Vandenbergh, Thales de Moraes Ogawa, and Thomas Junkers carry out highly reproducible and fast polymerizations yielding quantitatively functionalized polyacrylates with various molar masses, as presented on page 2366. Polymers can be used as macroinitiators in subsequent microreactor steps, making block-copolymerizations with different acrylate monomers a possibility. Multiblock copolymers consisting of up to five consecutive acrylate blocks have so far been synthesized, demonstrating the benefits of flow microreactor technology compared to batch procedures.

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      Poly(amidoamine)s: Past, present, and perspectives (pages 2319–2353)

      Paolo Ferruti

      Article first published online: 15 MAR 2013 | DOI: 10.1002/pola.26632

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      Poly(amidoamine)s (PAAs) are a family of versatile biocompatible functional polymers. They present a unique combination of properties and are particularly suited for applications such as heavy metal ion scavengers, antiviral and antimalarial polymers, intracellular protein carriers, DNA and siRNA complexing agents, and nonviral transfection promoters. This review provides a comprehensive and up-to-date survey of the state of the art in PAAs, including a vast library of PAA structures reported in the literature.

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    1. New low band-gap semiconducting polymers consisting of 5-(9H-carbazol-9-yl)benzo[a]phenazine as a new acceptor unit for organic photovoltaic cells (pages 2354–2365)

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

      Article first published online: 22 FEB 2013 | DOI: 10.1002/pola.26614

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      The electron-accepting carbazole monomer, 5-(2,7-dibromo-9H-carbazol-9-yl)benzo[a]-phenazine (CBP), is synthesized and copolymerized with electron-donating monomers such as benzo[1,2-b:4,5-b']dithiophene (BDT) or 4,8-bis(2-octyl-2-thienyl)-benzo[1,2-b:4,5-b']dithiophene (BDTT) through Stille cross-coupling polymerization. Bulk heterojunction photovoltaic devices are fabricated and characterized using the synthesized polymers as electron donors and [6,6]-phenyl C71-butyric acid methyl ester (PC71BM) as the electron acceptor.

    2. Spotlight Article

      Precision synthesis of acrylate multiblock copolymers from consecutive microreactor RAFT polymerizations (pages 2366–2374)

      Joke Vandenbergh, Thales de Moraes Ogawa and Thomas Junkers

      Article first published online: 14 FEB 2013 | DOI: 10.1002/pola.26593

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      Well-defined acrylate reversible addition fragmentation chain transfer (RAFT) polymers and multiblock-copolymers are synthesized in a continuous-flow microreactor. Using this technique, highly reproducible and fast polymerizations yield quantitatively functionalized PnBuA with a molar mass of 2000 g mol-1. This material is employed as a macro-RAFT agent for subsequent block-copolymerizations with different acrylate monomers. A multiblock-copolymer (Mn = 31,000 g mol-1, PDI = 1.46) consisting of 5 consecutive acrylate blocks is synthesized, demonstrating the benefits of flow microreactor technology compared to batch procedures.

    3. A computational approach to the free radical polymerization kinetics of alkyl α-hydroxymethacrylate monomers: A structure–reactivity relationship (pages 2375–2384)

      Mehtap Işık, Özlem Karahan, Duygu Avci and Viktorya Aviyente

      Article first published online: 15 MAR 2013 | DOI: 10.1002/pola.26622

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      A quantitative structure–activity relationship model for the reactivity parameters of 16 alkyl α-hydroxymethacrylate (RHMA) monomers at the B3LYP/6–311G* level is derived. To predict the polymerization kinetics, a multiple regression analysis is adopted. Among the descriptors considered, the ionization energy and the electron affinity of the monomers, the bond order of the carbonyl double bond of the monomer, the resonance stabilization parameter of the monomeric radical, and the Mulliken atomic spin density of C5 of the radical correlate with the experimental rates of photopolymerization.

    4. Electrochemiluminescence biosensor for Ramos cells based on a nanostructured conducting polymer composite material (PICA-MWNTs) (pages 2385–2392)

      Guangming Nie, Zhimin Bai, Wenying Yu and Lin Zhang

      Article first published online: 12 MAR 2013 | DOI: 10.1002/pola.26623

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      A novel nanostructured conducting polymer (PICA-MWNTs) with high electroactivity can be easily prepared by direct electrochemical polymerization of indole-6-carboxylic acid in the presence of MWNTs-COOH without any other supporting electrolytes in one step. A simple CdSe ECL sensor based on PICA-MWNTs is fabricated to detect Burkitt's lymphoma (Ramos). This sensor shows a wide linear range, good selectivity, and reproducibility for sensitive quantification of Ramos cells with a low detection limit of 390 cells mL−1.

    5. Oligonucleotide-mediated aggregation of a cationic conjugated polymer for fluorescent detection of mercury ions in an aqueous medium (pages 2393–2400)

      Na Young Kwon, Geunseok Jang, Jongho Kim, Daigeun Kim and Taek Seung Lee

      Article first published online: 19 MAR 2013 | DOI: 10.1002/pola.26624

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      An oligonucleotide-mediated mercury ion detection method is developed using a cationically charged, water-soluble, conjugated polymer as a sensing platform. An emission color change from blue to green can be obtained upon exposure to mercury ions into the polymer-oligonucleotide complex in an aqueous medium. This system demonstrates a specific fluorescence response to mercury ions even in the presence of other metal cations.

    6. Preparation of thermosensitive, calix[4]arene incorporated P(NIPAM-co-HBCalix) hydrogel as a reusable adsorbent of nickel(II) ions (pages 2401–2408)

      Fanyong Yan, Meng Wang, Donglei Cao, Shanshan Guo and Li Chen

      Article first published online: 15 MAR 2013 | DOI: 10.1002/pola.26625

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      The unique features of P(NIPAM-co-HBCalix) hydrogels as a material for Ni2+ adsorption/desorption and thermo-responsive behavior are investigated. The differences between P(NIPAM-co-HBCalix) and PNIPAM hydrogels, and how these differences can alter their response, are presented. The image shows a schematic representation of the synthesis of hydrogels and the concept of the thermally responsive adsorption/desorption behavior of P(NIPAM-co-HBCalix) hydrogel toward Ni2+ ions.

    7. Syntheses and properties of poly(diethyl vinylphosphonate) initiated by lanthanide tris(borohydride) complexes: Polymerization controllability and mechanism (pages 2409–2415)

      Jing Li, Xufeng Ni, Jun Ling and Zhiquan Shen

      Article first published online: 19 MAR 2013 | DOI: 10.1002/pola.26626

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      Controlled polymerization of diethyl vinylphosphonate (DEVP) is carried out using lanthanide tris(borohydride) complexes, Ln(BH4)3(THF)3, as an initiator. An anionic coordination mechanism of the polymerization is clarified by end group analysis using ESI-MS and NMR spectra. The thermal properties and the thermosensitive behavior of PDEVP are characterized.

    8. Sulfonation of polystyrene: Toward the “ideal” polyelectrolyte (pages 2416–2424)

      Jessica E. Coughlin, Andreas Reisch, Marie Z. Markarian and Joseph B. Schlenoff

      Article first published online: 13 MAR 2013 | DOI: 10.1002/pola.26627

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      The sulfonation of polystyrene powder is carried out with concentrated sulfuric acid and an elevated temperature. Fully sulfonated polystyrene chains are obtained with no chain scission or crosslinking, as observed with size exclusion chromatography, dynamic light scattering, and elemental analysis. Kinetic studies show that particle size, acid concentration, and temperature strongly influence the conversion rate. Perdeuterated poly(styrene sulfonate) is also prepared with D2SO4.

    9. Synthesis and properties of hyperbranched polyimides derived from novel triamine with prolonged chain segments (pages 2425–2437)

      Jie Shen, Ying Zhang, Wenqiu Chen, Wenhao Wang, Zushun Xu, Kelvin W. K. Yeung and Changfeng Yi

      Article first published online: 19 MAR 2013 | DOI: 10.1002/pola.26628

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      A novel pyridine-containing triamine 2,4,6-tris[3-(4-aminophenoxy)phenyl]pyridine with prolonged chain segments, ether linkage, and meta-linked units is synthesized and employed to prepare a series of amine- and anhydride-terminated hyperbranched polyimides (HBPIs). The HBPIs inherit excellent thermal properties and exhibit high solubility and good mechanical properties. These superior properties will be favorable in further research.

    10. Hybrid ionic/covalent polymer networks derived from functional imidazolium ionomers (pages 2438–2444)

      Adam Ozvald, J. Scott Parent and Ralph A. Whitney

      Article first published online: 19 MAR 2013 | DOI: 10.1002/pola.26629

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      The N-alkylation of vinyimidazole with brominated poly(isobutylene-co-isoprene) is used to prepare an elastomeric imidazolium ionomer bearing reactive functionality. Radical oligomerization of pendant vinylimidazolium groups yields a thermoset ionomer comprised of a hybrid network of covalent bonds and ionic aggregates, both of which contribute to material properties.

    11. Spotlight Article

      Cationic cyclopolymerization of divinyl ethers with norbornane-, norbornene-, or adamantane-containing substituents: Synthesis of cyclopoly(divinyl ether)s with bulky rigid side chains leading to high glass transition temperature (pages 2445–2454)

      Kazuhiro Morita, Tamotsu Hashimoto, Michio Urushisaki and Toshikazu Sakaguchi

      Article first published online: 19 MAR 2013 | DOI: 10.1002/pola.26630

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      Divinyl ethers 1, 2, and 3 underwent cationic cyclopolymerization with the HCl/ZnCl2 initiating system to give the corresponding cyclopolymers poly(1), poly(2), and poly(3) with a high degree of cyclization and controlled molecular weights. The cyclopolymers possess a glass transition temperature as high as 176–231 °C and good thermal stability.

    12. Synthesis of block and end-functionalized polyesters by triflimide-catalyzed ring-opening polymerization of ε-caprolactone, 1,5-dioxepan-2-one, and rac-lactide (pages 2455–2463)

      Kosuke Makiguchi, Seiya Kikuchi, Toshifumi Satoh and Toyoji Kakuchi

      Article first published online: 19 MAR 2013 | DOI: 10.1002/pola.26631

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      The catalytic activity of triflimide for the ring-opening polymerization of ɛ-caprolactone, 1,5-dioxepan-2-one, and rac-lactide is revealed. All the polymerizations proceed through a controlled/living system. End-functionalized polyesters are produced using functional initiators, such as propargyl alcohol, 6-azido-1-hexanol, N-(2-hydroxyethyl)maleimide, 5-hexen-1-ol, and 2-hydroxyethyl methacrylate. Block copolymerization succeeds by the use of methoxy poly(ethylene glycol) as the macroinitiator, the sequential addition of δ-valerolactone and ɛ-caprolactone, and the click reaction of poly(ɛ-caprolactone) and poly(rac-lactide).

    13. Copolyesters of isosorbide, succinic acid, and isophthalic acid: Biodegradable, high Tg engineering plastics (pages 2464–2471)

      Saber Chatti, Steffen M. Weidner, Aurelie Fildier and Hans R. Kricheldorf

      Article first published online: 13 MAR 2013 | DOI: 10.1002/pola.26635

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      This work deals with the synthesis and characterization of a new class of copolyesters derived from isosorbide, which combines three useful properties: the use of monomers based on renewable resources, biodegradability, and high glass-transition temperatures (Tg), which show a linear dependence on the composition. Large fractions of cyclic copolymers, evidenced by MALDI-TOF mass spectrometry, are characteristic for the optimization of the reaction conditions.

    14. Spotlight Article

      Noncovalent linkage of telechelic oligo(dimethylsiloxanes) via end group attachment of host-cyclodextrins and guest-adamantanes or guest-ferrocenes (pages 2472–2482)

      Berit Knudsen, Beate E. Kergl, Helene Paulsen, Valerij Durnev and Helmut Ritter

      Article first published online: 13 MAR 2013 | DOI: 10.1002/pola.26636

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      The linking of adamantyl, ferrocenyl-, and cyclodextrin-terminated di- and polydimethylsiloxanes via host–guest interactions is presented. The molecules form complexes and lead to novel supramolecular formations of siloxanes. The noncovalent interactions of the functionalized siloxane blocks can be detected in the 1H nuclear magnetic resonance spectra by a chemical shift of the characteristic guest molecule signals. The derivatives show different morphologies in the scanning electron microscopy images. The red-ox behavior of the ferrocenyl-siloxanes and their complexes with the cyclodextrin-siloxanes are studied by cyclovoltammetry.

    15. Epoxy functionalized polymethacrylates based on various multifunctional d-glucopyranoside acetals (pages 2483–2494)

      Dorota Neugebauer, Anna Mielańczyk, Sylwia Waśkiewicz and Tadeusz Biela

      Article first published online: 13 MAR 2013 | DOI: 10.1002/pola.26642

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      The bromoester functionalized d-glucopyranoside acetals based on methyl α-d-glucopyranoside (MeαdGlu) or 2-(hydroxymethyl)phenyl-β-d-glucopyranoside (salicin) are prepared and used to initiate the controlled atom transfer radical copolymerization of glycidyl and methyl methacrylates in the presence of CuCl/dNbpy in anisole at 30 °C. The well-defined copolymers with sugar cores sheltered by two-, three-, four-, or six-polymethacrylate segments with various polymerization degrees (DParm = 15–70) and low dispersity indices (Ð = 1.15–1.30) are successfully synthesized.

    16. Synthesis and characterization of tridentate [ON(H)X] titanium complexes and their applications in olefin polymerization (pages 2495–2503)

      Da-Wei Wan, Zhou Chen, Yan-Shan Gao, Qi Shen, Xiu-Li Sun and Yong Tang

      Article first published online: 13 MAR 2013 | DOI: 10.1002/pola.26643

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      The (arylamino)methylene phenolate titanium (IV) complexes are thermally stable and active to promote ethylene polymerization and copolymerization with 1-alkenes at a high temperature (up to 150 °C). 1-Octene and 1-octadencene are suitable comonomers. The highest activity is 1.89 × 106 g/mol·Ti·h·atm. The introduction of the pendant PPh2 group is important to the catalytic behaviors of the complexes.

    17. Limitations of cyclodextrin-mediated RAFT homopolymerization and block copolymer formation (pages 2504–2517)

      Martin Hetzer, Bernhard V. K. J. Schmidt, Christopher Barner-Kowollik and Helmut Ritter

      Article first published online: 13 MAR 2013 | DOI: 10.1002/pola.26644

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      The limitations of the aqueous cyclodextrin mediated reversible addition fragmentation chain transfer (RAFT) polymerization of the new hydrophobic monomer 4-(tert-butyl)phenyl 6-acrylamidohexanoate (TBP-AA-HO) are investigated. The results obtained by homopolymerization of TBP-AA-HO and chain extension experiments with hydrophilic macro-chain transfer agents indicate a crucial influence of cyclodextrin molecules on the growing polymer chain. A hypothesis is provided that explains the observed limitation of the polymerization process and the achieved low molecular weights for higher monomer/chain transfer agent ratios.

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    3. Highlight
    4. Articles
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      Pd-nanoparticles stabilized by pyridine-functionalized poly(ethylene glycol) as catalyst for the aerobic oxidation of α,β-unsaturated alcohols in water (pages 2518–2526)

      Guido Giachi, Werner Oberhauser, Marco Frediani, Elisa Passaglia, Laura Capozzoli and Luca Rosi

      Article first published online: 13 MAR 2013 | DOI: 10.1002/pola.26645

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      The reduction of a bis-cationic Pd(II) complex bearing functionalized poly(ethylene glycol) brings about the formation of Pd-nanoparticles of 6.33 ±1.40 nm, which are a stable and recyclable catalyst for the aerobic oxidation of α,β-unsaturated alcohols.

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