Journal of Polymer Science Part A: Polymer Chemistry

Cover image for Vol. 52 Issue 2

15 January 2014

Volume 52, Issue 2

Pages i–iv, 149–294

  1. Cover Image

    1. Top of page
    2. Cover Image
    3. Rapid Communication
    4. Articles
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      Cover Image, Volume 52, Issue 2 (pages i–ii)

      Article first published online: 7 DEC 2013 | DOI: 10.1002/pola.27039

      Thumbnail image of graphical abstract

      The schematic image represents the synthesis of a range of linear degradable poly(β-thioester)s (PBTs) via hexylamine-catalyzed thiol-ene Michael additions between various diacrylate and dithiol monomers. As presented by Thomas Junkers et al. on page 178, PBTs with molar masses up to 12000 g·mol-1 are obtained. Polar PBTs are synthesized based on ethylene glycol-containing monomers in benign media. Furthermore, urethane containing PBTs are obtained without direct use of isocyanates during polymerization. Also, polystyrene oligomers synthesized via a bifunctional trithiocarbonate RAFT agent are reacted with diacrylates, likewise allowing for PBT synthesis and thus creating degradable polystyrene copolymers. Finally, by tuning the stoichiometric monomer ratio, alkyne end group functionalities are introduced into a PBT, giving access to modular polymer design strategies.

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      Cover Image, Volume 52, Issue 2 (pages iii–iv)

      Article first published online: 7 DEC 2013 | DOI: 10.1002/pola.27040

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      The cover image shows a schematic structure of a polypeptide ionic liquid (PIL) with a helical polypeptide main-chain and N-butyl imidazolium side-chains, as presented by Qin Hu, Yong Deng, Qiulin Yuan, Ying Ling, and Haoyu Tang on page 149. A series of helical PILs with different main-chain lengths has been synthesized via ring-opening polymerization and alkyne–azide 1,3-dipolar cycloaddition. They showed superior single-walled carbon nanotube (SWCNT) dispersibility in water.

  2. Rapid Communication

    1. Top of page
    2. Cover Image
    3. Rapid Communication
    4. Articles
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      Polypeptide ionic liquid: Synthesis, characterization, and application in single-walled carbon nanotube dispersion (pages 149–153)

      Qin Hu, Yong Deng, Qiulin Yuan, Ying Ling and Haoyu Tang

      Article first published online: 11 NOV 2013 | DOI: 10.1002/pola.26991

      Thumbnail image of graphical abstract

      Polypeptide ionic liquids with a helical polypeptide main-chain and N-butyl imidazolium side chains have been synthesized via copper-mediated [2+3] alkyne–azide 1,3-dipolar cycloaddition. They showed superior single-walled carbon nanotube (SWCNT) dispersibility in water (up to 1045.8 mg L-1) depending on the polymer-to-SWCNT weight ratios and polypeptide main-chain lengths.

  3. Articles

    1. Top of page
    2. Cover Image
    3. Rapid Communication
    4. Articles
    1. Spotlight Article

      Conjugated block copolymers via functionalized initiators and click chemistry (pages 154–163)

      Kendall A. Smith, Deanna L. Pickel, Kevin Yager, Kim Kisslinger and Rafael Verduzco

      Article first published online: 6 NOV 2013 | DOI: 10.1002/pola.26984

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      All-conjugated block copolymers contain two π-conjugated, semiconductive polymer blocks and are of interest for organic electronic applications, such as organic photovoltaics. A series of all-conjugated block copolymers is prepared here through click chemistry. Crystallization of one or both polymer blocks is predominant in the thin-film structure, and the preferred orientation of the crystallites can be directed by varying processing and annealing conditions.

    2. Partially renewable copolyesters prepared from acetalized d-glucitol by solid-state modification of poly(butylene terephthalate) (pages 164–177)

      Erik Gubbels, Cristina Lavilla, Antxon Martínez de Ilarduya, Bart A. J. Noordover, Cor E. Koning and Sebastián Muñoz-Guerra

      Article first published online: 6 NOV 2013 | DOI: 10.1002/pola.26985

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      The nonsymmetrical bicyclic D-glucose-derived diol 2,4:3,5-di-O-methylene-D-glucitol (Glux) was successfully introduced into the poly(butylene terephthalate) (PBT) backbone using the solid-state modification (SSM) technique, yielding partially biobased copolyesters with a non-random chemical microstructure. Due to both the inherently rigid structure of Glux and the relatively slow randomization of the Glux-based copolyesters in the melt, these materials showed extraordinary properties, such as higher melting points and glass transition temperatures compared with other sugar-based copolyesters prepared by SSM.

    3. Spotlight Article

      Facile design of degradable poly(β-thioester)s with tunable structure and functionality (pages 178–187)

      Neomy Zaquen, Benjamin Wenn, Kayte Ranieri, Joke Vandenbergh and Thomas Junkers

      Article first published online: 6 NOV 2013 | DOI: 10.1002/pola.26986

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      A range of linear degradable poly(β-thioesters) (PBTs) are synthesized via hexylamine catalyzed thiol–ene Micheal additions between diacrylates and dithiol monomers. Also, polystyrene oligomers synthesized via a bifunctional trithiocarbonate reversible addition fragmentation transfer agent are reacted with diacrylates, likewise allowing for PBT synthesis. By tuning the stoichiometric monomer ratio in the polymerization, end group functional PBTs are also accessible.

    4. Synthesis and pH-responsive assembly of methoxy poly(ethylene glycol)-b-poly(ε-caprolactone) with pendant carboxyl groups (pages 188–199)

      Yan Zhang, Jinhong Li, Zhengzhen Du and Meidong Lang

      Article first published online: 11 NOV 2013 | DOI: 10.1002/pola.26987

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      The water-soluble copolymer methoxy poly(ethylene glycol)-b-poly(ε-caprolactone) bearing pendant carboxyl groups was prepared based on the new benzyloxycarbonylmethyl-functionalized ε-caprolactone monomers. The copolymers self-assembled by pH induction, and existed as unimers, micelles, or large aggregates in a different pH environment due to the counteraction between the hydrophobic interaction from poly-(ε-caprolactone) (PCL) and the ionization of the carboxyl groups along the polymer chain. Therefore, carboxyl group-functionalized mPEG-b-PCL may be a promising candidate as a pH-sensitive drug carrier.

    5. Poly(ether ketone)s bearing pendent sulfonate groups via copolyacylation of a sulfonated monomer and isomeric AB-type comonomers (pages 200–207)

      Zhenghui Zhang and Tongwen Xu

      Article first published online: 6 NOV 2013 | DOI: 10.1002/pola.26988

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      Poly(ether ketone)s bearing pendent sulfonate groups (SPEK-x/y/z) are prepared by copolymerizing two isomeric AB-type self-condensable comonomers (i.e., 4-phenoxybenzoic acid (p-POBA) and 3-phenoxybenzoic acid (m-POBA)) with a presulfonated monomer SBP. It is found that p-POBA is much better than m-POBA with respect to basic properties of corresponding proton exchange membranes. SPEK-x/y/z membranes, optimized by tuning the contents of sulfonate groups, show potential application in fuel cells.

    6. Benzodithiophene-based poly(aryleneethynylene)s: Synthesis, optical properties, and applications in organic solar cells (pages 208–215)

      Shuguang Wen, Xichang Bao, Wenfei Shen, Chuantao Gu, Zhengkun Du, Liangliang Han, Dangqiang Zhu and Renqiang Yang

      Article first published online: 11 NOV 2013 | DOI: 10.1002/pola.26989

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      Introducing the benzo[1,2-b:4,5-b′]dithiophene unit through the benzene ring to construct poly(aryleneethynylene)s, two types of conjugated polymers are synthesized and characterized. The polymers show an intense interchain interaction and deep HOMO levels of ≤-5.5 eV. The photovoltaic performance is investigated by fabricating the BHJ solar cell device; high Voc values (≥0.90 V) and a conversion efficiency of 2.40% are obtained under the illumination of AM1.5G, 100 mW cm-2.

    7. Biobased poly(2,5-furandimethylene succinate-co-butylene succinate) crosslinked by reversible Diels–Alder reaction (pages 216–222)

      Tabito Ikezaki, Reishi Matsuoka, Kenichi Hatanaka and Naoko Yoshie

      Article first published online: 11 NOV 2013 | DOI: 10.1002/pola.26990

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      Biobased copolymers poly(2,5-furandimethylene succinate-co-butylene succinate) were synthesized and crosslinked by means of a reversible Diels-Alder reaction with bis-maleimide. The mechanical properties of the network polymers were controlled by adjustment of the comonomer composition of the parent copolymer and the maleimide-to-furan ratio. Some of the copolymers exhibited healing ability at room temperature, and their healing efficiencies could be enhanced by solvent or heat.

    8. Spotlight Article

      Photochemical isomerization of norbornadiene-containing polytriazoles obtained by click chemistry polyaddition (pages 223–231)

      Imen Abdelhedi Miladi, Bhanu Prakash Mudraboyina, Ahmed Oueslati, Eric Drockenmuller and Hatem Ben Romdhane

      Article first published online: 12 NOV 2013 | DOI: 10.1002/pola.26992

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      Two series of polyesters and polyethers containing both norbornadiene and triazole units in the main chain were synthesized by CuAAC polyaddition of dialkynes with various aromatic diazides. The obtained polymers have been characterized by 1H NMR, SEC, TGA, and DSC analyses. The photochemical isomerization of the norbornadiene residues into quadricyclanes was investigated by UV–vis spectroscopy from polymer films and confirmed by 1H NMR spectroscopy in DMSO-d6 solution.

    9. Perfluorocyclohexenyl aryl ether polymers via polycondensation of decafluorocyclohexene with bisphenols (pages 232–238)

      Babloo Sharma, Sarah C. Hill, Shawna M. Liff, William T. Pennington and Dennis W. Smith Jr.

      Article first published online: 26 NOV 2013 | DOI: 10.1002/pola.26995

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      A unique class of semifluorinated perfluorocyclohexenyl (PFCH) aryl ether homopolymers and their copolymers with random and alternating architectures is synthesized via step-growth polycondensation reaction of commercially available bisphenols and decafluorocyclohexene in the presence of a triethylamine. The polymers exhibit tunable thermal properties depending on the functional spacer group (R). These semifluorinated PFCH aromatic ether polymers keep the enchained PFCH olefin moieties intact for further reactions such as crosslinking and application-specific functionalization.

    10. Efficient Cu(I) acetate-catalyzed cycloaddition of multifunctional alkynes and azides: From solution to bulk polymerization (pages 239–247)

      Benedict Sandmann, Bobby Happ, Martin D. Hager, Jürgen Vitz, Erik Rettler, Peter Burtscher, Norbert Moszner and Ulrich S. Schubert

      Article first published online: 17 NOV 2013 | DOI: 10.1002/pola.26996

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      The solvent-free copper-catalyzed alkyne azide 1,3-cycloaddition technique can be used for the preparation of different constructions of polymers. By using multifunctional alkynes and azides it is possible to synthesize materials with notable mechanical properties that make them interesting for different applications.

    11. The behavior of poly(amino acids) containing l-cysteine and their block copolymers with poly(ethylene glycol) on gold surfaces (pages 248–257)

      Rodolphe Obeid, Tracy Armstrong, Xiaoju Peng, Karsten Busse, Jörg Kressler and Carmen Scholz

      Article first published online: 14 NOV 2013 | DOI: 10.1002/pola.26997

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      Block copolymers consisting of poly(ethylene glycol) (PEG) and l-cysteine-containing poly(amino acid)s (PAAs) were synthesized as polymeric multianchor systems for covalent attachment to gold surfaces or surfaces decorated with gold nanoparticles. The image shows PEG-b-poly((l-Glu)50-co-(l-Cys)10) bound selectively to the gold nanoparticles. The phase separation between PEG and PAA is clearly visible and the morphology resembles screw dislocations.

    12. Spotlight Article

      Synthesis of orthogonally addressable block copolymers via reversible addition fragmentation chain transfer polymerization and subsequent chemoselective postmodification (pages 258–266)

      Artur Mardyukov, Matthias Tesch and Armido Studer

      Article first published online: 18 NOV 2013 | DOI: 10.1002/pola.26998

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      Synthesis of bifunctional block copolymers bearing orthogonally reactive backbone substituents, such as hexafluoroisopropyl esters and α-hydroxyalkylphenylketones, as additional photoactive moieties via RAFT polymerization is reported. The photoactive blocks are functionalized through a nitroxide photoclick-trapping reaction; the active esters are thermally amidated using various amines. The process is successfully applied to the synthesis of a small polymer library and also to the preparation of homo and block polynitroxides using 4-amino-TEMPO as the amine component in the transamidation reaction.

    13. Synthesis and thermal, mechanical, and optical properties of A–B–A or A–B block copolymers containing poly(norbornene-co-1-octene) (pages 267–271)

      Ryo Tanaka, Takuya Suenaga, Zhengguo Cai, Yuushou Nakayama and Takeshi Shiono

      Article first published online: 17 NOV 2013 | DOI: 10.1002/pola.26999

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      A–B–A or A–B block copolymers including poly(norbornene-co-1-octene) with atactic polypropylene or poly(methyl methacrylate) segments were first synthesized by using ansa-fluorenylamidotitanium complex as a catalyst. These copolymers were soluble in chloroform, which enabled the preparation of thin films by solution casting at low temperature. With the introduction of the polypropylene block, elongation of the polymer film was greatly improved.

    14. Enhancement of redox stability and electrochromic performance of aromatic polyamides by incorporation of (3,6-dimethoxycarbazol-9-yl)-triphenylamine units (pages 272–286)

      Hui-Min Wang and Sheng-Huei Hsiao

      Article first published online: 25 NOV 2013 | DOI: 10.1002/pola.27001

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      What's new?

      A new series of aromatic polyamides with CzTPA units was synthesized from 4,4′ -diamino-40″-(3,6-dimethoxycarbazol-9-yl)triphenylamine and aromatic dicarboxylic acids. The polyamides display enhanced redox stability and electrochromic performance as compared to the corresponding analogs without methoxy substituents on the active sites of the carbazole unit. The polyamide films show strong color changes from colorless to yellowish green and blue in a low switching time during oxidation, together with enhanced near-infrared absorption, moderate coloration efficiency, and long-term switching stability.

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      Water-soluble, biocompatible polyphosphazenes with controllable and pH-promoted degradation behavior (pages 287–294)

      Sandra Wilfert, Aitziber Iturmendi, Wolfgang Schoefberger, Kushtrim Kryeziu, Petra Heffeter, Walter Berger, Oliver Brüggemann and Ian Teasdale

      Article first published online: 22 NOV 2013 | DOI: 10.1002/pola.27002

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      Hydrophilic graft polyphosphazenes with excellent water solubility and tailored hydrolytic degradability were successfully synthesized. Degradation of these polymers show a pH-promoted response with degradation rates ranging from days to months, relevant for use in the field of aqueous biomedical applications such as polymer drug delivery. Biocompatibility and the benign nature of the polymers and degradation products are confirmed by preliminary cell viability testing.

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