Journal of Polymer Science Part A: Polymer Chemistry

Cover image for Vol. 47 Issue 7

1 April 2009

Volume 47, Issue 7

Pages 1731–1970

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      Chiral polymers for resolution of enantiomers (pages 1731–1739)

      Yoshio Okamoto

      Version of Record online: 24 FEB 2009 | DOI: 10.1002/pola.23215

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      Formation of one-handed helical poly(triphenylmethyl methacrylate) (PTrMA) was found through the helix-sense-selective polymerization of methacrylate using chiral anionic initiators, and the existence of a stable helical polymer without chiral side chains was proved. The chiral polymer exhibited unexpected high chiral recognition of various racemic compounds when used as chiral packing material (CPM) for HPLC. This success encouraged us to develop further useful CPMs based on polysaccharides, cellulose, and amylose. By using these polysaccharide-based CPMs, particularly phenylcarbamate derivatives, nearly 90% of chiral compounds can be resolved not only analytically but also preparatively, and several chiral drugs have been produced using the CPMs.

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    1. Synthesis and characterization of novel electroactive polyamides and polyimides with bulky 4-(1-adamantoxy)triphenylamine moieties (pages 1740–1755)

      Yi-Chun Kung, Guey-Sheng Liou and Sheng-Huei Hsiao

      Version of Record online: 24 FEB 2009 | DOI: 10.1002/pola.23264

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      Two series of novel electroactive polyamides and polyimides with adamantoxy-TPA moieties have been prepared from the polycondensation reactions of a newly synthesized diamine monomer, 4-(1-adamantoxy)-4′,4″-diaminotriphenylamine, with various aromatic dicarboxylic acids and dianhydrides, respectively. All the polymers could form morphologically stable and uniform amorphous films using solution-casting techniques. In addition to high Tg and Ts values, high thermal stability and good mechanical properties, the polymers also revealed stable redox and electrochromic characteristics with color change from colorless or pale yellow neutral state to dark blue or bluish green oxidized state. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    2. Highly soluble fluorinated polyimides based on an asymmetric bis(ether amine): 1,7-bis(4-amino-2-trifluoromethylphenoxy)naphthalene (pages 1756–1770)

      Cheng-Lin Chung, Wen-Fu Lee, Chun-Hung Lin and Sheng-Huei Hsiao

      Version of Record online: 24 FEB 2009 | DOI: 10.1002/pola.23269

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      A new trifluoromethyl-substituted bis(ether amine) with an asymmetric molecular structure, 1,7-bis(4-amino-2-trifluoromethylphenoxy)naphthalene, was successfully synthesized from available reagents. A series of fluorinated polyimides with moderate to high molecular weights were synthesized from the newly synthesized bis(ether amine) with various dianhydrides by a conventional two-step polymerization technique. The polyimides exhibited high solubility in many organic solvents and could afford flexible and tough films. They also showed high thermal stability, high optical transparency, and low dielectric constants. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    3. AGET ATRP in water and inverse miniemulsion: A facile route for preparation of high-molecular-weight biocompatible brush-like polymers (pages 1771–1781)

      Jung Kwon Oh, Fabien Perineau, Bernadette Charleux and Krzysztof Matyjaszewski

      Version of Record online: 24 FEB 2009 | DOI: 10.1002/pola.23272

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      Activators generated by electron transfer for atom transfer radical polymerization (AGET ATRP) of oligo(ethylene glycol) monomethyl ether methacrylate (OEOMA) in homogeneous aqueous solution targeting DP = 1000, and in inverse miniemulsion targeting DP = 600, at 30 °C allowed for the preparation of biocompatible, brush-like, high-molecular-weight, water-soluble POEOMA. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    4. Synthesis and characterization of pH sensitive poly(glycidol)-b-poly(4-vinylpyridine) block copolymers (pages 1782–1794)

      Sebastian Mendrek, Aleksandra Mendrek, Hans-Juergen Adler, Andrzej Dworak and Dirk Kuckling

      Version of Record online: 24 FEB 2009 | DOI: 10.1002/pola.23276

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      Block copolymers of poly(glycidol)-b-poly(4-vinylpyridine) with varied PGl/P4VP molar ratio were obtained by ATRP of 4-vinylpyridine initiated by poly(glycidol) macroinitiators. The pH-sensitive properties of the obtained copolymers were studied. DLS measurements showed the formation of stable core-shell aggregates at pH exceeding 4.7. The size of the aggregates and pKa values of copolymers depended significantly upon the PGl/P4VP molar ratio. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    5. Effect of higher nonbenzenoids in optical properties of dihydropyrene–thiophene and dihydropyrene–phenylenevinylene copolymers (pages 1795–1803)

      Yuan Lin and Yee-Hing Lai

      Version of Record online: 24 FEB 2009 | DOI: 10.1002/pola.23279

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      A series of dihydropyrene-based copolymers were synthesized. The core dihydropyrene unit was shown to remain intact in the polymer backbone by 1H NMR studies and the copolymers exhibited higher thermal stability compared with the parent molecule. Extended conjugation effect in the copolymers was evident based on spectroscopic analysis despite a mismatch of macrocyclic dihydropyrene units and small conjugation partners. The copolymers have relatively small band gaps and exhibited blue light emission in photoluminescence studies. Their essentially identical emission spectra suggest that their emission properties were dominated by the dihydropyrene chromophore but independent of the spacer group.

    6. Complex micelles formed from two diblock copolymers for applications in controlled drug release (pages 1804–1810)

      Guiying Li, Lei Guo, Songmei Ma and Junshen Liu

      Version of Record online: 24 FEB 2009 | DOI: 10.1002/pola.23274

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      PtBA-b-PNIPAM and PtBA-b-P4VP coaggregated into core-shell complex micelles in acidic water with the hydrophobic PtBA as the core and soluble PNIPAM/P4VP as the mixed shell. Increasing temperature or pH value, the micelles converted into core-shell-corona structures because of the collapse of PNIPAM or P4VP as the inner shell and soluble P4VP or PNIPAM chains stretching outside as the outer corona. Compared with pure core-shell micelles, release of NAP from complex micelles avoided the burst diffusion and the release rate is more easily controlled by the composition of the mixtures or pH of the medium. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    7. PNIPAM-b-(PEA-g-PDMAEA) double-hydrophilic graft copolymer: Synthesis and its application for preparation of gold nanoparticles in aqueous media (pages 1811–1824)

      Chun Feng, Zhong Shen, Yongjun Li, Lina Gu, Yaqin Zhang, Guolin Lu and Xiaoyu Huang

      Version of Record online: 24 FEB 2009 | DOI: 10.1002/pola.23282

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      A series of well-defined PNIPAM-b-(PEA-g-PDMAEA) double-hydrophilicgraft copolymers were synthesized by the combination of SET-LRP, ATRP, and the grafting-from strategy followed by employing them to prepare stable colloidal gold nanoparticles in aqueous media without any external reducing agent. The morphology and size of the nanoparticles were affected by the length of PDMAEA side chains, pH value, and the feed ratio of the graft copolymer to HAuCl4. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    8. Redox initiated cationic polymerization (pages 1825–1835)

      James V. Crivello

      Version of Record online: 24 FEB 2009 | DOI: 10.1002/pola.23284

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      A novel catalytic method for carrying out the cationic polymerization of epoxide, oxetane, and vinyl monomers has been developed based on a redox initiator system in which the reducing component is delivered to the reaction mixture in the vapor state. The redox couple consists of a diaryliodonium salt that is dissolved in the monomer. A noble metal catalyst is added. The silane reducing agent is introduced to the reaction mixture in the vapor state using air as the carrier gas.

    9. Synthesis and characterization of synthetic polymer colloids colloidally stabilized by cationized starch oligomers (pages 1836–1852)

      Marianne Gaborieau, Hank De bruyn, Siyabonga Mange, Patrice Castignolles, Andreas Brockmeyer and Robert G. Gilbert

      Version of Record online: 24 FEB 2009 | DOI: 10.1002/pola.23287

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      A method is developed for anchoring cationized starch oligomers as electrosteric stabilizers onto synthetic latexes, using Ce4+ to create free-radical grafting sites on the starch. Using α-amylase to randomly cleave starch, and N-isopropyl acrylamide, whose corresponding polymer exhibits a lower critical solution temperature, thermosensitive block oligomers of oligosaccharide and synthetic polymers are synthesized. Above 30 °C, they form self-emulsifying nanoparticles (“frozen micelles”) from which a synthetic latex is grown after addition of methyl methacrylate, the collapsed NIPAM-containing entities functioning as in situ seed. The grafting efficiency is high (as shown by a new 13C solid-state NMR method), and the resulting latex is very colloidally stable. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    10. Synthesis and properties of carbamate- and amine-containing poly(phenylacetylenes) (pages 1853–1863)

      Irfan Saeed, Fareha Zafar Khan, Masashi Shiotsuki and Toshio Masuda

      Version of Record online: 24 FEB 2009 | DOI: 10.1002/pola.23278

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      Novel phenylacetylenes appended with t-Boc- and Fmoc- protected amino functionalities were synthesized, polymerized using [(nbd)RhCl]2 and [(nbd)RhBPh4] catalysts, and poly- (phenylacetylenes) carrying free amino pendants were obtained by deprotection. The presence of t-Boc group in the meta position rendered the polymer capable of being fabricated into free-standing membranes, which displayed good gas permeation characteristics especially high CO2/N2 permselectivity. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    11. Studying the mechanism of thioketone-mediated polymerization via electrospray ionization mass spectrometry (pages 1864–1876)

      Fabian Günzler, Thomas Junkers and Christopher Barner-Kowollik

      Version of Record online: 25 FEB 2009 | DOI: 10.1002/pola.23280

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      The reaction products obtained in thioketone-mediated polymerization of acrylate monomers are mapped via electrospray ionization mass spectrometry. On the basis of the MS data, it can be concluded that the observed control over the polymerization process can be explained by the formation of an equilibrium between propagating radicals and a dormant radical species, which, however, significantly undergoes termination reactions with other radicals, thus limiting the achievable control in the system. All products observed are fully consistent with the proposed reaction mechanism as well as previous results from modeling rate data of the same system. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    12. Synthesis of di- and tri-tertiary amine containing methacrylic monomers and their (co)polymerization via RAFT (pages 1877–1890)

      Bing Yu and Andrew B. Lowe

      Version of Record online: 25 FEB 2009 | DOI: 10.1002/pola.23281

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      The synthesis and RAFT (co)polymerization of three multi-tertiary amine containing methacrylic monomers is described. Homopolymerizations under bulk conditions with 1-methyl-1-cyanoethyl dithiobenzoate at 70 °C proceed in a controlled manner as evidenced by the linear evolution of Mn versus conversion and the low polydispersity indices. M1 and M3 are also demonstrated to readily undergo statistical copolymerization with both hexyl and lauryl methacrylates. Finally, the stimulus responsive aqueous solution behaviors of homopolymers derived from M1 to M3 were determined with an emphasis on the effect of changes in temperature and solution pH. All three homopolymers possessed LCST's spanning the range 22–63 °C and phase separated at elevated pH.

    13. Incorporation of a conjugated side-chain in regioregular polythiophenes: Chiroptical properties and selective oxidation (pages 1891–1900)

      Helmuth Peeters, Thierry Verbiest and Guy Koeckelberghs

      Version of Record online: 25 FEB 2009 | DOI: 10.1002/pola.23283

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      The synthesis, aggregation, and optical properties of a chiral, regioregular, HT-coupled polythiophene, substituted with a conjugated substituent, are studied. The side-chain contributes to the absorption, emission, and redox behavior of the material. Since the consecutive side-chains are, due to the HT-coupling pattern, not in direct conjugation, their electronic properties resemble well those of the monomer and are independent of the conditions. It was also shown that the conjugated side-chain chirally stacks in conditions in which the polymer backbone aggregates but the monomer does not, which demonstrates the ability of conjugated polymers to induce a (chiral) lamellar organization of conjugated moieties, present in their side-chain. Finally, it was shown that the conjugated side-chain can selectively be oxidized, without oxidizing the polythiophene backbone.

    14. Block copolymers of poly(ethylene oxide) and poly(vinyl alcohol) synthesized by the RAFT methodology (pages 1901–1910)

      Yin-Yin Tong, Yong-Quan Dong, Fu-Sheng Du and Zi-Chen Li

      Version of Record online: 25 FEB 2009 | DOI: 10.1002/pola.23288

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      Xanthate end-functionalized poly(ethylene oxide) (PEO) with different molecular weights were synthesized and used as macromolecular chain transfer agents to mediate the radical polymerization of vinyl acetate (VAc). PEO-b-PVAc and PVAc-b-PEO-b-PVAc copolymers were synthesized and hydrolyzed to obtain a series of PEO-b-PVA and PVAc-b-PEO-b-PVA copolymers. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    15. Molecular design, synthesis, and properties of Y-type nonlinear optical polyester containing tricyanovinylthiophene with enhanced thermal stability of second harmonic generation (pages 1911–1919)

      Ga-Young Lee, Jin-Hyang Kim, Hyo Jin No, Ju-Yeon Lee, Bum Ku Rhee and Hee-dok Choi

      Version of Record online: 25 FEB 2009 | DOI: 10.1002/pola.23295

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      We prepared a new Y-type polyester 7 containing 1-(3,4-dioxyethoxy)phenyl)-2-{5-(2,2,3-tricyanovinyl)-2-thiophenyl)}ethenyl groups as pendant NLO-chromophores, which are parts of the polymer backbones. The resulting polymer 7 showed a thermal stability up to 300 °C in TGA thermogram with Tg value from DSC thermogram around 126 °C. The SHG coefficient (d33) of poled polymer film at the 1560 nm fundamental wavelength was near 6.57 × 10−9 esu. The polymer exhibits SHG stability up to Tg and no significant SHG decay was observed below 125 °C. This enhanced thermal stability of optical nonlinearity stemmed from the stabilization of dipole alignment of the NLO-chromophores, which were parts of the polymer main chains.

    16. Synthesis and properties of novel benzimidazole-containing sulfonated polyethersulfones for fuel cell applications (pages 1920–1929)

      Yinghua Qi, Yan Gao, Shuanghong Tian, Antisar R. Hlil, Julie Gaudet, Daniel Guay and Allan S. Hay

      Version of Record online: 25 FEB 2009 | DOI: 10.1002/pola.23298

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      Sulfonated poly(arylene sulfones)s containing 2,6-bis(benzimidazol-2-yl)pyridine (BIP) and sulfonic acid groups have been prepared by copolycondensation of BIP-containing arylene difluoride monomer (DFSBIP) with a sulfonated arylene difluoride (DSDFS) and 4,4′-biphenol (BP). The interaction between BIP and sulfonic acid groups forms ionic cross-linking networks resulting in polymer membranes with good dimensional stability in water, even at high temperature (e.g., 100 °C). IEC of the membranes was investigated through a new simple pH-determination method. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    17. Preparation of comb-like copolymers with amphiphilic poly(ethylene oxide)-b-polystyrene graft chains by combination of “graft from” and “graft onto” strategies (pages 1930–1938)

      Ruiming Sun, Guowei Wang, Chao Liu and Junlian Huang

      Version of Record online: 25 FEB 2009 | DOI: 10.1002/pola.23302

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      The comb-like block copolymers with PS-b-PEO side chains were synthesized for the first time via sequential ROP, ATRP, and ATNRC reaction by “Graft From” and “Graft Onto” strategies. The results confirmed that, in the preparation of copolymers with complicated structure, the ATNRC is a useful and successful method and it would have potential application in polymer chemistry. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    18. End-functionalization of semiconducting species with dendronized terpyridine–Ru(II)–terpyridine complexes (pages 1939–1952)

      Elefterios K. Pefkianakis, Nikolaos P. Tzanetos, Christos L. Chochos, Aikaterini K. Andreopoulou and Joannis K. Kallitsis

      Version of Record online: 25 FEB 2009 | DOI: 10.1002/pola.23289

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      The terpyridine–Ru(II)–terpyridine (tpyRu(II)tpy) coordination chemistry has been utilized for the end-functionalization of various semiconducting species. Semiconducting rigid-rod oligomers (distyrylanthracene, quinquephenylene, mono- and tri-fluorene) were difunctionalized with dendronized tpy–Ru(II)–tpy complexes. Additionally, semiconducting flexible side chain poly(oxadiazole)s, synthesized via atom transfer radical polymerization employing a tpy initiator, were also complexated with a dendronized tpyRu(III)Cl3. These hybrid metal-bearing semiconducting (macro)molecules were characterized for their structural perfection, whereas their optical properties examination showed features arising from both their components. Initial AFM investigation of their thin film morphologies, revealed in some cases, a self-organization tendency in the nanometer scale. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    19. Synthesis and evaluation of new dental monomers with both phosphonic and carboxylic acid functional groups (pages 1953–1965)

      Gorkem Sahin, Aylin Ziylan Albayrak, Zeynep SaraylI Bilgici and Duygu Avci

      Version of Record online: 25 FEB 2009 | DOI: 10.1002/pola.23296

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      New hydrolytically stable, aromatic mono and di(phosphonic) and carboxylic-acid containing monomers were synthesized for use in dental adhesives and composites. The aqueous solutions of monomers 1–3 were acidic, in the range of acidity expected from a mild self-etching dental adhesive monomer. Their interaction with hydroxyapatite was determined by 13C NMR and FTIR techniques. Photo-polymerization of these monomers with the commercial dental monomer, GDMA, showed that reactivity of the monomers was as follows: 1>3>2. Solution polymerization with acrylamide proved the incorporation of the monomers to the polymer matrix.

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      Tandem catalytic system: Rac-Et(ind)2ZrCl2/AlEt2Cl/MAO toward the synthesis of branched polyethylene (pages 1966–1970)

      Wei-Dong Yan, Xiao-Yu Hao, Min Yang, Bin-Yuan Liu and Pan-Ge Liu

      Version of Record online: 25 FEB 2009 | DOI: 10.1002/pola.23285

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      A novel tandem catalytic system, sole catalyst with two different activators, rac-Et(Ind)2ZrCl2/AlEt2Cl/MAO catalytic system is successfully employed to prepare branched polyethylene from ethylene as only monomer in one reactor.

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