Journal of Polymer Science Part A: Polymer Chemistry

Cover image for Vol. 43 Issue 17

1 September 2005

Volume 43, Issue 17

Pages 3719–4015

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      Dendrimer complexes: Fine control of metal assembly in macromolecules (pages 3719–3727)

      Kimihisa Yamamoto

      Version of Record online: 11 JUL 2005 | DOI: 10.1002/pola.20925

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      We show that tin ions (Sn2+) complex to the imine groups of a spherical polyphenylazomethine dendrimer in a stepwise fashion, with complexation in a more peripheral generation proceeding only after complexation in generations closer to the core has been completed. We can control the number and location of metal ions incorporated into dendrimer structures, which might be used as tailored catalysts or building blocks for advanced materials.

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    1. Controlled copolymerization of vinyl acetate with 1-alkenes and their fluoro derivatives by degenerative transfer (pages 3728–3736)

      Sachin Borkar and Ayusman Sen

      Version of Record online: 11 JUL 2005 | DOI: 10.1002/pola.20802

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      The degenerative transfer copolymerization of vinyl acetate with ethene and higher 1-alkenes, as well as their fluoro derivatives (RfCH[DOUBLE BOND]CH2), under mild conditions was carried out using AIBN as the initiator and ethyl iodoacetate as the control agent. The obtained random copolymers were fairly high in alkene content, with high molecular weights and relatively narrow polydispersities. The quasi-living nature of the copolymerization allowed the synthesis of a block terpolymer by sequential addition of two different 1- alkene comonomers to a vinyl acetate copolymerization system. The fluorinated side chains of vinyl acetate/fluoro alkene copolymers segregate toward the air-side of thin films, resulting in advancing water contact angle as high as 114°.

    2. Fluorinated comblike homopolymers: The effect of spacer lengths on surface properties (pages 3737–3747)

      Salima Saïdi, Frédéric Guittard, Claude Guimon and Serge Géribaldi

      Version of Record online: 11 JUL 2005 | DOI: 10.1002/pola.20851

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      A series of polyacrylate monomers with F-alkylalkyl [F(CF2)n(CH2)n] side groups were prepared by free-radical polymerization. The effect of the chemical structure on the surface properties of poly(ethylene terephthalate) was evaluated by variations in the relative length of the fluorocarbon and hydrocarbon units in the side groups. A strong correlation between the bulk organization and surface properties of the polymers was established via X-ray photoelectron spectroscopy and contact-angle measurements. The length of the lateral chain steers this organization: long fluorinated chains and short hydrocarbon spacers are essential elements of the molecular design for such low-surface-energy materials.

    3. Star polymers by ATRP of styrene and acrylates employing multifunctional initiators (pages 3748–3759)

      Katja Jankova, Melania Bednarek and Søren Hvilsted

      Version of Record online: 11 JUL 2005 | DOI: 10.1002/pola.20834

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      Novel tetra-, hexa- and multifunctional macroinitiators are prepared by conversion of ditrimethylolpropane, dipentaerythritol, and poly(3-ethyl-3-hydroxymethyloxetane) to the corresponding 2-bromoisobutyrates or 2-bromopropionates. Star-shaped polystyrene (PS) and polyacrylates based on methyl, n-butyl or n-hexyl acrylate are synthesized with these macroinitiators as cores by atom transfer radical polymerization (ATRP) in a controlled fashion. Hydrolysis of star-PS leads to linear chains having the expected Mn values. Star-PS based on dipentaerythritol are shown to thermally degrade by initial ester scission followed by normal behavior.

    4. Stabilizer-free dispersion copolymerization of maleic anhydride and vinyl acetate. I. Effects of principal factors on microspheres (pages 3760–3770)

      Chang-Min Xing and Wan-Tai Yang

      Version of Record online: 11 JUL 2005 | DOI: 10.1002/pola.20871

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      A novel dispersion copolymerization of maleic anhydride (MAn) and vinyl acetate (VAc) without adding stabilizer is developed, which gives uniform copolymer microspheres with tunable sizes. Only some specific alkyl ester solvents are desirably fit for this unique process. This new type of copolymer microspheres with surface reactive anhydride groups has good solubility in common nontoxic solvents such as water and ethanol. The SEM image is of the polymer microspheres prepared by dispersion copolymerization of MAn and VAc in the absence of stabilizer.

    5. Graft copolymerization of poly(styrene-co-p-choloromethylstyrene) with methyl methacrylate and acryloylmorpholine by atom transfer radical polymerization: Graft copolymer characterization and monomer reactivity ratios (pages 3771–3777)

      Mehmet Mürşi̇t Temüz and Mehmet Coşkun

      Version of Record online: 11 JUL 2005 | DOI: 10.1002/pola.20882

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      In the atom transfer radical graft copolymerization of poly(styrene-co-p-chloromethylstyrene) (62/38) with acryloylmorpholine (1) and methyl methacrylate (2), the monomer reactivity ratios were calculated with the Finemann–Ross (F–R), inverted Finemann–Ross (inverted F–R), Yezrielev–Brokhina–Roskin (Y–B–R), Kelen–Tüdos (K–T), extended Kelen–Tüdos (extended K–T), and Mayo–Lewis (M–L) methods. The Yezrielev–Brokhina–Roskin method gave the best linearity.

    6. Synthesis of core-crosslinked carbosilane block copolymer micelles and their thermal transformation to silicon-based ceramics nanoparticles (pages 3778–3787)

      Kozo Matsumoto and Hideki Matsuoka

      Version of Record online: 11 JUL 2005 | DOI: 10.1002/pola.20879

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      Carbosilane fine particles were synthesized by core-crosslinking of carbosilane block copolymer micelles and they were pyrolytically transformed into silica nanoparticles. The carbosilane block copolymer used here was poly(1-(3-butenyl)-1-methylsilacyclobutane)-block-polystyrene. It formed micelles whose core was composed of polycarbosilane in DMF. The micelle core was cross-linked by hydrosilation with 1,2-bis(dimethylsilylethane). The cross-linked polymer particles were heated under a N2 flow up to 850 °C and gave silica-like nanoparticles.

    7. Copolymerization with the feeding of one of the comonomers: Cationic activated monomer copolymerization of ε-caprolactone with ethylene oxide (pages 3788–3796)

      Melania Bednarek and Przemysław Kubisa

      Version of Record online: 15 JUL 2005 | DOI: 10.1002/pola.20881

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      The cationic copolymerization of ε-caprolactone with ethylene oxide (EO) under the conditions of activated monomer polymerization, that is, with a low-molecular-weight diol as an initiator and BF3 etherate as a catalyst, was studied. The copolymerization was conducted with incremental feeding of the EO comonomer. 1H NMR analysis of samples isolated at different stages of the copolymerization indicated that the average composition of the copolymer was nearly constant over the course of the copolymerization. Matrix-assisted laser desorption/ionization time-of-flight spectra of the products revealed, however, that for the same degree of polymerization, macromolecules containing different numbers of EO units were present. The observed distribution was compared with the simulated one. A good agreement between the observed and simulated spectra was obtained. This indicated that, even when the optimum conditions for the formation of a uniform copolymer were created, the individual macromolecules differed in composition because of the statistical character of the copolymerization.

    8. Synthesis of high molecular weight polystyrene and poly(methyl methacrylate) with low polydispersity by [Cp2ZrCl2] catalyzed aqueous polymerization (pages 3797–3803)

      Braja N. Patra and Manish Bhattacharjee

      Version of Record online: 14 JUL 2005 | DOI: 10.1002/pola.20832

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      Zirconocene dichloride, Cp2ZrCl2, with an anionic surfactant, sodium n-dodecyl sulfate (SDS) as emulsifier has been found to be an effective catalyst for polymerization of monomers like styrene and methylmethacrylate in aqueous medium. The molecular weights of the polymers have been found to be very high with low molecular weight distribution.

    9. Cobalt(II) octanoate and cobalt(II) perfluorooctanoate catalyzed atom transfer radical polymerization of styrene in toluene and fluorous media—A versatile route to catalyst recycling and oligomer formation (pages 3804–3813)

      Marc-Stephan Weiser and Rolf Mülhaupt

      Version of Record online: 18 JUL 2005 | DOI: 10.1002/pola.20873

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      We report a new approach to ATRP, based upon fluorous biphase catalysis using cobalt(II) perfluorooctanoate as catalyst for styrene ATRP and reverse ATRP in the solvent mixture/toluene/cyclohexane/perfluorodecalin (1:1:1 vol %), which are miscible at 90 °C. Upon cooling phase, separation accounted for very effective separation of the perfluoroalkyl-tagged cobalt(II) complex. No residual cobalt was detected in the polymer by means of atom absorption spectroscopy. The very effective recovery is also evidenced by high catalyst activities observed upon recycling of the perfluoroalkyl-tagged cobalt(II) complex in perfluorodecalin.

    10. Synthesis of carbohydrate-segmented polydimethylsiloxanes by hydrosilylation (pages 3814–3822)

      Dirk Henkensmeier, Bors Cajus Abele, Anton Candussio and Joachim Thiem

      Version of Record online: 14 JUL 2005 | DOI: 10.1002/pola.20852

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      In this work, a new route to carbohydrate-segmented polysiloxanes is presented. A series of allyl-group-containing bifunctional carbohydrate derivatives was synthesized and reacted with hydrodimethylsilyl-terminated polysiloxane in hydrosilylation reactions with Speier's catalyst.

    11. Synthesis of methyl methacrylate, styrene, and isobutylene multiblock copolymers using atom transfer and cationic polymerization (pages 3823–3830)

      Luděk Toman, Miroslav Janata, Jiří Spěváček, Petr Vlček, Petra Látalová, Antonín Sikora and Bohumil Masař

      Version of Record online: 15 JUL 2005 | DOI: 10.1002/pola.20884

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      The synthesis of multiblock copolymers of methyl methacrylate (MMA), styrene (S), and isobutylene (IB) by a combination of atom transfer radical polymerization (ATRP) and cationic polymerization is described. First, the poly(S-b-MMA-b-S) triblock copolymer was prepared by ATRP, and then IB was polymerized cationically with the triblock macroinitiator in conjunction with diethylaluminum chloride (Et2AlCl); this gave the poly(IB-b-S-b-MMA-b-S-b-IB) pentablock copolymer.

    12. Systematic parallel investigation of RAFT polymerizations for eight different (meth)acrylates: A basis for the designed synthesis of block and random copolymers (pages 3831–3839)

      Martin W. M. Fijten, Renzo M. Paulus and Ulrich S. Schubert

      Version of Record online: 14 JUL 2005 | DOI: 10.1002/pola.20868

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      The successful polymerized acrylates (right top) and methacrylates (left bottom) via RAFT polymerization using 2-cyano-2-butyl dithiobenzoate as RAFT-agent are displayed.

    13. Unconstrained geometry complexes: Ethylene/α-olefin copolymerizations with a tetramethyldisilyl-bridged Cp-amido titanium complex (pages 3840–3851)

      Joyce Hung and Robert M. Waymouth

      Version of Record online: 14 JUL 2005 | DOI: 10.1002/pola.20862

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      A new disilyl-bridged constrained geometry catalyst analogue, [(N-tert-butylamido)(3-indenyl)tetramethyldisilyl]titanium dichloride, was synthesized and activated with methylaluminoxane (MAO) for the copolymerization of ethylene/propylene and ethylene/1-hexene. Despite the unconstrained nature of the disilyl-bridged catalyst, this catalyst exhibited high comonomer incorporation. The number of regioirregular α-olefin insertions was similar to that observed in polymers made with the monosilyl-bridged constrained geometry catalysts.

    14. Dendronized polymers with tailored surface groups (pages 3852–3867)

      Andreas Nyström and Anders Hult

      Version of Record online: 14 JUL 2005 | DOI: 10.1002/pola.20846

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      To accommodate the need for an understanding of the mechanical properties of dendronized polymers, narrowly distributed materials with comparable degrees of polymerization must be synthesized. In this article a set of dendronized polymers of up to the fourth generation with tailored surface groups have been produced by a combination of atom transfer radical polymerization and divergent growth. The end-groups were altered to achieve hydroxyl, acetate, acetonide, and aliphatic hexadecyl functionalized polymers that all emanate from the same backbone.

    15. Binary copolymerization with full depropagation: A study of methyl methacrylate/α-methyl styrene copolymerization (pages 3868–3877)

      M. J. Leamen, N. T. McManus and A. Penlidis

      Version of Record online: 15 JUL 2005 | DOI: 10.1002/pola.20874

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      The kinetics of the copolymerization of α-methyl styrene (AMS) and methyl methacrylate (MMA) have been revisited for the bulk system. Reactivity ratios and other kinetic parameter estimates based upon a copolymerization model developed by Kruger et al. have been determined for a range of temperatures (60–140 °C). An interesting phenomenon has been uncovered, which shows there is a distinct difference in copolymer composition predicted by the model when compared to experimental data at feed ratios of MMA below a critical value. This deviation also appears to be influenced by the reaction temperature. It is thought that this deviation may be a breakdown of LCA-I. The kinetic parameters follow Arrhenius type behavior while the reactivity ratio for AMS does not show a trend toward zero as previously thought.

    16. Polymeric and colloidal features of latex particles with surface amino groups obtained by semicontinuous seeded cationic emulsion polymerization (pages 3878–3886)

      Jose Ramos and Jacqueline Forcada

      Version of Record online: 14 JUL 2005 | DOI: 10.1002/pola.20828

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      Monodisperse latex particles with different amounts of surface amino and amidine groups were synthesized by means of a semicontinuous seeded cationic emulsion polymerization of styrene and a cationic monomer. High partial overall conversions for styrene and limited ones for the cationic monomer were achieved. A reliable method for the quantification of surface amidine and amino groups was developed. It was found that the amount of surface amidine groups provided by the cationic initiator was higher when the amount of cationic monomer added increased. The value for the partition coefficient of the cationic monomer indicated that this polymerizes with the same probability in the water phase as in the particle. The colloidal stability, in terms of CCC, shows that the latexes would be useful as polymeric supports in immunoassays.

    17. Synthesis, morphology, and viscoelastic properties of cyanate ester/polyhedral oligomeric silsesquioxane nanocomposites (pages 3887–3898)

      Kaiwen Liang, Hossein Toghiani, Guizhi Li and Charles U. Pittman Jr

      Version of Record online: 18 JUL 2005 | DOI: 10.1002/pola.20861

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      Octaaminophenyl(T8)polyhedral oligomeric silsesquioxane (1) was chemically incorporated into thermally cured cyanate ester resins. X-ray diffraction, transmission election microscopy, and IR data were all consistent with the molecular dispersion and chemical bonding of 1 in the continuous cyanate ester network.

    18. Hydrogen-bond-assisted stereocontrol in the radical polymerization of N-isopropylacrylamide with secondary alkyl phosphate: The effect of the bulkiness of the ester group (pages 3899–3908)

      Tomohiro Hirano, Hiroko Kitajima, Satoshi Ishii, Makiko Seno and Tsuneyuki Sato

      Version of Record online: 18 JUL 2005 | DOI: 10.1002/pola.20883

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      The radical polymerization of N-isopropylacrylamide (NIPAAm) with triisopropyl phosphate (TiPP) was investigated. The addition of TiPP induced a syndiotactic specificity that was enhanced by the temperature being lowered. However, almost atactic poly(NIPAAm)s were obtained even by lowering temperature to −80 °C, although the stereospecificity with tri-n-propyl phosphate (TPP) varied from syndiotactic to isotactic with a decrease in temperature. It was revealed that TiPP favored 1:1 complexation at −80 °C, although TPP favored 1:2 complexation. Thus, it was concluded that a slight increase in bulkiness of phosphates influenced the stoichiometry of the NIPAAm-phosphate complex and consequently a drastic change in stereospecificity was observed.

    19. Biodegradable polymers based on renewable resources. IX. Synthesis and degradation behavior of polycarbonates based on 1,4:3,6-dianhydrohexitols and tartaric acid derivatives with pendant functional groups (pages 3909–3919)

      Makito Yokoe, Keigo Aoi and Masahiko Okada

      Version of Record online: 19 JUL 2005 | DOI: 10.1002/pola.20830

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      Novel degradable polycarbonates with pendant functional groups derived from 1,4:3,6-dianhydrohexitols and tartaric acid derivatives were successfully synthesized. Solution polycondensations of 2,5-bis-O-(p-nitrophenoxycarbonyl)hexitols and 2,3-di-O-methyl-L-threitol or 2,3-O-isopropylidene-L-threitol, which are derived from dimethyl L-tartrate or L-tartaric acid, respectively, afforded polycarbonates with pendant methoxy or isopropylidene groups. Sequential acid-catalyzed deprotection of pendant isopropylidene groups gave polycarbonates with pendant hydroxyl groups. The polycarbonates having pendant hydroxyl groups were readily degraded in a phosphate buffer and in an activated sludge.

    20. Arenesulfonyl iodides: The third universal class of functional initiators for the metal-catalyzed living radical polymerization of methacrylates and styrenes (pages 3920–3931)

      Virgil Percec and Cristian Grigoras

      Version of Record online: 19 JUL 2005 | DOI: 10.1002/pola.20860

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      The third class of universal initiators based on arenesulfonyl iodides is reported in this publication. The use of an arenesulfonyl iodide facilitates the synthesis of a polymer containing C[BOND]I, C[BOND]Br, or C[BOND]Cl chain ends with the appropriate catalytic system. A demonstration of the chain-end nature is provided by a combination of 1H NMR, 13C NMR, matrix-assisted laser desorption/ionization time-of-flight, and gel permeation chromatography analytical methods

    21. Synthesis and characterization of novel biodegradable unsaturated poly(ester amide)/poly(ethylene glycol) diacrylate hydrogels (pages 3932–3944)

      Kai Guo and C. C. Chu

      Version of Record online: 21 JUL 2005 | DOI: 10.1002/pola.20781

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      A series of novel biodegradable hydrogels was designed and synthesized from four types of unsaturated poly(ester amide) (UPEA) and poly(ethylene glycol) diacrylate (PEG-DA) precursors by UV photocrosslinking. These newly synthesized biodegradable UPEA/PEG-DA hydrogels were characterized by gel fraction, equilibrium swelling ratio, compressive modulus and interior morphology. The effect of precursors' feed ratio (UPEAs to PEG-DA) on hydrogels' properties was also studied. The incorporation of UPEAs into PEG-DA hydrogels increased their hydrophobicity, crosslinking density and mechanical strength, but reduced Qeq. The differences in hydrogel property were correlated to the chemical structure of the UPEA precursors.

    22. Synthesis of ionic polyurethanes with pyrene rings: Spectral properties and fluorescence quenching study (pages 3945–3956)

      Emil C. Buruiana, Tinca Buruiana, Georgeta Strat and Mitachi Strat

      Version of Record online: 21 JUL 2005 | DOI: 10.1002/pola.20880

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      A new type of pyrene monomer, 4-chloromethylphenylcarbamoyl-1-oxymethylpyrene, was prepared to be used for the synthesis of photoluminescent polymers. The inferred location of pyrene in three hydrophilic cationic polyurethanes was used to interpret the strong tendency to form excimers of pyrene in solution and in thin films.

    23. Polymerization of 2-hydroxyethyl acrylate in bulk and solution by chemical initiator and by ATRP method (pages 3957–3965)

      Elif Vargün and Ali Usanmaz

      Version of Record online: 21 JUL 2005 | DOI: 10.1002/pola.20867

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      The hydrogel polymers were obtained from 2-hydroxyethyl acrylate (HEA) polymerized in bulk, solution, and atom transfer radical (ATRP) polymerization techniques. The polymers obtained were insoluable in most common solvents. The activation energy for bulk polymerization was 155.8 kJ/mol, which is very high for a free radical polymerization. This is due to the high degree of intermolecular hydrogen bonding, which was also supported by FTIR and TGA analysis. The polymers were characterized by FT-IR, DSC, TGA, and 1H NMR techniques.

    24. Polymerization of n-phenyl maleimide by lanthanide complexes (pages 3966–3972)

      Bei Zhao, Yaorong Wang, Chengrong Lu, Qi Shen and Mingyu Deng

      Version of Record online: 21 JUL 2005 | DOI: 10.1002/pola.20885

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      A series of (Ar′O)2Ln(THF)3 complexes (Ar′O = 2,6-di-tert-butyl phenoxo-; Ln = Sm, Yb, or Eu; THF = tetrahydrofuran) were prepared, and the molecular structure of the Sm complex (2,6-tBu2C6H3O)2Sm(1,2-dimethoxyethane)2 was determined with an X-ray diffractometer. All these divalent lanthanides complexes could alone initiate the polymerization of N-phenyl maleimide. The results showed that the central metals greatly affected the reactivity, and the reactivity order was Sm(II) > Yb(II) > Eu(II). The polymerization yields were higher in THF than in other solvents, and the maximum yields were obtained around 25 °C.

    25. Comparison of the properties of waterborne polyurethane/multiwalled carbon nanotube and acid-treated multiwalled carbon nanotube composites prepared by in situ polymerization (pages 3973–3985)

      Jiyun Kwon and Hando Kim

      Version of Record online: 20 JUL 2005 | DOI: 10.1002/pola.20897

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      Significant information about the molecular motions of waterborne polyurethane (WBPU) chains was obtained by dynamic mechanical thermal analysis. The storage modulus, glass-transition temperatures of the soft and hard segments (Tgs and Tgh, respectively), and ΔTg (TghTgs) of WBPU for WBPU/multiwalled carbon nanotube (CNT) and WBPU/nitric acid treated multiwalled carbon nanotube (A-CNT) composites increased with increasing CNT and A-CNT contents. The peak intensities of the loss modulus and tan δ of both composite systems decreased with increasing CNT and A-CNT contents. The higher reinforcing effect of A-CNT could be attributed to the smaller size and higher polar groups of A-CNT in comparison with CNT.

    26. Electrosyntheses of high-quality poly(5-nitroindole) films in boron trifluoride diethyl etherate containing additional diethyl ether (pages 3986–3997)

      Jingkun Xu, Weiqiang Zhou, Jian Hou, Shouzhi Pu, Liushui Yan and Jingwu Wang

      Version of Record online: 20 JUL 2005 | DOI: 10.1002/pola.20893

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      High-quality poly(5-nitroindole) (PNP) films, with good electrochemical behavior, good thermal stability, good fluorescence properties, and ambient conductivity of 10(−2) S cm−1, were synthesized electrochemically by the direct anodic oxidation of 5-nitroindole in boron trifluoride diethyl etherate containing additional 10% diethyl ether (by volume). To the best of our knowledge, this is the first time that nitro-group-substituted high-quality conducting polymer films have been electrodeposited. As-formed PNP films were thoroughly soluble in the strong polar organic solvent dimethyl sulfoxide and partly soluble in tetrahydrofuran or acetone.

    27. Synthesis, thermal characterization, and tensile properties of alipharomatic polyesters derived from 1,3-propanediol and terephthalic, isophthalic, and 2,6-naphthalenedicarboxylic acid (pages 3998–4011)

      C. P. Roupakias, D. N. Bikiaris and G. P. Karayannidis

      Version of Record online: 20 JUL 2005 | DOI: 10.1002/pola.20886

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      The synthesis, on a laboratory scale, of three alipharomatic polyesters of 1,3-propanediol was realized with the utilization of neat terephthalic or isophthalic acid (new trend) or with the dimethyl ester of 2,6-naphthalenedicarboxylic acid (old technology). A thermal characterization of the three polyesters with various thermoanalytical techniques (thermogravimetry/differential thermal analysis, thermomechanical analysis, and dynamic thermomechanical analysis) was performed, and the work was completed with a short comparative study of the three polyesters with respect to their tensile properties.

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    1. Templateless and surfactantless route to the synthesis of polyaniline nanofibers (pages 4012–4015)

      Guicun Li, Shuping Pang, Hongrui Peng, Zhaobo Wang, Zuolin Cui and Zhikun Zhang

      Version of Record online: 20 JUL 2005 | DOI: 10.1002/pola.20848

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      Polyaniline nanofibers with ramose structues have been synthesized through a templateless and surfactantless method. The diameters of polyanilinie nanofibers decrease with decreasing the concentrations of p-aminobenzenesulfonic acid. These nanofibers can form a porous film associated with the open nanostructures, which may give better peformance in the field of chemical sensors.