Journal of Polymer Science Part A: Polymer Chemistry

Cover image for Vol. 45 Issue 14

15 July 2007

Volume 45, Issue 14

Pages 2835–3133

  1. Articles

    1. Top of page
    2. Articles
    3. Rapid Communications
    4. Notes
    1. Role of architecture and molecular weight in the formation of tailor-made ultrathin multilayers using dendritic macromolecules and click chemistry (pages 2835–2846)

      Robert Vestberg, Michael Malkoch, Matthew Kade, Peng Wu, Valery V. Fokin, K. Barry Sharpless, Eric Drockenmuller and Craig J. Hawker

      Version of Record online: 1 JUN 2007 | DOI: 10.1002/pola.22178

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      The high efficiency and mild reaction conditions associated with the Cu(I) catalyzed cycloaddition of azides and alkynes were exploited for the covalent layer-by-layer synthesis of dendritic thin films on silicon wafers. The layer-by-layer self assembly process proceeds under ambient conditions and was monitored by ellipsometry, XPS and ATR-IR which showed extremely regular growth of the dendritic thin films. Film thickness could be accurately controlled by both the size/generation number of the dendrimers as well as the number of layers. In comparison with linear analogues, the growth of the dendritic films was significantly more controlled and defect-free with each layer being thinner than the corresponding films prepared from the isomeric linear polymers, demonstrating the well-defined, 3-dimensional nature of the dendritic architecture.

    2. Low-temperature controlled free-radical polymerization of vinyl monomers in the presence of a novel cyclic dixanthate under γ-ray irradiation (pages 2847–2854)

      Daoben Hua, Xueping Ge, Jing Tang, Xiulin Zhu, Ruke Bai and Caiyuan Pan

      Version of Record online: 31 MAY 2007 | DOI: 10.1002/pola.22040

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      The influence of a low temperature on the controlled free-radical polymerization of methyl acrylate has been reported for the first time in the presence of a novel cyclic dixanthate under γ-ray irradiation (80 Gy min−1). The lower the temperature is, the more polymerization control there is, and the more cyclic the polymers are, and this may be related to the reduced diffusion rate and the suppressed chain-transfer reaction at the low temperature, unlike conventional reversible addition–fragmentation chain transfer processes.

    3. Synthesis and properties of fluorine-containing poly(aryl ether oxadiazole)s (pages 2855–2866)

      Natsuko Sato, Ken Tanaka, Shunsuke Masaki, Shinichi Yamazaki, Kunio Kimura and Ai Nishichi

      Version of Record online: 31 MAY 2007 | DOI: 10.1002/pola.22041

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      Fluorine-containing poly(aryl ether 1,3,4-ozadiazole)s were synthesized by the nucleophilic aromatic substitution reaction of 2,5-bis(2,3,4,5,6-pentafluorophenyl)-1,3,4-oxadiazole and various bisphenols in the presence of potassium carbonate. The polymerizations were carried out at 30 °C in 1-methyl-2-pyrrolidinone to avoid the crosslinking reaction. The obtained polymers connected at para carbons to the 1,3,4-oxidiazole ring of 2,5-bis(2,3,4,5,6-pentafluorophenyl)-1,3,4-oxadiazole. They showed excellent solubility, high transparency, high glass transition temperatures from 157 to 257 °C, and good thermal stability. They also exhibited excellent hydrophobicity due to the incorporation of the 2,3,5,6-tetrafluoro-1,4-phenylene moiety.

    4. Synthesis and characterization of novel π-conjugated polymers with phosphole ring derivatives (pages 2867–2875)

      Hai-Sub Na, Yasuhiro Morisaki, Yasuhiro Aiki and Yoshiki Chujo

      Version of Record online: 1 JUN 2007 | DOI: 10.1002/pola.22043

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      Three kinds of novel π-conjugated polymers having a phosphole ring with a five-member fused carbocycle or modified phosphole units in the polymer main chain were synthesized by the Sonogashira coupling reaction. The structure and optical properties of the new monomers and their polymers were examined in detail. The obtained polymers exhibited moderate bluish-green or green photoluminescence in solution.

    5. Synthesis and photophysical properties of Rhodamine B dye-bearing poly(isobutyl methacrylate-co-2,2,2-trifluoroethyl methacrylate) as a temperature-sensing polymer film (pages 2876–2885)

      Makoto Obata, Mako Morita, Kayoko Nakase, Kazunori Mitsuo, Keisuke Asai, Shiho Hirohara and Shigenobu Yano

      Version of Record online: 1 JUN 2007 | DOI: 10.1002/pola.22044

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      To develop a novel temperature-sensitive paint, methacrylamide monomers bearing Rhodamine B dye were synthesized and polymerized with isobutyl methacrylate and 2,2,2-trifluoroethyl methacrylate to afford Rhodamine B-pendant oxygen-permeable polymers. The film of the Rhodamine B-pendant polymer emits temperature-dependent fluorescence, which is suitable for temperature correction in pressure-sensitive paint application.

    6. Synthesis of dithiocarbamate bearing azobenzene group and use for RAFT polymerization of vinyl monomers (pages 2886–2896)

      Xiaoming Wan, Xiulin Zhu, Jian Zhu, Zhengbiao Zhang and Zhenping Cheng

      Version of Record online: 4 JUN 2007 | DOI: 10.1002/pola.22045

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      A novel dithiocarbamate bearing azobenzene group, 2-(phenylazo-phenoxy-carbonyl) prop-2-yl 9H-carbazole-9-carbodithioate (APCDT), was synthesized and used as a RAFT agent in the polymerization of methyl methacrylate (MMA). The results showed that the controllability to the polymerization of MMA was promoted with APCDT as RAFT agent compared to 2-(ethoxycarbonyl) prop-2-yl 9H-carbazole-9-carbodithioate (EPCDT), which was attributed to the higher chain transfer constant of APCDT than that of EPCDT. APCDT was also an effective RAFT agent for the polymerization of St and MA. Well-defined carbazole and azobenzene group labeled polymer was successfully prepared via RAFT polymerization.

    7. Synthesis and properties of polyimides derived from 1,4-bis(4-aminophenoxy)-2-(6-oxido-6H-dibenz[c,e] [1,2]oxaphosphorin-6-yl) phenylene (pages 2897–2912)

      Ching Hsuan Lin and Chun Hung Lin

      Version of Record online: 1 JUN 2007 | DOI: 10.1002/pola.22046

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      A new phosphorus-containing aromatic diamine (3) was synthesized by nucleophilic aromatic substitution and catalytic hydrogenation. And, a series of light color, flexible and creasable polyimides with high molecular weight, high glass transition, high thermal stability, improved organo-solubility, and good oxygen plasma resistance were synthesized from the condensation of (3) with various aromatic dianhydrides in DMAc, followed by thermal imidization.

    8. Modular synthesis of ABC type block copolymers by “click” chemistry (pages 2913–2924)

      Joost A. Opsteen and Jan C. M. van Hest

      Version of Record online: 1 JUN 2007 | DOI: 10.1002/pola.22047

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      A poly(methyl acrylate)-block-polystyrene-block-poly(tert-butyl acrylate) ABC type triblock copolymer was successfully synthesized in a modular fashion by performing two successive “click” coupling reactions of polymeric precursors onto a heterotelechelic polystyrene central block. This methodology required full protection of the acetylene end group of polystyrene to prevent it from involving in the first “click” reaction, which could lead to linear chain extension or the formation of cyclic products.

    9. Synthesis and characterization of a polyfluorene containing carbazole and oxadiazole dipolar pendent groups and its application to electroluminescent devices (pages 2925–2937)

      Mao-Chuan Yuan, Ping-I Shih, Chen-Han Chien and Ching-Fong Shu

      Version of Record online: 1 JUN 2007 | DOI: 10.1002/pola.22048

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      Both spectral overlap and individual energy level matching between the host and guest are crucial features affecting the performance of the electrophosphorescence devices. As a result, the maximum external quantum efficiency of the PF-CBZ-OXD blend reached as high as 8.6% (8.8 cd/A) at 23.0 mA/cm2; on the other hand, the PF-TPA-OXD blend, which did not feature an efficient charge trapping mechanism in its EL process, exhibited relatively poor performance.

    10. White electroluminescence from a single polymer: A blue-emitting polyfluorene incorporating orange-emitting benzoselenadiazole segments on its main chain (pages 2938–2946)

      Chen-Han Chien, Ping-I Shih and Ching-Fong Shu

      Version of Record online: 1 JUN 2007 | DOI: 10.1002/pola.22049

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      By carefully controlling the concentrations of low-energy-emitting species, partial energy transfer from a blue-fluorescent polyfluorene backbone to orange-fluorescent segments led to a single copolymer exhibiting two balanced blue and orange emissions simultaneously and emitting white light.

    11. Synthesis of well-defined glycidyl methacrylate based block copolymers with self-activation and self-initiation behaviors via ambient temperature atom transfer radical polymerization (pages 2947–2958)

      Ping Jiang, Yi Shi, Pengsheng Liu and Yuanli Cai

      Version of Record online: 4 JUN 2007 | DOI: 10.1002/pola.22050

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      Well-defined glycidyl methacrylate (GMA) based di- and triblock copolymers, with self-activation and self-initiation behaviors by incorporation of 2-(diethylamino) ethyl methacrylate (DEA) blocks were synthesized via ambient temperature atom transfer radical polymerization. The stability of GMA pendant oxirane rings in tertiary amine environments at ambient temperature was investigated. More importantly both self-activation behavior in the oxirane ring opening addition reaction and self-initiation behavior in post-cure oxirane ring opening cross-linking of these block copolymers were evidenced by 1H NMR studies.

    12. Hyperbranched poly(ether–urea)s using AB2-type blocked isocyanate monomer and azide monomer: Synthesis, characterization, reactive end functionalization, and copolymerization with AB monomer (pages 2959–2977)

      Mahalingam Vanjinathan, A. Raghavan and A. Sultan Nasar

      Version of Record online: 4 JUN 2007 | DOI: 10.1002/pola.22051

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      The first example of hyperbranched poly(aryl-ether-urea)s and poly(aryl-alkyl-ether-urea)s were synthesized using AB2-type blocked isocyanate and azide monomers respectively. Hyperbranched poly(aryl-ether-urea) copolymers were also synthesized using functionally similar AB2- and AB-type blocked isocyanate monomers. Molecular weights (Mw) of the polymer were found vary from 1.8 × 103 to 6.5 × 105. The values of degree of branching (DB) of hyperbranched poly(aryl-ether-urea) and its copolymers ranged from 87 to 54%. All the polymers were found thermally stable up to 300 °C. It was found that Tg's of poly(aryl-alkyl-ether-urea)s were significantly less compared to poly(aryl-ether-urea)s. Functionalized end-capping of poly(aryl-ether-urea) were carried out using phenylchloroformate and di-t-butyl dicarbonate (Boc)2O.

    13. Synthesis of self-photosensitizing polyesters containing donor–acceptor norbornadiene moieties and benzophenone groups and their photochemical reactions (pages 2978–2988)

      Yoshitomo Ono, Naoyuki Kawashima, Hiroto Kudo, Tadatomi Nishikubo and Takabumi Nagai

      Version of Record online: 4 JUN 2007 | DOI: 10.1002/pola.22052

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      Novel self-photosensitizing NBD polymers were synthesized in good yields by the ring-opening copolymerization of a glycidyl ester carrying a benzophenone derivative as a photosensitizing group and D-A NDC monoglycidyl ester derivatives with D-A NDCAn using TPPB as a catalyst. The molecular weight of these polyesters was about 4,000. All the synthesized NBD polymers isomerized smoothly to the corresponding QC polymers upon UV irradiation in the THF solution and in the film state. The rate of photoisomerization of the D-A NBD moieties in these polymers was higher than that of the D-A NBD moieties in the polymer having no photosensitizing group in the film state and in dilute solution. The photo-irradiated polymers having QC moieties released thermal energies of 146–180 J/g. The D-A NBD moieties contained in these NBD polymers possessed fair to good fatigue resistance.

    14. Doping phosphoric acid in polybenzimidazole membranes for high temperature proton exchange membrane fuel cells (pages 2989–2997)

      Ronghuan He, Qingfeng Li, Jens Oluf Jensen and Niels J. Bjerrum

      Version of Record online: 4 JUN 2007 | DOI: 10.1002/pola.22053

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      The doping chemistry of polybenzimidazole (PBI) with phosphoric acid was studied using the Scatchard method. The energy distribution of the acid complexation in the polymer membranes is heterogeneous, that is, there are two types of polymer sites with different affinities to the acid. The dissociation constants for the doping acid on these two types of polymer sites are estimated.

    15. Preparation and properties of novel thermotropic liquid crystalline hyperbranched polyesters composed of five-membered heterocyclic mesogen by A2 + B3 approach (pages 2998–3008)

      Moriyuki Sato, Yoichi Matsuoka and Isao Yamaguchi

      Version of Record online: 4 JUN 2007 | DOI: 10.1002/pola.22054

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      New thermotropic liquid crystalline (LC) hyperbranched (HB) polyesters containing 2,5-diphenyl-1,3,4-thiadiazole (DTD) unit as mesogen in the interiors were prepared at various molar ratios (A2/B3) by melt and solution polycondensations via the A2 + B3 approach and their LC and optical properties were investigated. The LC properties of HB polymers depended on the polymerization methods and the feed molar ratios. The polymers prepared using the solution polycondensation formed highly-ordered tilted smectic phases. In all the HB polymers, absorption and photoluminescenct (PL) peak maxima with blue emission on the basis of the DTD unit were observed in solutions and in solid state.

    16. Photopolymerization kinetics of ionic liquid monomers derived from the neutralization reaction between trialkylamines and acid-containing (meth)acrylates (pages 3009–3021)

      Zulma Jiménez, Christopher Bounds, Charles E. Hoyle, Andrew B. Lowe, Hui Zhou and John A. Pojman

      Version of Record online: 4 JUN 2007 | DOI: 10.1002/pola.22055

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      Polymerizable ionic liquids were synthesized from the neutralization reaction between trialkylamines and acid-containing (meth)acrylates in order to study the kinetics of their photopolymerization. The mono(meth)acrylate ionic liquids showed low or moderate increases in rate compared to their monofunctional analogues. The difunctional (meth)acrylate ionic liquids exhibited rates typical of traditional di(meth)acrylates although the (meth)acrylates were not covalently attached to the same molecule.

    17. Ring-opening metathesis polymerization of new norbornene-based monomers containing various chromophores (pages 3022–3031)

      Der-Jang Liaw, Kun-Li Wang, Kueir-Rarn Lee and Juin-Yih Lai

      Version of Record online: 4 JUN 2007 | DOI: 10.1002/pola.22056

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      Novel pure exo-functional norbornene monomers containing various chromophores such as fluorene, pyrene, and carbazole were successfully prepared via the Diels–Alder reaction and condensation reaction. Linear polymers and diblock copolymers of these norbornene derivatives were carried out via ring-opening metathesis polymerization using Grubbs catalyst I. All the chromophore-containing polymers showed excellent solubility in various organic solvents. The glass transition temperatures of polynorbornenes containing various chromophores were determined to be 80–109 °C. The photoluminescence spectra of these polymers containing chromophores were discussed.

    18. Selective polymerization of propylene oxide by a tin phosphate coordination polymer (pages 3032–3041)

      Christine Schütz, Torsten Dwars, Christoph Schnorpfeil, Jörg Radnik, Michael Menzel and Udo Kragl

      Version of Record online: 4 JUN 2007 | DOI: 10.1002/pola.22057

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      Tin phosphate coordination polymers show high activity in the selective polymerization of epoxides. Investigations of organotin phosphate condensates in the stereoregular polymerization of propylene oxide, including the properties controlling the molecular weight of the resulting poly(propylene oxide)and structural and mechanistic studies, are presented. Moreover, very good isotacticities over 80% and good activities have been observed.

    19. Polymerization of carboxylic ester functionalized norbornenes catalyzed by (η3-allyl)palladium complexes bearing N-heterocyclic carbene ligands (pages 3042–3052)

      Il Gu Jung, Junhyeok Seo, Young Keun Chung, Dong Mok Shin, Sung-Ho Chun and Seung Uk Son

      Version of Record online: 5 JUN 2007 | DOI: 10.1002/pola.22060

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      In situ generated cationic allylpalladium complexes bearing N-heterocyclic carbene ligands are active catalysts for the addition polymerization of norbornene derivatives with an ester group containing a large portion of endo-isomers.

    20. Electron-pair-donor reaction order in the cationic polymerization of isobutylene coinitiated by AlCl3 (pages 3053–3061)

      Yan Li, Yixian Wu, Xu Xu, Lihu Liang and Guanying Wu

      Version of Record online: 5 JUN 2007 | DOI: 10.1002/pola.22061

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      The cationic polymerizations of isobutylene (IB) initiated by an H2O/AlCl3 system were carried out in a mixture of n-hexane and methylene dichloride (n-hexane/CH2Cl2 = 60/40 v/v) at −50 °C in the presence of various external electron pair donors (EDs) such as methyl benzoate. The external EDs with weak donicity remarkably influenced the cationic polymerization of IB. It was found that polymers with high molecular weights and relatively narrow molecular weight distributions were obtained in the presence of the EDs. The kinetic orders of the EDs were remarkably dependent on their chemical structure, steric hindrance from moieties, and concentration in the polymerization system, and there existed an inflection point for reaction order changes.

    21. Synthesis and morphology of an iron oxide/polystyrene/poly(isopropylacrylamide-co-methacrylic acid) thermosensitive magnetic composite latex with potassium persulfate as the initiator (pages 3062–3072)

      Chia-Fen Lee, Yu-Hui Chou and Wen-Yen Chiu

      Version of Record online: 5 JUN 2007 | DOI: 10.1002/pola.22062

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      In this work, an iron oxide/polystyrene/poly(N-isopropylacryl amide-co-methacrylic acid) thermosensitive magnetic composite latex was synthesized by the method of two-stage emulsion polymerization. The iron oxide particles were prepared by a traditional coprecipitation method and then surface-treated with either a PAA oligomer or lauric acid to form a stable ferrofluid. The effects of the ferrofluids on the reaction kinetics, morphology, and particle size of the latex were discussed. A reaction mechanism was proposed in accordance with the morphology observation of the latex particles. The thermosensitive property of the thermosensitive magnetic composite latex was also studied.

    22. Synthesis of fluorene-based high performance polymers. I. Poly(arylene thioether)s with excellent solubility and high refractive index (pages 3073–3082)

      Surasak Seesukphronrarak, Shinichi Kawasaki, Kana Kobori and Toshikazu Takata

      Version of Record online: 6 JUN 2007 | DOI: 10.1002/pola.22063

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      Several poly(arylene thioether)s (PTEs) containing a fluorene moiety were synthesized by the polycondensation of masked dithiols such as 9,9-bis(4-(N,N-dimethyl-S-carbamoyl)phenyl)fluorene and various difluoroarenes. Most PTEs exhibited remarkably high refractive index values in a range of 1.66–1.72 at 589 nm, and had very low degrees of birefringence properties.

    23. Preparation of polymers having hole and electron transport units by Friedel–Crafts reaction (pages 3083–3089)

      Takashi Washizu, Yuanfu Pei, Jaekook Ha, Martin Vacha, Kuniko Tani, Kenji Ogino and Hisaya Sato

      Version of Record online: 6 JUN 2007 | DOI: 10.1002/pola.22064

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      Polymers having a tetraphenyldiaminobenzidine unit and ozadiazole (BTPD-BCO) and anthracene (BTPD-BCA) were prepared by condensation polymerization using Friedel–Crafts reaction. Hole and electron drift mobility of the polymers were measured by the time-of-flight (TOF) method. The hole drift mobility of both BTPD-BCO and BTPD-BCA was 7.4 × 10−5 cm2 V−1 s−1. The electron drift mobilities of BTPD-BCO and BTPD-BCA were 6.5 × 10−5 cm2 V−1 s−1 and 5.2 × 10−6 cm2 V−1 s−1, respectively.

    24. Polyester oligodiols by cationic AM copolymerization of L,L-lactide and ε-caprolactone initiated by diols (pages 3090–3097)

      Małgorzata Baśko and Przemyslaw Kubisa

      Version of Record online: 6 JUN 2007 | DOI: 10.1002/pola.22065

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      Cationic copolymerization of L,L-lactide (LA) and ε-caprolactone (CL) initiated by low molecular weight diols in the presence of acid catalyst gives corresponding copolyesters terminated at both ends with hydroxyl groups with practically quantitative yield. The microstructure of copolymers and the nature of the end-groups are governed by transesterification rather then by the kinetics of comonomers incorporation.

    25. Kinetics of methyl methacrylate and n-butyl acrylate copolymerization mediated by 2-cyanoprop-2-yl dithiobenzoate as a RAFT agent (pages 3098–3111)

      Jing Gao, Yingwu Luo, Rui Wang, Bogeng Li and Shiping Zhu

      Version of Record online: 6 JUN 2007 | DOI: 10.1002/pola.22067

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      In the presence of 2-cyanoprop-2-yl dithiobenzoate (CPDB), the rate of the RAFT copolymerization of methyl methacrylate (MMA) and n-butyl acrylate (BA) showed a peculiar behavior that is in sharp contrast to conventional free radical polymerization. The rate decreased with an increasing BA fraction and reached the lowest point at fBA ∼ 0.8 as shown in the figure. This behavior was attributed to a RAFT retardation effect. A theory was developed to quantitatively describe the RAFT copolymerization kinetics.

  2. Rapid Communications

    1. Top of page
    2. Articles
    3. Rapid Communications
    4. Notes
    1. You have free access to this content
      Molecular weight distributions from size separation data for hyperbranched polymers (pages 3112–3115)

      Dominik Konkolewicz, Angus A. Gray-Weale and Robert G. Gilbert

      Version of Record online: 4 JUN 2007 | DOI: 10.1002/pola.22059

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      Size-separation characterization techniques such as size-exclusion chromatography separate polymers by hydrodynamic volume, not molecular weight; this makes it impossible to directly obtain the true molecular weight distribution, because each elution slice at a given hydrodynamic volume contains a range of molecular weights (“local polydispersity”). Simulations are used to show that, for randomly hyperbranched polymers, this spread of molecular weights is narrow for all except very low molecular weights. To a good approximation, size-exclusion techniques give the actual molecular weight distribution for hyperbranched polymers. This applies to synthetic polymers such as polyglycerol, the natural polymer glycogen, and others.

    2. You have free access to this content
      Liquid crystalline photoactive hyperbranched and linear benzylidene polyester with terminal epoxy and pendant hydroxyl groups (pages 3116–3123)

      M. Murali, V. Srinivasa Rao and A. B. Samui

      Version of Record online: 7 JUN 2007 | DOI: 10.1002/pola.22066

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      Epoxy-terminated novel photoactive hyperbranched polymers were synthesized with a 0.52 degree of branching. The polymers exhibited nematic mesosphase and intermolecular photo cycloaddition. The hyperbranched polymers exhibited faster photoresponsive behavior, compared to that of linear polymers.

  3. Notes

    1. Top of page
    2. Articles
    3. Rapid Communications
    4. Notes
    1. You have free access to this content
      Syntheses and characterization of water-soluble C60–curdlan sulfates for biological applications (pages 3124–3128)

      Cezar Ungurenasu and Mariana Pinteala

      Version of Record online: 6 JUN 2007 | DOI: 10.1002/pola.22010

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      Curdlan was esterified with bromoalkyl acids and then reacted with sodium azide to give 6-azidoalkyl-6-deoxycurdlan esters. The resulting azidocurdlan esters were then reacted with pyridine/SO3 to give the corresponding sulfates. The addition of these curdlan sulfates to C60 at 40 °C afforded triazol-bridged C60-spacer-curdlan sulfates, whereas the addition reaction at 120 °C yielded aza-bridged C60-spacer-curdlan sulfates.

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      Synthesis of controlled rod–coil block copolymers by a macroinitiator method: Chain-growth polycondensation for an aromatic polyamide from a polystyrene macroinitiator (pages 3129–3133)

      Sunwook Kim, Yoichi Kakuda, Akihiro Yokoyama and Tsutomu Yokozawa

      Version of Record online: 6 JUN 2007 | DOI: 10.1002/pola.22042

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      For the synthesis of well-defined block copolymers of polystyrene and N-octyl poly(p-benzamide) as novel rod–coil block copolymers, the chain-growth polycondensation of phenyl 4-(octylamino)benzoate was carried out from polystyrene macroinitiators with the phenoxycarbonyl end group in the presence of a base. The obtained block copolymers self-assembled in 2-propanol, which was a selective solvent for the polyamide unit, to give submicrometer-sized, spherical aggregates.

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