Journal of Polymer Science Part A: Polymer Chemistry

Cover image for Vol. 49 Issue 1

1 January 2011

Volume 49, Issue 1

Pages 1–299

  1. Articles

    1. Top of page
    2. Articles
    3. Article
    4. Articles
    1. An efficient avenue to poly(styrene)-block-poly(ε-caprolactone) polymers via switching from RAFT to hydroxyl functionality: Synthesis and characterization (pages 1–10)

      Christina Schmid, Jana Falkenhagen and Christopher Barner-Kowollik

      Article first published online: 13 OCT 2010 | DOI: 10.1002/pola.24299

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      Sulfur-free poly(styrene)-block-poly(ε-caprolactone) polymers with narrow polydispersities were generated by switching thiocarbonyl thio capped (RAFT) polymers into hydroxyl terminated species.

    2. A novel fluorine-containing graft copolymer bearing perfluorocyclobutyl aryl ether-based backbone and poly(methyl methacrylate) side chains (pages 11–22)

      Hao Liu, Yongjun Li, Sen Zhang, Dong Yang, Jianhua Hu and Xiaoyu Huang

      Article first published online: 13 OCT 2010 | DOI: 10.1002/pola.24352

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      A series of novel graft copolymers consisting of perfluorocyclobutyl aryl ether-based backbone and poly(methyl methacrylate) side chains were synthesized by the combination of thermal [2π + 2π] step-growth cycloaddition polymerization of aryl bistrifluorovinyl ether monomer and ATRP of methyl methacrylate.

    3. Synthesis of starlike PtBA-g-PEO amphiphilic graft copolymer via highly efficient Cu-catalyzed SET-NRC reaction at ambient temperature (pages 23–34)

      Yaogong Li, Yaqin Zhang, Sujuan Zhai, Yan Deng, Huiming Xiong, Guolin Lu and Xiaoyu Huang

      Article first published online: 3 NOV 2010 | DOI: 10.1002/pola.24392

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      The first amphiphilic star graft copolymers containing poly(ethylene oxide) side chains were synthesized by the combination of RAFT and highly efficient Cu-catalyzed SET-NRC at ambient temperature.

    4. Protected versus unprotected dextran macroinitiators for ATRP synthesis of Dex-g-PMMA (pages 35–46)

      Ludovic Dupayage, Cécile Nouvel and Jean-Luc Six

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24409

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      Two strategies for the synthesis of amphiphilic dextran-g-poly(methyl methacrylate) glycopolymers (Dex-g-PMMA) have been examined and compared to control the macromolecular parameters of such glycopolymers using ‘grafting from’ concept and Atom Transfer Radical Polymerization. One is involving four steps including a protection/deprotection approach and the second one only two steps. These two types of polysaccharidic macroinitiators differ in term of solubility and of position of the initiators groups on the glucosidic units. Advantages and drawbacks of both types of macroinitiators have finally been discussed.

    5. Nonlinear optical side-chain polymers post-functionalized with high-β chromophores exhibiting large electro-optic property (pages 47–54)

      Xianqing Piao, Xianmin Zhang, Yuichi Mori, Masayuki Koishi, Akinari Nakaya, Shinichiro Inoue, Isao Aoki, Akira Otomo and Shiyoshi Yokoyama

      Article first published online: 11 NOV 2010 | DOI: 10.1002/pola.24410

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      FTC-based nonlinear optical chromophores with large molecular hyperpolarizability have been synthesized and attached to poly[(methyl methacrylate)-co-(2-methacryloyloxyethyl isocyanate)] by post-functionalization reaction. Synthesized side-chain polymers showed excellent solubility in common solvents for prepared high-quality optical films with improved poling efficiency and thermal stability. Electro-optic measurement of the electric-poled films showed electro-optic coefficient of 150 pm/V at the laser wavelength of 1.31 μm. Temporal stability was measured at 85 °C for longer than 500 h.

  2. Article

    1. Top of page
    2. Articles
    3. Article
    4. Articles
    1. High performance semiconducting polymers containing bis(bithiophenyl dithienothiophene)-based repeating groups for organic thin film transistors (pages 55–64)

      Kyung Hwan Kim, Dae Sung Chung, Chan Eon Park and Dong Hoon Choi

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24415

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      New dithienothiophene-containing conjugated polymers, such as poly(2,6-bis(2-thiophenyl-3-dodecylthiophene-2-yl)dithieno[3,2-b;2′,3′-d]thiophene, 4 has been successfully synthesized. Grazing-incidence X-ray diffraction (GI-XRD) gave clear evidence of edge-on orientation of polycrystallites to the substrate. The semiconducting properties of the polymer have been evaluated in organic thin film transistors (OTFTs). The two conjugated polymer 4 exhibits fairly high hole carrier mobilities as high as μave = 0.05 cm2/Vs (ION/OFF = 3.42 × 104) after thermal annealing process. The hole carrier mobilities of the solvent annealed films are comparable to those obtained for a thermally annealed sample, and were one-order higher than those obtained with a pristine sample.

    2. Highly thermostable and low birefringent norbornene-styrene copolymers with advanced optical properties: A potential plastic substrate for flexible displays (pages 65–71)

      Hoang The Ban, Hideaki Hagihara, Yasuo Tsunogae, Zhengguo Cai and Takeshi Shiono

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24416

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      A highly thermostable and low birefringent cyclic olefin copolymer resulting from the vinyl addition copolymerization of norbornene with styrene was successfully synthesized using a substituted fluorenylamidodimethyltitanium catalyst. The prepared copolymer possesses a glass transition temperature as high as polyimide (Tg > 300 °C) and a light transmittance that is almost comparable with that of the conventional optical resins ([T] > 90%). The incorporation of a negative birefringent polystyrene into the positive birefringent polynorbornene effectively reduced the birefringent magnitude of the norbornene-styrene copolymer due to the mutual compensation between these opposite-sign birefringences. With these advanced thermal and optical properties, the vinyl-added norbornene-styrene copolymer satisfies all the rigorous requirements for a polymer to be applied as a flexible substrate for the flexible displays.

  3. Articles

    1. Top of page
    2. Articles
    3. Article
    4. Articles
    1. One-step synthesis of ladder-type fused poly(benzopentalene) derivatives with tunable energy levels by variable substituents (pages 72–81)

      Dong Wang and Tsuyoshi Michinobu

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24419

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      Novel ladder-type conjugated polymers, fused poly(benzopentalene) derivatives, were successfully synthesized from the readily accessible 1,4-dibromo-2,5-diethynylbenzene derivatives by the Pd catalyzed self-polycondensation in one-step with high yields. The variable polymer energy levels and high solubility were achieved by the introduction of suitable substituents, and when the dialkylanilino (DAA) groups were used, the almost defect-free structure of the ladder-type polymers was confirmed by the quantitative tetracyanoethylene (TCNE) addition to the DAA-activated alkynes.

    2. Synthesis and characterization of functional fluorinated telomers (pages 82–92)

      Nelly Durand, Bruno Ameduri and Bernard Boutevin

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24420

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      The synthesis of functional fluorinated telomers by iodine transfer polymerization (ITP) of vinylidene fluoride (VDF) with chain transfer agents (CTAs, C4F9I or C6F13I) initiated by bis(4-tert-butylcyclohexyl) peroxydicarbonate (BBCHPDC) and their spectroscopies, crystallographic, and thermal characterizations are reported.

    3. Highly phosphonated poly(N-phenylacrylamide) for proton exchange membranes (pages 93–100)

      Namiko Fukuzaki, Kazuhiro Nakabayashi, Satoshi Nakazawa, Shigeaki Murata, Tomoya Higashihara and Mitsuru Ueda

      Article first published online: 11 NOV 2010 | DOI: 10.1002/pola.24422

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      The synthesis of phosphonated poly(N-phenylacrylamide) with an ion-exchange capacity (IEC) of 6.72 mequiv/g and its properties such as proton conductivity, water uptake, and oxidative stability have been investigated.

    4. Conjugated polymer covalently modified multiwalled carbon nanotubes for optical limiting (pages 101–109)

      Lijuan Niu, Peipei Li, Yu Chen, Jun Wang, Jinjuan Zhang, Bin Zhang and Werner J. Blau

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24423

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      A new soluble multiwalled carbon nanotubes covalently functionalized with conjugated polymer PCBF is synthesized. This material exhibits prominent broadband optical limiting response at both 532 and 1064 nm.

    5. Modification of polysulfones by click chemistry: Amphiphilic graft copolymers and their protein adsorption and cell adhesion properties (pages 110–117)

      Gorkem Yilmaz, Hojjat Toiserkani, Dilek Odaci Demirkol, Serhan Sakarya, Suna Timur, Yusuf Yagci and Lokman Torun

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24424

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      Well-defined amphiphilic graft copolymer with hydrophobic polysulfone (PSU) backbone and hydrophilic poly(acrylic acid) (PAA) side chains were synthesized by click chemistry and characterized. Protein adsorption characteristics of PSU-g-PAA were studied and found to be reduced when compared to the precursor PSU. This can be attributed to the pendant carboxylic acid functionalities, which readily ionized in neutral and basic media to produce negatively charged carboxylate ions. PSU-g-PAA membrane act as an electrostatic repulsion barrier against the negatively charged BSA, which (like other proteins in blood) carries negative charge in normal blood circumstances. Thus, adsorbed protein amount is found to be low at tested conditions similar with the physiological pH.

    6. Tuning the size of supramolecular single-chain polymer nanoparticles (pages 118–126)

      E. Johan Foster, Erik B. Berda and E. W. Meijer

      Article first published online: 11 NOV 2010 | DOI: 10.1002/pola.24426

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      Both analytical seperation via GPC and careful molecule weight control during synthesis show that it is entirely possible to tune the size of a supramolecular single-chain nanoparticle by tuning the molecular weight of the parent chain. In addition, this report outlines the structural requirements of the pendant supramolecular functional group needed to facilitate the intramolecular folding of a single chain. The difference between individual unimolecular objects and aggregates of single-chain particles as viewed by AFM is also discussed.

    7. One-pot preparation of aromatic poly(azomethine ester) fibrillar crystals using reaction-Induced crystallization (pages 127–137)

      Jin Gong, Yasuhide Yakushi, Tetsuya Uchida, Shinichi Yamazaki and Kunio Kimura

      Article first published online: 11 NOV 2010 | DOI: 10.1002/pola.24427

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      Fibrillar crystals of poly[4-(4-oxybenzylideneamino)benzoyl] were obtained by one-pot polymerization by the crystallization during the polymerization. They were 50–450 nm in width and over 15 μm in length. Molecular chains aligned perpendicular to the long axis of the fibrillar crystals. The fibrillar crystals possessed high crystallinity and exhibited good thermal stability.

    8. Protein–induced aggregation of fluorescent conjugated polyelectrolytes with sulfonate groups: Synthesis and its sensing application (pages 138–146)

      Jung Hyo Lee, Dai Geun Kim, Na Young Kwon, Geun Seok Jang, Ji Hye Son, Minjung Lee, Hye-Jin Cho, Hee-Seok Kweon and Taek Seung Lee

      Article first published online: 11 NOV 2010 | DOI: 10.1002/pola.24428

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      Anionically charged fluorescent conjugated polyelectrolytes are prepared and exhibit blue emission in aqueous solutions but green or red emission in solid form depending on the conjugation length due to intermolecular exciton migration. They show interesting spectroscopic results such as blue-to-green or blue-to-red changes in fluorescence upon exposure to charged proteins, indicating that the polymers have potential applications in fluorescent array systems for detecting proteins.

    9. Synthesis, micellar structures, and multifunctional sensory properties of poly(3-hexylthiophene)-block-poly(2-(dimethylamino)ethyl methacrylate) rod-coil diblock copolymers (pages 147–155)

      Kuan-Kai Huang, Yi-Kai Fang, Jung-Ching Hsu, Chi-Ching Kuo, Wei-Hsuan Chang and Wen-Chang Chen

      Article first published online: 11 NOV 2010 | DOI: 10.1002/pola.24429

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      New conjugated rod-coil block copolymers P3HT-b-PDMAEMA with three different coil lengths were synthesized by the ATRP method. The micelles of P3HT20-b-PDMAEMA43 in water had a reversible size change on heating/cooling cycle or varying the pH values. The micellar structure of three P3HT-b-PDMAEMA copolymers changed from spheres, to vesicles, and finally to larger sphere micelles as the solvent composition varied from 0 to 100 wt % water in the mixed solvent. The different micellar structures of P3HT20-b-PDMAEMA43 solution led to a red-shift on the absorption or photoluminescence spectra and exhibited the emission colors of yellow, orange, red, and dark red with increasing the water content.

    10. Pursuit of reinitiation efficiency of resonance-stabilized monomeric allyl radical generated via “degradative monomer chain transfer” in allyl polymerization (pages 156–163)

      Satoshi Inoue, Takeo Kumagai, Hajime Tamezawa, Hiroyuki Aota, Akira Matsumoto, Katsutoshi Yokoyama, Yasuo Matoba and Michirou Shibano

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24430

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      To understand deeply the allyl polymerization mechanism, the reinitiation efficiency of resonance-stabilized monomeric allyl radical generated via “degradative monomer chain transfer” was pursued, because in allyl polymerization, it is commonly conceived that the monomer chain transfer is essentially a termination reaction. The reinitiation efficiencies of monomeric allyl radical in the temperature range of 80–130 °C were estimated by the dead-end polymerizations of allyl benzoate using a small amount of initiators. Thus, the enhanced reinitiation at a higher temperature could bias the well-known degradative monomer chain transfer characteristic of allyl polymerization toward the chain transfer in common vinyl polymerization.

    11. Controlled grafting of cellulose esters using SET-LRP process (pages 164–173)

      Petr Vlček, Vladimír Raus, Miroslav Janata, Jaroslav Kříž and Antonín Sikora

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24431

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      Cellulose diacetate and acetate butyrate were acylated with 2-bromoisobutyryl bromide or dichloroacetyl chloride to a various degree, giving monofunctional and bifunctional ATRP initiation sites. These were, however, combined with Cu(0) and appropriate ligands and for the first time used for grafting of (meth)acrylate monomers by SET-LRP method in DMSO. Grafting proceeded with acceptable rate at elevated temperature, nevertheless, the reaction conditions had to be optimized with respect to the monomer used. The grafts can be prolonged with other monomer to give block-copolymer-type grafts, e.g., p(HEMA-b-MMA-b-HEMA) amphiphilic triblocks. The products contained almost no catalytic residua and, therefore, did not require additional purification.

    12. Novel superhydrophobic silica/poly(siloxane-fluoroacrylate) hybrid nanoparticles prepared via surface-initiated ATRP and their surface properties: The effects of polymerization conditions (pages 174–183)

      Hai-Jiang Yu and Zheng-Hong Luo

      Article first published online: 11 NOV 2010 | DOI: 10.1002/pola.24434

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      Superhydrophobic silica/poly(siloxane-fluoroacrylate) hybrid nanoparticles were prepared by two-step surface-initiated ATRP. The superhydrophobic property was found to depend on the SI-ATRP of 2,2,3,3,4,4,4-heptafluorobutyl methacrylate (HFBMA). The effects of polymerization conditions, such as the initiator concentration, the molar ratio of monomer and initiator and the polymerization temperature on the SI-ATRP kinetics, and the interrelation between the kinetics and the surface properties of the nanoparticles were investigated. The results showed that the SI-ATRP of HFBMA was well -controlled.

    13. Highly efficient and stable blue-light-emitting copolyfluorene consisting of carbazole, oxadiazole, and charge-trapping anthracene groups (pages 184–191)

      Ruei-Tang Chen, Wen-Fen Su and Yun Chen

      Article first published online: 3 NOV 2010 | DOI: 10.1002/pola.24439

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      A highly efficient and stable blue-light-emitting copolyfluorene (P1) consisting of carbazole, oxadiazole, and charges trapping anthracene groups is synthesized. Polymer light-emitting diodes using P1 as the emitting layer (ITO/PEDOT:PSS/P1/Ca/Al) exhibits excellent current efficiency (5.1 cd/A) with the CIE coordinates of (0.16, 0.11). Doping the copolyfluorene with carbazole, oxadiazole, and anthracene groups significantly improves its electroluminescent performance.

    14. High Tg microspheres by dispersion copolymerization of N-phenylmaleimide with styrenic or alkyl vinyl ether monomers (pages 192–202)

      Swapna Krishnamoorthy, Mehul Haria, Blythe E. Fortier-mcgill, M. A. Jafar Mazumder, Erica I. Robinson, Yan Xia, Nicholas A. D. Burke and Harald D. H. Stöver

      Article first published online: 3 NOV 2010 | DOI: 10.1002/pola.24440

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      Polymer microspheres with high Tg values (165–225 °C) were prepared by dispersion copolymerization of N-phenylmaleimide with styrenic or alkyl vinyl ether comonomers, where the Tg value of the particles could be adjusted through the selection of the appropriate comonomer(s). The image shows the effect of polymerization solvent (ethanol with varying amounts of methyl ethyl ketone) on the size and morphology of styrene-phenylmaleimide particles made by dispersion polymerization.

    15. Size and morphology controllable core cross-linked self-aggregates from poly(ethylene glycol-b-succinimide) copolymers (pages 203–210)

      Chan Woo Park, Hyun Jin Lee, Hee-man Yang, Min-ah Woo, Hyun gyu Park and Jong-Duk Kim

      Article first published online: 3 NOV 2010 | DOI: 10.1002/pola.24441

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      Diverse morphologies of nanostructures with a biocompatible cross-linked core were fabricated from a new type of cross-linkable amphiphilic block copolymers, poly(ethylene glycol)-block-poly(succinimide).

    16. Synthesis and characterization of poly(phenylacetylenes) featuring activated ester side groups (pages 211–224)

      Anja C. Pauly and Patrick Theato

      Article first published online: 8 NOV 2010 | DOI: 10.1002/pola.24442

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      Pentafluorophenyl 4-ethynylbenzoate as an activated ester monomer was (co)polymerized yielding a reactive polyacetylenes. Postpolymerization functionalization with amines was investigated and it was found that poly(pentafluorophenyl 4-ethynylbenzoate) reacted quantitatively even with aromatic amines. The resulting functionalized polymers were characterized by UV-vis spectroscopy.

    17. Energy level tuning of polythiophene derivative by click chemistry-type postfunctionalization of side-chain alkynes (pages 225–233)

      Yuping Yuan and Tsuyoshi Michinobu

      Article first published online: 11 NOV 2010 | DOI: 10.1002/pola.24443

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      A polythiophene derivative substituted with the electron-rich alkynes was subjected to the “click chemistry”-type postfunctionalization by high-yielding TCNE/TCNQ additions. UV–vis–NIR spectra and electrochemical measurements suggested the formation of donor–acceptor chromophores in quantitative yields. As more acceptor molecules were added, both HOMO and LUMO levels of the polymers were more significantly lowered.

    18. Polythiophenes bearing electron-withdrawing groups in the side chain and their application to bulk heterojunction solar cells (pages 234–241)

      Kwang-Hoi Lee, Ho-Jin Lee, Kouji Kuramoto, Yohei Tanaka, Kazuhide Morino, Atsushi Sudo, Tatsuo Okauchi, Akihito Tsuge and Takeshi Endo

      Article first published online: 11 NOV 2010 | DOI: 10.1002/pola.24444

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      Novel polythiophenes PTDCN and PTCNME exhibited very low-lying HOMO energy levels of −5.53 eV and −5.29 eV, respectively, because of the introduction of strong electron-withdrawing groups in the side chains. The photovoltaic properties of the solar cells based on the polymers were investigated. The bulk heterojunction polymer solar cells fabricated by using blend films of polymers as electron donors and PC61BH as electron acceptor exhibited power conversion efficiencies (PCEs) of 0.56% and 0.72% for PTDCN and PTCNME, respectively.

    19. Cobalt-mediated radical polymerization routes to poly(vinyl ester) block copolymers (pages 242–249)

      David N. Bunck, Gregory P. Sorenson and Mahesh K. Mahanthappa

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24445

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      Sequential cobalt-mediated radical polymerizations (CMRP) of vinyl esters such as vinyl acetate, vinyl pivalate, and vinyl benzoate yield well-defined, unimodal poly(vinyl ester) block copolymers with variable molecular weight and narrow polydispersities (Mw/Mn ≤ 1.4) that are shown to microphase separate.

    20. Efficient accelerating effect of carbonyldiimidazole on epoxy-dicyandiamide curing system (pages 250–256)

      Xiang Dong Liu, Atsushi Sudo and Takeshi Endo

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24448

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      CDI was inventively used to accelerate cure of epoxy-DICY system and significant effect was observed. The accelerating mechanism of CDI involves (1) acylation of DICY, (2) release of imidazole, and (3) giving imidazole anion by attack of the alkoxide.

    21. Synthesis and characterization of four alkyl 2-cyanoacrylate monomers and their precursors for use in latent fingerprint detection (pages 257–277)

      Mark Tahtouh, John R. Kalman and Brian J. Reedy

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24449

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      Four novel alkyl 2-cyanoacrylates have been synthesized with functional groups designed to give them isolated absorption bands in relatively vacant regions of the mid-infrared spectrum. These spectroscopic properties allow them to be used for the development and subsequent mid-infrared spectral imaging of fingerprints on difficult backgrounds in forensic science applications. The fingerprint seen here was developed with 2-cyanoethyl 2-cyanoacrylate, whose absorption spectrum is used to form the image.

    22. Influence of the poly(propylene imine) generation in the LC properties of ionic codendrimers bearing fluorinated and perhydrogenated chains (pages 278–285)

      Silvia Hernández-Ainsa, Joaquín Barberá, Mercedes Marcos and José Luis Serrano

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24450

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      The generation of poly(propylenemine) codendrimer ionically substituted with perhydrogenated and fluorinated acids produces a remarkable effect in the supramolecular organization in the liquid crystal state. By contrast, no difference in the surface arrangement is observed by atomic force microscopy, thus the compounds self-assemble in homogeneous monolayers.

    23. Porphyrin-functionalized amphiphilic diblock copolypeptides for photodynamic therapy (pages 286–292)

      Ze-Yong Li, Hui-Yuan Wang, Cao Li, Xiao-Lu Zhang, Xiao-Jun Wu, Si-Yong Qin, Xian-Zheng Zhang and Ren-Xi Zhuo

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24451

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      A series of amphiphilic diblock copolypeptides (ADCs), 5-(4-aminophenyl)-10,15,20-triphenyl-porphyrin (APP) conjugated poly(l-leucine)-block-polylysine (APP-LnKm) with different molar ratios of L-leucine unit and lysine unit were designed and synthesized. It was found that the micellar structure was formed by the self-assembly of the ADCs. APP-L109K186 micelles exhibited no significant dark cytotoxicity and high photodynamic therapy efficacy against HepG2 and HeLa cells, which indicated APP-L109K186 micelles could be a novel carrier for cancer therapy.

    24. Optically active helical polymer from radical polymerization of menthyl vinyl ketone (pages 293–299)

      Shi Wu, Nianfa Yang, Yanling Liu, Jing Cao, Hai Hu, Yunkai Sun and Ji Liu

      Article first published online: 18 NOV 2010 | DOI: 10.1002/pola.24452

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      Menthyl vinyl ketone (MVK) was radically polymerized to obtain poly-MVK with excess of one-handed helical sense. The radically polymerized poly-MVK kept stable one-handed helical conformation in solution. The optical rotation and the CD intensity of the radically polymerized poly-MVK were larger than that of the anionically polymerized poly-MVK. The molecular weight of the radically polymerized poly-MVK was much larger than that of the THF-soluble part of the anionically polymerized poly-MVK.

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