Journal of Polymer Science Part A: Polymer Chemistry

Cover image for Vol. 50 Issue 18

15 September 2012

Volume 50, Issue 18

Pages i–iv, 3691–3922

  1. Cover Image

    1. Top of page
    2. Cover Image
    3. Rapid Communication
    4. Articles
    5. Notes
    6. Erratum
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      Cover Image, Volume 50, Issue 18 (pages i–ii)

      Version of Record online: 7 AUG 2012 | DOI: 10.1002/pola.26297

      Thumbnail image of graphical abstract

      A deprotonation process at the 4-CH group of a-amino acid N-carboxyanhydride (NCA) in the presence of rare earth metallic tris[bis(trimethylsilyl)amide] ((TMSN)3Ln) is presented by J. Ling, H. Peng, and Z. Shen on page 3743. This long-term neglected reaction shows the acidity of the 4-CH group, not only explaining the racemization phenomenon of NCA in a strong base environment but also supporting that the proposed 4-CH-depronated NCA is responsible for N-substitute NCA polymerization. In addition, (TMSN)3Ln is effective for preparing homo-polypeptides and block co-polypeptides with low molecular weight distributions (generally below 1.3).

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      Inside Cover, Volume 50, Issue 18 (pages iii–iv)

      Version of Record online: 7 AUG 2012 | DOI: 10.1002/pola.26298

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      Bis[N-(4-carboxyphenyl)phtalimidyl]dimethylsilane is prepared and used to build novel hydrogen-bonded supramolecular polymers as a result of co-crystallization with pyridine derivatives: 4,40-bipyridyl (SP1), 1,2-bis(4-pyridyl)ethylene (SP2), and 4,40-azopyridine (SP3), as presented on page 3775 by M.-F. Zaltariov, M. Cazacu, S. Shova, A. Vlad, I. Stoica, and E. Hamciuc. The figure shows a fragment of the 3D two-component supramolecular architecture in the crystal structure of SP3 that arises from the extended system of OAH˙˙˙N and CAH˙˙˙O hydrogen bonds. The 3D packing in the SP3 structure essentially results from the parallel packing of the wavy layers in (011) orientation.

  2. Rapid Communication

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    3. Rapid Communication
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      Semi-random P3HT analogs via direct arylation polymerization (pages 3691–3697)

      Andrey E. Rudenko, Calvin A. Wiley, Shiloh M. Stone, John F. Tannaci and Barry C. Thompson

      Version of Record online: 4 JUN 2012 | DOI: 10.1002/pola.26175

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      Semi-random P3HT analogs and P3HT were synthesized by direct arylation polymerization (DARP) and Stille polycondensation. In several cases, both methods provide polymers with similar molecular weights and polydispersities. Although these two synthetic protocols are strategically similar, preliminary evidence suggests that they give different linkage patterns in the polymers. This translates into different polymer properties as studied by UV–vis, GIXRD, 1H NMR, 13C NMR, DSC, and TGA.

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      A remote photochemical reaction for surface modification of polymeric substrate (pages 3698–3702)

      Changwen Zhao, Zhengdong Zhang and Wantai Yang

      Version of Record online: 11 JUN 2012 | DOI: 10.1002/pola.26179

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      A photo-activated gas / liquid reactive fluid technique inspired by natural photosynthesis process was developed. This reactive fluid could interact with the surface of polymeric substrates not exposed to UV ultraviolet irradiation, and resulted in a direct surface modification or surface grafting.

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      Synthesis of graft copolymers based on selective living cationic polymerization using an acetal group with a combination of Lewis acids (pages 3703–3709)

      Hiroaki Shimomoto, Hirotoshi Yoshida, Shokyoku Kanaoka and Sadahito Aoshima

      Version of Record online: 7 JUN 2012 | DOI: 10.1002/pola.26186

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      Graft copolymers with various combinations of backbones and branch chains were synthesized using a new vinyl monomer containing an acetal pendant group in conjunction with a combination of metal halides by selective living cationic polymerization without any functional group transformations.

  3. Articles

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    1. Melt transesterification and characterization of segmented block copolyesters containing 2,2,4,4-tetramethyl-1,3-cyclobutanediol (pages 3710–3718)

      Musan Zhang, Robert B. Moore and Timothy E. Long

      Version of Record online: 4 JUN 2012 | DOI: 10.1002/pola.26176

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      Conventional melt transesterification successfully produced high molecular weight segmented copolyesters. A rigid, high-Tg polyester precursor containing the cycloaliphatic monomers, 2,2,4,4-tetramethyl-1,3-cyclobutanediol and dimethyl-1,4-cyclohexane dicarboxylate, allowed subsequent polymerization with monomers comprising the low-Tg block and yielded polymers that exhibited enhanced mechanical properties compared to non-segmented copolyester controls. Further investigations with atomic force microscopy uncovered unique needle-like, interconnected, microphase separated surface morphologies. Small-angle X-ray scattering confirmed the presence of microphase separation in the segmented copolyesters bulk morphology.

    2. Efficient polymer passivation of ligand-stripped nanocrystal surfaces (pages 3719–3727)

      Jennifer T. Duong, Mark J. Bailey, Teresa E. Pick, Patrick M. McBride, Evelyn L. Rosen, Raffaella Buonsanti, Delia J. Milliron and Brett A. Helms

      Version of Record online: 4 JUN 2012 | DOI: 10.1002/pola.26178

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      Colloidal nanocrystals are transferred into water with functional polymer coatings using a straightforward two-step method. Native hydrophobic ligands are first removed using trialkyloxonium salts to reveal a bare nanocrystal surface. This is followed by repassivation with polyacrylic acid-derived polymers, which can be prepared by controlled radical polymerization techniques (e.g., RAFT) with specific side-chain and end-group functionality. As the approach is general to all classes of nanocrystals, these hybrids can now be more deliberately prepared to task than has been possible previously.

    3. Group 4 complexes bearing alkoxide functionalized N-heterocyclic carbene ligands as catalysts in the polymerization of olefins (pages 3728–3735)

      Chiara Costabile, Carmen Bocchino, Mariagrazia Napoli and Pasquale Longo

      Version of Record online: 4 JUN 2012 | DOI: 10.1002/pola.26183

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      The synthesis, characterization, and catalytic behavior of octahedral zirconium catalysts bearing [NHC-O] ligands presenting ethenyl and cyclohexenyl alkoxide groups as N-substituents have been reported. Both catalysts activated by methylalumoxane were able to promote the polymerization of ethylene and propylene. In particular, in the presence of both catalytic systems, highly isotactic polypropylene together with an atactic fraction was obtained. DFT studies gave indications on the species possibly involved in the polymerizations.

    4. In situ access to white light-emitting fluorescent polymer nanocomposites via plasma-ignited frontal polymerization (pages 3736–3742)

      Jin Zhou, Wen-Qi Tang, Cai-Feng Wang, Li Chen, Qiaoling Chen and Su Chen

      Version of Record online: 8 JUN 2012 | DOI: 10.1002/pola.26187

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      White light-emitting CdS-poly(HEA-co-NVK) nanocomposites were prepared via plasma-ignited frontal polymerization, which can be conveniently applied onto a commercial UV-light-emitting diode (LED) for practical white light applications, exhibiting potential application as QD-polymer nanocomposite down-conversion LEDs.

    5. Deprotonation reaction of α-amino acid N-carboxyanhydride at 4-CH position by yttrium tris[bis(trimethylsilyl)amide] (pages 3743–3749)

      Jun Ling, Hui Peng and Zhiquan Shen

      Version of Record online: 25 MAY 2012 | DOI: 10.1002/pola.26156

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      Rare earth tris[bis(trimethylsilyl)amide] (TMSN)3Ln (Ln = Sc, Y, La, Dy, and Lu) compounds are effective catalysts which can be used to prepare homopolypeptides and block copolypeptides with narrow molecular weight distributions (MWDs ≤ 1.3). In the initiation step, when (TMSN)3Y reacts with equivalent L-alanine N-carboxyanhydride (ALA NCA), the 4-CH of NCA is found to be deprotonated in addition to the 3-NH position. This result proves the acidity of 4-CH in NCA which is a direct evidence for racemization phenomenon of NCA and strong base-catalyzed N-substituted NCA polymerization.

    6. Improving the control of styrene polymerization at 60 °C using a dialkylated α-hydrogenated nitroxide (pages 3750–3757)

      Yohann Guillaneuf, Jean-Philippe Lamps, Jean-Marie Catala, Didier Gigmes and Eric Drockenmuller

      Version of Record online: 4 JUN 2012 | DOI: 10.1002/pola.26163

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      A tailor-made dialkylated linear nitroxide affords an excellent control of the bulk polymerization of styrene at 60 °C yielding well-defined polystyrenes with Mn up to 70,000 g mol−1. Interestingly, a rate of polymerization one order of magnitude higher than styrene thermal polymerization and depending on initial alkoxyamine concentration is observed. PREDICI modeling using experimentally obtained kinetic rate constants gives substantial information on the polymerization living character with respect to temperature and initial alkoxyamine concentration.

    7. Synthesis and Photovoltaic Properties of Thieno[3,4-c]pyrrole-4,6-dione-based donor–acceptor Copolymers (pages 3758–3766)

      Shanpeng Wen, Weidong Cheng, Pengfei Li, Shiyu Yao, Bin Xu, Hui Li, Yajun Gao, Zilong Wang and Wenjing Tian

      Version of Record online: 31 MAY 2012 | DOI: 10.1002/pola.26164

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      A series of novel 1,3-di(thien-2-yl)thieno[3,4-c]pyrrole-4,6-dione–based donor-acceptor polymers [(poly{9,9-dioctylfluorene-2,7-diyl-alt-1,3-bis(4-hexylthien-2-yl)-5-octylthieno [3,4-c]pyrrole-4,6-dione}, poly{N-(1-octylnonyl)carbazole-2,7-diyl-alt-1,3-bis(4-hexylthien-2-yl)-5-octylthieno[3,4-c]pyrrole-4,6-dione}, and poly{4,8-bis(2-ethylhexyloxyl) benzo[1,2-b:3,4-b′]dithiophene-alt-1,3-bis(4-hexylthien-2-yl)-5-octylthieno[3,4-c] pyrrole-4,6-dione} (PBDT-DTTPD)]PF-DTTPD, PC-DTTPD, and PBDT-DTTPD) consisting of different electron-rich donors in main-chains were synthesized. The PSC device containing the blend of donor PBDT-DTTPD and acceptor in 1:2 weight ratio showed the highest PCE value of 3.11% with Voc = 0.90 V, Jsc = 6.11 mA/cm2, and FF fill factor = 0.56.

    8. Metal- and solvent-free, clickable synthesis and postpolymerization functionalization of poly(triazole)s (pages 3767–3774)

      Fengyang Deng, Bin Xu, Yong Gao, Zheng Liu, Duanguang Yang and Huaming Li

      Version of Record online: 25 MAY 2012 | DOI: 10.1002/pola.26165

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      Linear poly(triazole)s (PTAs) were successfully synthesized by the metal- and solvent-free, thermal click polymerization of diazide and dialkyne monomers in an open atmosphere without protection from oxygen and moisture. The as-prepared polymer was further fractionated using a multi-step precipitation method, affording PTAs with well-defined architecture as evidenced by low polydispersity index (<1.30). Furthermore, the methyl benzoate moieties in the main chain can serve as useful building blocks for further postpolymerization functionalization, yielding 1,2,4-triazole derivatives. This functionalization strategy offers potential for the development of novel triazole-based materials.

    9. Hydrogen-bonded supramolecular polymers containing dimethylsilane groups: Synthesis, crystal structure, and characterization (pages 3775–3787)

      Mirela-Fernanda Zaltariov, Maria Cazacu, Sergiu Shova, Angelica Vlad, Iuliana Stoica and Elena Hamciuc

      Version of Record online: 25 MAY 2012 | DOI: 10.1002/pola.26166

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      A silicon-containing dicarboxylic acid, bis[N-(4-carboxyphenyl)phtalimidyl]dimethylsilane, was prepared and found to self-assemble through hydrogen bonds both itself and with bipyridyl derivatives in supramolecular polymers that show high residues at thermal decomposition in nitrogen atmosphere and glass transitions. Self-assembling was shown by FTIR and X-ray single-crystal diffraction. The ability for the structuration in film was emphasized by AFM and correlated with molecular transport capacity estimated by dynamic water vapor sorption analysis in dependence on temperature.

    10. Synthesis of novel side-chain triphenylamine polymers with azobenzene moieties via RAFT polymerization and investigation on their photoelectric properties (pages 3788–3796)

      Yan Sun, Nianchen Zhou, Wei Zhang, Yaowen Li, Zhenping Cheng, Jian Zhu, Zhengbiao Zhang and Xiulin Zhu

      Version of Record online: 31 MAY 2012 | DOI: 10.1002/pola.26167

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      Two well-defined polymers bearing triphenylamines incorporated to azobenzene units either directly or with an interval as pendant groups, PDMMA and PDPMMA, were successfully prepared via reversible addition-fragmentation chain transfer polymerization. The effect of photoisomerization of the azobenzene unit on the fluorescence emission, electrochemical behaviors and the hole mobility of these two polymers were apparent.

    11. Segmented block copolyesters using click chemistry (pages 3797–3805)

      Stephen M. June, Philippe Bissel and Timothy E. Long

      Version of Record online: 4 JUN 2012 | DOI: 10.1002/pola.26168

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      Click chemistry afforded the synthesis of triazole-containing polyesters and segmented copolyesters at moderate temperatures. Triazole-containing homopolyesters exhibited increased Tgs relative to structurally analogous homopolyesters synthesized using melt transesterification. The synthesis of telechelic azide-terminated poly(propylene glycol) and subsequent synthesis of triazole-containing segmented block copolyesters afforded polymers which melt pressed into ductile membranes with excellent thermomechanical response.

    12. Design, synthesis, photophysical, and electrochemical properties of DCM-based conjugated polymers for light-emitting devices (pages 3806–3818)

      Mahalingam Vanjinathan, Hong-Cheu Lin and A. Sultan Nasar

      Version of Record online: 4 JUN 2012 | DOI: 10.1002/pola.26169

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      A series of red-light-emitting conjugated hyperbranched polymers, hyperbranched copolymers, and linear polymers were synthesized. These polymers show excellent thermal stability and emit strong red photoluminescence (PL) around 566 nm–656 nm upon photo excitation. The results of photophysical, thermal, electrochemical studies, and electroluminescence (EL) devices reveal that these polymers are suitable candidates for application in polymer light-emitting diodes.

    13. Solvent-free polymerization of citric acid and hexamethylenediamine for novel carboxylated polyamides (pages 3819–3829)

      Man Jiang, Wei Chen, Ping Fang, Shangli Chen, Junxiao Bai, Yanfei Huang, Miaowei Han, Ping Lu and Jian Dong

      Version of Record online: 31 MAY 2012 | DOI: 10.1002/pola.26170

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      Copolymers of tributyl citrate and hexamethylenediamine were studied with a solvent-free condensation method. The reaction led to poly(succinimide-co-citramide) copolymers. Hydrolysis of the copolymers resulted in water soluble polycitramides structurally similar to biodegradable poly(aspartic acid)s. The polycitramides showed Ca and Pb ion chelating capabilities higher than poly(aspartic acid)s or citric acidsorbitol copolyesters and offer promise as a new class of metal sequesters.

    14. Synthesis and properties of hyperbranched poly(ether sulfone)s prepared by self-polycondensation of novel AB2 monomer (pages 3830–3839)

      Mitsutoshi Jikei, Daisuke Uchida, Yuuki Haruta, Yuuki Takahashi and Kazuya Matsumoto

      Version of Record online: 4 JUN 2012 | DOI: 10.1002/pola.26172

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      Hyperbranched poly(ether sulfone)s were prepared by the self-polycondensation of the novel AB2 monomer, 4-(3,5-hydroxyphenoxy)-4′-fluorodiphenylsulfone. The polymer having the degree of branching of 0.41 was prepared in the presence of cesium fluoride as a base. The solubility and the glass transition temperature of the polymers were influenced by the terminal functional groups. The unique thermal crosslinking phenomenon was observed for the hydroxyl-terminated hyperbranched poly(ether sulfone).

    15. Facile synthesis of nanoparticles via assembly of photopolymerized and self-crosslinked random copolymers in selective organic media (pages 3840–3847)

      Apiradee Honglawan, Lebo Xu and Shu Yang

      Version of Record online: 4 JUN 2012 | DOI: 10.1002/pola.26177

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      Photopolymerized and self-crosslinked random copolymers of poly(acryloyl chloride) are self-assembled into nanoparticles in a series of organic solvents. The size and morphology (spherical micelles vs. vesicles) of the assemblies can be controlled by the initial concentration of acrylic acid in the monomers, UV dosage, and solvent quality.

    16. Synthesis and photovoltaic properties of conjugated side chains polymers with different electron-withdrawing and donating end groups (pages 3848–3858)

      Zhaojie Gu, Lijun Deng, Hao Luo, Xia Guo, Haohao Li, Zhencai Cao, Xunshan Liu, Xinwei Li, Hongyan Huang, Yingzi Tan, Yong Pei and Songting Tan

      Version of Record online: 13 JUN 2012 | DOI: 10.1002/pola.26180

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      Four narrow band gap conjugated polymers composed of benzo[1,2-b:4,5-b′] dithiophene and thiophene with different conjugated side chains were synthesized and applied in bulk heterojunction solar cells.

    17. Poly(1-hexene) with long methylene sequences and controlled branches obtained by a thermostable α-diimine nickel catalyst with bulky camphyl backbone (pages 3859–3866)

      Fengshou Liu, Haiyang Gao, Zhilong Hu, Haibin Hu, Fangming Zhu and Qing Wu

      Version of Record online: 7 JUN 2012 | DOI: 10.1002/pola.26181

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      A bulky camphyl α-diimine catalyst can catalyze 1-hexene polymerization to produce PHs with a constant branching density (∼ 84/1000C) in the range of temperature from 0 to 80°C, and dominant methyl and butyl fraction can be tuned by varying polymerization temperatures. Long methylene sequences ([BOND](CH2) n[BOND], n > 20) are first observed in the PH materials.

    18. Living copolymerization of ethylene with norbornene by fluorinated enolato-imine titanium catalyst (pages 3867–3874)

      Andrea Ravasio, Laura Boggioni, Giulia Scalcione, Fabio Bertini, Daniele Piovani and Incoronata Tritto

      Version of Record online: 8 JUN 2012 | DOI: 10.1002/pola.26182

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      Complex [Ti(κ2-N,O-{2,6-F2C6H3N[DOUBLE BOND]C(Me)C(H) [DOUBLE BOND]C(CF3)O})2Cl2] (1) activated with d-MAO affords stereoirregular alternating high-molar-mass P(E-co-N)s with narrow molar mass distribution at temperatures between 25 and 90 °C. The living nature of E-co-N copolymerization at 50 °C was demonstrated by kinetics and synthesis of PE-block-P(E-co-N) as well as P(E-co-N)1-block-P(E-co-N)2, having different norbornene contents in the segments and different Tg values.

    19. Solution-processable and thermally cross-linkable fluorene-cored triple-triphenylamines with terminal vinyl groups to enhance electroluminescence of MEH-PPV: Synthesis, curing, and optoelectronic properties (pages 3875–3884)

      Chia-Shing Wu, Ya-Ju Yang, Szu-Wen Fang and Yun Chen

      Version of Record online: 7 JUN 2012 | DOI: 10.1002/pola.26184

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      A novel solution-processable and thermally cross-linkable fluorene-core with three periphery N-phenyl-N-(4-vinylphenyl)benzeneamines (FTV) was successfully synthesized as an electron- and hole-blocking material. Inserting cured-FTV between PEDOT:PSS and MEH-PPV to enhance the electroluminescence of MEH-PPV results in simultaneous reduction in hole injection from PEDOT:PSS to MEH-PPV and blocking in electron transport from MEH-PPV to anode. Current results demonstrate that the thermally cross-linkable FTV enhances not only device efficiency (0.27 cd/A [RIGHTWARDS ARROW]1.08 cd/A) but also film homogeneity after thermal curing. FTV is a promising electron- and hole-blocking material applicable for the fabrication of multilayer PLEDs based on PPV derivatives.

    20. Synthesis of double hydrophilic poly(ethylene oxide)-b-poly(2-hydroxyethyl acrylate) by single-electron transfer–living radical polymerization (pages 3885–3894)

      Erwan Nicol, Thibault Derouineau, Fanny Puaud and Andrii Zaitsev

      Version of Record online: 7 JUN 2012 | DOI: 10.1002/pola.26185

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      2-Hydroxyethyl acrylate (HEA) was polymerized by single-electron transfer–living radical polymerization (SET-LRP). The effects of both the ligand and the solvent on the polymerization were investigated. Hydrophilic homo-PHEA and double-hydrophilic PEO-b-PHEA block copolymers could be synthesized in both DMSO and pure water with a very good control over the chain length and the polydispersity index.

    21. Synthesis and characterization of electrophosphorescent jacketed conjugated polymers (pages 3895–3903)

      Wei Zhang, Hao Jin, Feng Zhou, Zhihao Shen, Dechun Zou and Xinghe Fan

      Version of Record online: 13 JUN 2012 | DOI: 10.1002/pola.26189

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      A series of electroluminescent jacketed conjugated polymers with different contents of oxadiazole moeity were successfully synthesized. The photophysical and electrochemical properties of the copolymers were characterized. The results show that the introduction of the oxidiazole-containing side chains into the polymer reduces the LUMO level. Electroluminescent devices were fabricated with a configuration of ITO/PEDOT:PSS/Sample/Ca/Al. All of the devices emit blue light. Then a cyclometalated iridium complex monomer (ppy)2Ir(BrPhPyBr) was copolymerized with PFOXD50 at different ratios. The devices with the same configuration emit orange light.

    22. Segmented polyurethane elastomers derived from aliphatic polycarbonate and poly(ester-carbonate) soft segments for biomedical applications (pages 3904–3913)

      Marcin Sobczak, Cezary Dębek, Ewa Olędzka, Grzegorz Nałęcz-Jawecki, Wacław L. Kołodziejski and Maria Rajkiewicz

      Version of Record online: 11 JUN 2012 | DOI: 10.1002/pola.26190

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      A series of polyols were synthesized by the ring-opening polymerization of ε-caprolactone, trimethylene carbonate, and neopentyl carbonate catalyzed by lipase from Candida Antarctica. Biomedical polyurethanes with improved hydrolytic stability were prepared by free-metal method from the polyols, 4,4′-methylenebis(phenyl isocyanate) and 1,4-butanediol. The received polyurethanes were not toxic to the test bionts, both bacteria and protozoans.

  4. Notes

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    2. Cover Image
    3. Rapid Communication
    4. Articles
    5. Notes
    6. Erratum
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      Synthesis and structure–property comparisons of hydrogenated poly(oxanorbornene-imide)s and poly(norbornene-imide)s prepared by ring-opening metathesis polymerization (pages 3914–3921)

      Kyung-Hwan Yoon, Kyung Oh Kim, Chengqing Wang, Insook Park and Do Y. Yoon

      Version of Record online: 7 JUN 2012 | DOI: 10.1002/pola.26171

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      Various structures of poly(norbornene-imide)s and poly(oxanorbornene-imide)s were synthesized and an optimal hydrogenation method was established. The thermal, thermomechanical, mechanical, and optical properties of thus prepared polymers were investigated, together with the structural characteristics shown by wide-angle X-ray scattering patterns. Poly(oxanorbornene-imide)s exhibit local nanostructure caused by intermolecular interactions between the imide and backbone oxygen moiety, which appears to prevent a significant decrease in Tg when compared with poly(norbornene-imide)s. Overall, hydrogenated poly(oxanorbornene-imide)s, obtained with more readily prepared exo-monomer, exhibit similar physical properties when compared with the corresponding hydrogenated poly(norbornene-imide)s.

  5. Erratum

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