Microwave-assisted Diels-Alder polycondensation of proton conducting poly(phenylene)s

被引:18
|
作者
Adamski, Michael [1 ]
Skalski, Thomas J. G. [1 ]
Xu, Shaoyi [1 ]
Killer, Miho [1 ]
Schibli, Eric M. [2 ]
Frisken, Barbara J. [2 ]
Holdcroft, Steven [1 ]
机构
[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
[2] Simon Fraser Univ, Dept Phys, Burnaby, BC V5A 1S6, Canada
基金
加拿大创新基金会; 加拿大自然科学与工程研究理事会;
关键词
POLYMER ELECTROLYTE MEMBRANES; SULFONATED AROMATIC POLYMERS; EXCHANGE MEMBRANES; FUEL-CELLS; ACID); DEGRADATION; COMBINATION; CONVERSION; COPOLYMERS; OXIDATION;
D O I
10.1039/c8py01804a
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
An exploratory microwave-assisted synthesis of a promising proton-conducting, Diels-Alder poly(phenylene) is reported and comprehensively compared against a traditional, thermal polymerization approach. A 24-fold reduction in reaction time is achieved by microwave synthesis. Characterization of polymers prepared by microwave-assisted synthesis vs. the thermal approach reveals little difference in their physicochemical and solid state electrochemical properties. However, membranes cast from polymers prepared by microwave synthesis possess a 7.0% increase in tensile strength but 38.6% lower elongation at break, which may be due to an increase in the number of para-para linkages found along the polymer backbone. High ex situ proton conductivities, up to 186 mS cm(-1) at 95% RH and 80 degrees C, are obtained for cast membranes. When assessed in situ as fuel cell membranes, the microwave-assisted polymer provided a similar maximum power density (1217 mW cm(-2)) to that prepared thermally (1206 mW cm(-2)). The consistency between the materials synthesized highlight the efficacy of microwave chemistry for rapid, scalable, and reproducible synthesis of advanced functional materials, such as proton-conducting Diels-Alder poly(phenylene)s.
引用
收藏
页码:1668 / 1685
页数:18
相关论文
共 50 条
  • [41] Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels-Alder Reaction with O-(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives
    Martin-Acosta, Pedro
    Feresin, Gabriela
    Tapia, Alejandro
    Estevez-Braun, Ana
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (20): : 9738 - 9756
  • [42] Microwave-assisted diels-alder reaction of 2H-pyran-2-ones with maleimides towards fused bicyclo[2.2.2]octenes
    Kranjc, Kristof
    Kocevar, Marijan
    HETEROCYCLES, 2007, 73 (01) : 481 - +
  • [43] GAMMA-ALUMINA ASSISTED DIELS-ALDER REACTION
    WALI, A
    SATISH, S
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1992, 31 (03): : 207 - 208
  • [44] Synthesis of 2-furfurylmaleimide and preliminary study of its Diels-Alder polycondensation
    Gousse, C
    Gandini, A
    POLYMER BULLETIN, 1998, 40 (4-5) : 389 - 394
  • [45] A short microwave-assisted synthesis of tetrahydroisoquinolin-pyrrolopyridinones by a triple process: Ugi-3CR-aza Diels-Alder/S-oxidation/Pummerer
    Islas-Jacome, Alejandro
    Gonzalez-Zamora, Eduardo
    Gamez-Montano, Rocio
    TETRAHEDRON LETTERS, 2011, 52 (41) : 5245 - 5248
  • [46] Synthesis of 2-furfurylmaleimide and preliminary study of its Diels-Alder polycondensation
    Gousse, C.
    Gandini, A.
    Polymer Bulletin (Berlin), 1998, 40 (4-5):
  • [47] Rapid Microwave-Assisted Chemical Recycling of Poly(p-Phenylene Terephthalamide)
    Benninga, Joel
    Gebben, Bert
    Folkersma, Rudy
    Voet, Vincent S. D.
    Loos, Katja
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2025, 147 (09) : 7191 - 7195
  • [48] Synthesis of 2-furfurylmaleimide and preliminary study of its Diels-Alder polycondensation
    Cecile Goussé
    Alessandro Gandini
    Polymer Bulletin, 1998, 40 : 389 - 394
  • [49] Ultra-Rapid Green Microwave Assisted Diels-Alder Reactions Using Ionic Liquid
    Rajendran, Annamalai
    Kumar, Ganesan Vinoth
    CURRENT MICROWAVE CHEMISTRY, 2016, 3 (01) : 55 - 59
  • [50] Recyclable organotungsten Lewis acid and microwave assisted Diels-Alder reactions in water and in ionic liquids
    Chen, IH
    Young, JN
    Yu, SJ
    TETRAHEDRON, 2004, 60 (51) : 11903 - 11909