Diacetylenes with Ionic-Liquid-Like Substituents: Associating a Polymerizing Cation with a Polymerizing Anion in a Single Precursor for the Synthesis of N-Doped Carbon Materials
Imidazolium‐ and benzimidazolium‐substituted diacetylenes with bromide or nitrogen‐rich dicyanamide and tricyanomethanide anions were synthesized and used as precursors for the preparation of N‐doped carbon materials. On pyrolysis under argon at 800 °C both halide precursors afforded graphite‐like s...
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Published in | Chemistry : a European journal Vol. 22; no. 5; pp. 1682 - 1695 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
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Blackwell Publishing Ltd
26.01.2016
Wiley Wiley Subscription Services, Inc Wiley-VCH Verlag |
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Abstract | Imidazolium‐ and benzimidazolium‐substituted diacetylenes with bromide or nitrogen‐rich dicyanamide and tricyanomethanide anions were synthesized and used as precursors for the preparation of N‐doped carbon materials. On pyrolysis under argon at 800 °C both halide precursors afforded graphite‐like structures with nitrogen contents of about 8.5 %. When the dicyanamide and tricyanomethanide precursors were thermolyzed at the same temperature, graphite‐like structures were obtained that exhibit nitrogen contents in the range 17–20 wt %; thereby, the benefit of associating a polymerizing cation with a polymerizing anion in a single precursor was demonstrated. On pyrolysis at 1100 °C the nitrogen contents of the latter pyrolysates remain high (ca. 6 wt %). Adsorption measurements with krypton at 77 K indicated that the materials are nonporous. The highest electrical conductivity was observed for a pyrolysate with one of the lowest nitrogen contents, which also has the highest degree of graphitization. Thus, the quest for N‐rich carbons with high electrical conductivities should include both maximization of the nitrogen content and optimization of the degree of graphitization. Crystallographic investigation of the precursors and spectroscopic characterization of the pyrolysates prepared by heating at 220 °C indicate that construction of the final carbon framework does not involve the intermediate formation of a polydiacetylene.
N‐riched carbon: Azolium‐substituted diacetylenic compounds with nitrogen‐rich dicyanamide and tricyanomethanide anions undergo concomitant trimerization of the anions and polycyclization of the diacetylenic units to produce graphite‐like carbon materials (see figure). Nitrogen contents reach 17–20 wt % at 800 °C and remain as high as about 6 wt % at 1100 °C. |
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AbstractList | Imidazolium- and benzimidazolium-substituted diacetylenes with bromide or nitrogen-rich dicyanamide and tricyanomethanide anions were synthesized and used as precursors for the preparation of N-doped carbon materials. On pyrolysis under argon at 800 °C both halide precursors afforded graphite-like structures with nitrogen contents of about 8.5%. When the dicyanamide and tricyanomethanide precursors were thermolyzed at the same temperature, graphite-like structures were obtained that exhibit nitrogen contents in the range 17-20 wt%; thereby, the benefit of associating a polymerizing cation with a polymerizing anion in a single precursor was demonstrated. On pyrolysis at 1100 °C the nitrogen contents of the latter pyrolysates remain high (ca. 6 wt%). Adsorption measurements with krypton at 77 K indicated that the materials are nonporous. The highest electrical conductivity was observed for a pyrolysate with one of the lowest nitrogen contents, which also has the highest degree of graphitization. Thus, the quest for N-rich carbons with high electrical conductivities should include both maximization of the nitrogen content and optimization of the degree of graphitization. Crystallographic investigation of the precursors and spectroscopic characterization of the pyrolysates prepared by heating at 220 °C indicate that construction of the final carbon framework does not involve the intermediate formation of a polydiacetylene. Imidazolium- and benzimidazolium-substituted diacetylenes with bromide or nitrogen-rich dicyanamide and tricyanomethanide anions were synthesized and used as precursors for the preparation of N-doped carbon materials. On pyrolysis under argon at 800°C both halide precursors afforded graphite-like structures with nitrogen contents of about 8.5%. When the dicyanamide and tricyanomethanide precursors were thermolyzed at the same temperature, graphite-like structures were obtained that exhibit nitrogen contents in the range 17-20wt%; thereby, the benefit of associating a polymerizing cation with a polymerizing anion in a single precursor was demonstrated. On pyrolysis at 1100°C the nitrogen contents of the latter pyrolysates remain high (ca. 6wt%). Adsorption measurements with krypton at 77K indicated that the materials are nonporous. The highest electrical conductivity was observed for a pyrolysate with one of the lowest nitrogen contents, which also has the highest degree of graphitization. Thus, the quest for N-rich carbons with high electrical conductivities should include both maximization of the nitrogen content and optimization of the degree of graphitization. Crystallographic investigation of the precursors and spectroscopic characterization of the pyrolysates prepared by heating at 220°C indicate that construction of the final carbon framework does not involve the intermediate formation of a polydiacetylene. Abstract Imidazolium‐ and benzimidazolium‐substituted diacetylenes with bromide or nitrogen‐rich dicyanamide and tricyanomethanide anions were synthesized and used as precursors for the preparation of N‐doped carbon materials. On pyrolysis under argon at 800 °C both halide precursors afforded graphite‐like structures with nitrogen contents of about 8.5 %. When the dicyanamide and tricyanomethanide precursors were thermolyzed at the same temperature, graphite‐like structures were obtained that exhibit nitrogen contents in the range 17–20 wt %; thereby, the benefit of associating a polymerizing cation with a polymerizing anion in a single precursor was demonstrated. On pyrolysis at 1100 °C the nitrogen contents of the latter pyrolysates remain high (ca. 6 wt %). Adsorption measurements with krypton at 77 K indicated that the materials are nonporous. The highest electrical conductivity was observed for a pyrolysate with one of the lowest nitrogen contents, which also has the highest degree of graphitization. Thus, the quest for N‐rich carbons with high electrical conductivities should include both maximization of the nitrogen content and optimization of the degree of graphitization. Crystallographic investigation of the precursors and spectroscopic characterization of the pyrolysates prepared by heating at 220 °C indicate that construction of the final carbon framework does not involve the intermediate formation of a polydiacetylene. Imidazolium- and benzimidazolium-substituted diacetylenes with bromide or nitrogen-rich dicyanamide and tricyanomethanide anions were synthesized and used as precursors for the preparation of N-doped carbon materials. On pyrolysis under argon at 800 degree C both halide precursors afforded graphite-like structures with nitrogen contents of about 8.5%. When the dicyanamide and tricyanomethanide precursors were thermolyzed at the same temperature, graphite-like structures were obtained that exhibit nitrogen contents in the range 17-20wt%; thereby, the benefit of associating a polymerizing cation with a polymerizing anion in a single precursor was demonstrated. On pyrolysis at 1100 degree C the nitrogen contents of the latter pyrolysates remain high (ca. 6wt%). Adsorption measurements with krypton at 77K indicated that the materials are nonporous. The highest electrical conductivity was observed for a pyrolysate with one of the lowest nitrogen contents, which also has the highest degree of graphitization. Thus, the quest for N-rich carbons with high electrical conductivities should include both maximization of the nitrogen content and optimization of the degree of graphitization. Crystallographic investigation of the precursors and spectroscopic characterization of the pyrolysates prepared by heating at 220 degree C indicate that construction of the final carbon framework does not involve the intermediate formation of a polydiacetylene. N-riched carbon: Azolium-substituted diacetylenic compounds with nitrogen-rich dicyanamide and tricyanomethanide anions undergo concomitant trimerization of the anions and polycyclization of the diacetylenic units to produce graphite-like carbon materials (see figure). Nitrogen contents reach 17-20wt% at 800 degree C and remain as high as about 6wt% at 1100 degree C. Imidazolium- and benzimidazolium-substituted diacetylenes with bromide or nitrogen-rich dicyanamide and tricyanomethanide anions were synthesized and used as precursors for the preparation of N-doped carbon materials. On pyrolysis under argon at 800 degrees C both halide precursors afforded graphite-like structures with nitrogen contents of about 8.5 %. When the dicyanamide and tricyanomethanide precursors were thermolyzed at the same temperature, graphite-like structures were obtained that exhibit nitrogen contents in the range 17-20 wt%; thereby, the benefit of associating a polymerizing cation with a polymerizing anion in a single precursor was demonstrated. On pyrolysis at 1100 degrees C the nitrogen contents of the latter pyrolysates remain high (ca. 6 wt%). Adsorption measurements with krypton at 77 K indicated that the materials are nonporous. The highest electrical conductivity was observed for a pyrolysate with one of the lowest nitrogen contents, which also has the highest degree of graphitization. Thus, the quest for N-rich carbons with high electrical conductivities should include both maximization of the nitrogen content and optimization of the degree of graphitization. Crystallographic investigation of the precursors and spectroscopic characterization of the pyrolysates prepared by heating at 220 degrees C indicate that construction of the final carbon framework does not involve the intermediate formation of a polydiacetylene. Imidazolium‐ and benzimidazolium‐substituted diacetylenes with bromide or nitrogen‐rich dicyanamide and tricyanomethanide anions were synthesized and used as precursors for the preparation of N‐doped carbon materials. On pyrolysis under argon at 800 °C both halide precursors afforded graphite‐like structures with nitrogen contents of about 8.5 %. When the dicyanamide and tricyanomethanide precursors were thermolyzed at the same temperature, graphite‐like structures were obtained that exhibit nitrogen contents in the range 17–20 wt %; thereby, the benefit of associating a polymerizing cation with a polymerizing anion in a single precursor was demonstrated. On pyrolysis at 1100 °C the nitrogen contents of the latter pyrolysates remain high (ca. 6 wt %). Adsorption measurements with krypton at 77 K indicated that the materials are nonporous. The highest electrical conductivity was observed for a pyrolysate with one of the lowest nitrogen contents, which also has the highest degree of graphitization. Thus, the quest for N‐rich carbons with high electrical conductivities should include both maximization of the nitrogen content and optimization of the degree of graphitization. Crystallographic investigation of the precursors and spectroscopic characterization of the pyrolysates prepared by heating at 220 °C indicate that construction of the final carbon framework does not involve the intermediate formation of a polydiacetylene. N‐riched carbon: Azolium‐substituted diacetylenic compounds with nitrogen‐rich dicyanamide and tricyanomethanide anions undergo concomitant trimerization of the anions and polycyclization of the diacetylenic units to produce graphite‐like carbon materials (see figure). Nitrogen contents reach 17–20 wt % at 800 °C and remain as high as about 6 wt % at 1100 °C. |
Author | Vioux, André van der Lee, Arie Dutremez, Sylvain G. Dumail, Xavier Viau , Lydie Fahsi, Karim |
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Keywords | POLYYNES alkynes cyanides REACTIVITY CRYSTAL-STRUCTURES GRAPHITE SALTS nitrogen doping SOLID-STATE azolium compounds SPECTROSCOPY carbon NITROGEN DERIVATIVES CYCLOAROMATIZATION |
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Snippet | Imidazolium‐ and benzimidazolium‐substituted diacetylenes with bromide or nitrogen‐rich dicyanamide and tricyanomethanide anions were synthesized and used as... Imidazolium- and benzimidazolium-substituted diacetylenes with bromide or nitrogen-rich dicyanamide and tricyanomethanide anions were synthesized and used as... Abstract Imidazolium‐ and benzimidazolium‐substituted diacetylenes with bromide or nitrogen‐rich dicyanamide and tricyanomethanide anions were synthesized and... |
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SubjectTerms | Adsorption alkynes Anions Argon azolium compounds Carbon Cationic polymerization Chemical Sciences Chemical synthesis Chemistry Chemistry, Multidisciplinary Conductivity Construction Crystallography cyanides Electrical conductivity Electrical resistivity Graphite Graphitization Heating Ionic liquids Krypton Material chemistry Maximization Nitrogen nitrogen doping Optimization Physical Sciences Polydiacetylenes Polymerization Precursors Pyrolysis Resistivity Science & Technology Spectroscopy Temperature effects |
Title | Diacetylenes with Ionic-Liquid-Like Substituents: Associating a Polymerizing Cation with a Polymerizing Anion in a Single Precursor for the Synthesis of N-Doped Carbon Materials |
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