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Synthesis and Gas-Permeation Characterization of a Novel High-Surface Area Polyamide Derived from 1,3,6,8-Tetramethyl-2,7-diaminotriptycene: Towards Polyamides of Intrinsic Microporosity (PIM-PAs)

A triptycene-based diamine, 1,3,6,8-tetramethyl-2,7-diamino-triptycene (TMDAT), was used for the synthesis of a novel solution-processable polyamide obtained via polycondensation reaction with 4,4′-(hexafluoroisopropylidene)bis(benzoic acid) (6FBBA). Molecular simulations confirmed that the tetrasub...

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Autores principales: Genduso, Giuseppe, Ghanem, Bader S., Wang, Yingge, Pinnau, Ingo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6419219/
https://www.ncbi.nlm.nih.gov/pubmed/30960345
http://dx.doi.org/10.3390/polym11020361
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author Genduso, Giuseppe
Ghanem, Bader S.
Wang, Yingge
Pinnau, Ingo
author_facet Genduso, Giuseppe
Ghanem, Bader S.
Wang, Yingge
Pinnau, Ingo
author_sort Genduso, Giuseppe
collection PubMed
description A triptycene-based diamine, 1,3,6,8-tetramethyl-2,7-diamino-triptycene (TMDAT), was used for the synthesis of a novel solution-processable polyamide obtained via polycondensation reaction with 4,4′-(hexafluoroisopropylidene)bis(benzoic acid) (6FBBA). Molecular simulations confirmed that the tetrasubstitution with ortho-methyl groups in the triptycene building block reduced rotations around the C–N bond of the amide group leading to enhanced fractional free volume. Based on N(2) sorption at 77 K, 6FBBA-TMDAT revealed microporosity with a Brunauer–Emmett–Teller (BET) surface area of 396 m(2) g(−1); to date, this is the highest value reported for a linear polyamide. The aged 6FBBA-TMDAT sample showed moderate pure-gas permeabilities (e.g., 198 barrer for H(2), ~109 for CO(2), and ~25 for O(2)) and permselectivities (e.g., αH(2)/CH(4) of ~50) that position this polyamide close to the 2008 H(2)/CH(4) and H(2)/N(2) upper bounds. CO(2)–CH(4) mixed-gas permeability experiments at 35 °C demonstrated poor plasticization resistance; mixed-gas permselectivity negatively deviated from the pure-gas values likely, due to the enhancement of CH(4) diffusion induced by mixing effects.
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spelling pubmed-64192192019-04-02 Synthesis and Gas-Permeation Characterization of a Novel High-Surface Area Polyamide Derived from 1,3,6,8-Tetramethyl-2,7-diaminotriptycene: Towards Polyamides of Intrinsic Microporosity (PIM-PAs) Genduso, Giuseppe Ghanem, Bader S. Wang, Yingge Pinnau, Ingo Polymers (Basel) Article A triptycene-based diamine, 1,3,6,8-tetramethyl-2,7-diamino-triptycene (TMDAT), was used for the synthesis of a novel solution-processable polyamide obtained via polycondensation reaction with 4,4′-(hexafluoroisopropylidene)bis(benzoic acid) (6FBBA). Molecular simulations confirmed that the tetrasubstitution with ortho-methyl groups in the triptycene building block reduced rotations around the C–N bond of the amide group leading to enhanced fractional free volume. Based on N(2) sorption at 77 K, 6FBBA-TMDAT revealed microporosity with a Brunauer–Emmett–Teller (BET) surface area of 396 m(2) g(−1); to date, this is the highest value reported for a linear polyamide. The aged 6FBBA-TMDAT sample showed moderate pure-gas permeabilities (e.g., 198 barrer for H(2), ~109 for CO(2), and ~25 for O(2)) and permselectivities (e.g., αH(2)/CH(4) of ~50) that position this polyamide close to the 2008 H(2)/CH(4) and H(2)/N(2) upper bounds. CO(2)–CH(4) mixed-gas permeability experiments at 35 °C demonstrated poor plasticization resistance; mixed-gas permselectivity negatively deviated from the pure-gas values likely, due to the enhancement of CH(4) diffusion induced by mixing effects. MDPI 2019-02-19 /pmc/articles/PMC6419219/ /pubmed/30960345 http://dx.doi.org/10.3390/polym11020361 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Genduso, Giuseppe
Ghanem, Bader S.
Wang, Yingge
Pinnau, Ingo
Synthesis and Gas-Permeation Characterization of a Novel High-Surface Area Polyamide Derived from 1,3,6,8-Tetramethyl-2,7-diaminotriptycene: Towards Polyamides of Intrinsic Microporosity (PIM-PAs)
title Synthesis and Gas-Permeation Characterization of a Novel High-Surface Area Polyamide Derived from 1,3,6,8-Tetramethyl-2,7-diaminotriptycene: Towards Polyamides of Intrinsic Microporosity (PIM-PAs)
title_full Synthesis and Gas-Permeation Characterization of a Novel High-Surface Area Polyamide Derived from 1,3,6,8-Tetramethyl-2,7-diaminotriptycene: Towards Polyamides of Intrinsic Microporosity (PIM-PAs)
title_fullStr Synthesis and Gas-Permeation Characterization of a Novel High-Surface Area Polyamide Derived from 1,3,6,8-Tetramethyl-2,7-diaminotriptycene: Towards Polyamides of Intrinsic Microporosity (PIM-PAs)
title_full_unstemmed Synthesis and Gas-Permeation Characterization of a Novel High-Surface Area Polyamide Derived from 1,3,6,8-Tetramethyl-2,7-diaminotriptycene: Towards Polyamides of Intrinsic Microporosity (PIM-PAs)
title_short Synthesis and Gas-Permeation Characterization of a Novel High-Surface Area Polyamide Derived from 1,3,6,8-Tetramethyl-2,7-diaminotriptycene: Towards Polyamides of Intrinsic Microporosity (PIM-PAs)
title_sort synthesis and gas-permeation characterization of a novel high-surface area polyamide derived from 1,3,6,8-tetramethyl-2,7-diaminotriptycene: towards polyamides of intrinsic microporosity (pim-pas)
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6419219/
https://www.ncbi.nlm.nih.gov/pubmed/30960345
http://dx.doi.org/10.3390/polym11020361
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