Synthesis and characterization of novel triptycene dianhydrides and polyimides of intrinsic microporosity based on 3,3ʹ-dimethylnaphthidine

Bader Ghanem, Fahd Alghunaimi, Xiaohua Ma, Nasser Y. Alaslai, Ingo Pinnau

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44 Scopus citations


Two intrinsically microporous polyimides were obtained by high-temperature, one-pot poly-condensation reaction of novel triptycene-based dianhydrides containing dimethyl- or diisopropyl-bridgehead groups with a commercially available highly sterically hindered 3,3 '-dimethylnaphthidine (DMN) diamine monomer. The dimethyl bridgehead groups in the triptycene building block provided the DMN-based polyimide (TDA1-DMN) with larger surface area (760 m(2) g(-1)) than the diisopropyl-based polyimide (TDA1-DMN) (680 m(2) g(-1)), greater fraction of ultramicroporosity, as observed from N-2 and CO2 NLDFT adsorption analysis, and higher gas permeability and selectivity. Wide-angle X-ray diffraction (WAXD) measurements demonstrated that TDA1-DMN and TDAi3-DMN exhibited a bimodal pore size distribution, where TDA1-DMN showed smaller d-spacing values and broader intensity peaks. Both TDADMN-based polyimides showed very high gas permeabilities with moderate selectivities. For example, fresh TDA1-DMN exhibited an O-2 permeability of 783 Barrer coupled with an O-2/N-2 selectivity of 4.3 and H-2 permeability of 3050 Barrer with H-2/N-2 selectivity of 16.7, values that surpassed the 2008 Robeson permeability/selectivity upper bounds. Physical aging of the TDA-DMN polyimide films over a period of 250 days showed relatively small changes in permeability (similar to 20%) and selectivity (similar to 5%). (C) 2016 Elsevier Ltd. All rights reserved.
Original languageEnglish (US)
Pages (from-to)225-232
Number of pages8
StatePublished - Aug 29 2016

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: The research reported in this publication was supported by funding from King Abdullah University of Science and Technology (KAUST). The authors would like to thank Dr. Kexin Yao for providing melting point characterization of the intermediate compounds.


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