Facile Synthesis of a Hydroxyl-Functionalized Tröger’s Base Diamine: A New Building Block for High-Performance Polyimide Gas Separation Membranes | Zendy

Xiaohua Ma | Zendy; Mahmoud A. Abdulhamid | Zendy; Xiaohe Miao | Zendy; Ingo Pinnau | Zendy

Open Access

Facile Synthesis of a Hydroxyl-Functionalized Tröger’s Base Diamine: A New Building Block for High-Performance Polyimide Gas Separation Membranes

Author(s) -

Xiaohua Ma,

Mahmoud A. Abdulhamid,

Xiaohe Miao,

Ingo Pinnau

Publication year - 2017

Publication title -

macromolecules

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.994

H-Index - 313

eISSN - 1520-5835

pISSN - 0024-9297

DOI - 10.1021/acs.macromol.7b02301

Subject(s) - diamine , selectivity , polyimide , polymer chemistry , amine gas treating , membrane , materials science , barrer , gas separation , thermal stability , microporous material , thermal decomposition , condensation polymer , chemistry , chemical engineering , polymer , organic chemistry , catalysis , biochemistry , layer (electronics) , engineering

Two intrinsically microporous polyimides (PIM-PIs) were synthesized by the polycondensation reaction of 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) and 3,3,3′,3′-tetramethylspirobisindane-6,7,6′,7′-tetracarboxylic dianhydride (SBI) with a newly designed o-hydroxyl-functionalized Tröger’s base diamine, 1,7-diamino-6H,12H-5,11-methanodibenzo[1,5]diazocine-2,8-diol (HTB). Both amorphous PIM-PIs were soluble in aprotic solvents and showed excellent thermal stability with onset decomposition temperature of ∼380 °C. SBI-HTB displayed a higher CO2 permeability (466 vs 67 barrer) than 6FDA-HTB but a significantly lower selectivity for CO2/CH4 (29 vs 73), H2/CH4 (29 vs 181), O2/N2 (4.6 vs 6.0), and N2/CH4 (1 vs 2.5). 6FDA-HTB displayed the highest gas-pair permselectivity values of all reported OH-functionalized PIM-PIs to date. The high permselectivity of 6FDA-HTB resulted primarily from exceptional diffusion selectivity due to strong size-sieving properties caused by hydrogen bonding between the proton of the hydroxyl group and the nitrogen atoms in the tertiary amine of the Tröger’s base (O–H···N)

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