Design and Synthesis of Polyimides Based on Carbocyclic Pseudo-Tröger’s Base-Derived Dianhydrides for Membrane Gas Separation Applications

Abstract

dianhydride (CTB2), were made and used for the synthesis of soluble polyimides of intrinsic microporosity with 3,3′-dimethylnaphthidine (DMN). The polyimides CTB1-DMN and CTB2-DMN exhibited excellent thermal stability of ∼500 °C and high BET surface areas of 580 and 469 m 2 g −1 , respectively. A freshly made dione-substituted CTB2-DMN membrane demonstrated promising gas separation performance with O 2 permeability of 206 barrer and O 2 /N 2 selectivity of 5.2. A higher O 2 permeability of 320 barrer and lower O 2 /N 2 selectivity of 4.2 were observed for a fresh CTB1-DMN film due to its higher surface area and less tightly packed structure as indicated by weaker charge-transfer complex interactions. Physical aging over 60 days resulted in reduction in gas permeability and moderately enhanced selectivity. CTB2-DMN exhibited notable performance with gas permeation data located between the 2008 and 2015 permeability/selectivity upper bounds for O 2 /N 2 and H 2 /CH 4 .

Prospects of Membrane Science Development

“…The treatment with lower alcohols (methanol and ethanol) leads to a noticeable growth in gas permeability, often without a loss of selectivity [10,12]. Like disubstituted polyacetylenes, they show propensity to physical aging, i.e., a decrease in gas permeability over time [14]. Recently, approaches to overcome this undesirable effect have been under development [15].…”

Green facile fabrication of polyimide by microwave‐assisted hydrothermal method and its decomposition dynamics

“…[1][2][3][4] In general, aromatic polyimides are usually obtained by imidizing the aromatic poly(amic acid) precursors, which were obtained from anhydride monomers and amine monomers. [1][2][3][4] In general, aromatic polyimides are usually obtained by imidizing the aromatic poly(amic acid) precursors, which were obtained from anhydride monomers and amine monomers.…”

“…Aromatic polyimides, a class of high-performance polymers containing large amounts of imide and aromatic rings, have attracted significant interests and bring about wide range of applications in the high-tech fields because of their advanced properties in thermal aging and thermal and chemical stability. [1][2][3][4] In general, aromatic polyimides are usually obtained by imidizing the aromatic poly(amic acid) precursors, which were obtained from anhydride monomers and amine monomers. 5,6 The whole process is carried out in toxic solvents, such as cresols, N,N-dimethylformamide, and N,N-dimethylacetamide, 7,8 which is not friendly to the environment.…”

Investigation of thermal and fluorescent properties of benzoxazole-linked triphenylamine-based co-polyimides

“…Aromatic polyimides is a well-known class of high-performance materials because of their outstanding properties 1 –3 and find numerous industrial applications such as dielectric films, photoresists 4 –6 membranes for gas separation, 7 matrices for high-temperature application, 8 in the field of adhesive, 9 automobile, aerospace, 10 and fuel cells. 9 –11 Among optoelectronic device applications, polyimides have attracted tremendous attention such as light-emitting diodes, memory devices, electrochromic devices, and photovoltaics.…”