Dibenzomethanopentacene‐Based Polymers of Intrinsic Microporosity for Use in Gas‐Separation Membranes

• Published in: Angewandte Chemie International Edition Vol. 62; no. 8; pp. e202215250 - n/a
• Main Authors: Chen, Jie, Longo, Mariagiulia, Fuoco, Alessio, Esposito, Elisa, Monteleone, Marcello, Comesaña Gándara, Bibiana, Carolus Jansen, Johannes, McKeown, Neil B.
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 13.02.2023; John Wiley and Sons Inc
• Edition: International ed. in English
• Subjects: Ageing; Dibenzomethanopentacene; Diels-Alder reactions; Fabrication; Gas Separation; Membranes; Microporosity; Monomers; Permeability; Polymers; Polymers of Intrinsic Microporosity; Selectivity; Upper bounds; Membranes; Dibenzomethanopentacene; Gas Separation; Ageing; Polymers of Intrinsic Microporosity
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.202215250

Dibenzomethanopentacene (DBMP) is shown to be a useful structural component for making Polymers of Intrinsic Microporosity (PIMs) with promise for making efficient membranes for gas separations. DBMP‐based monomers for PIMs are readily prepared using a Diels–Alder reaction between 2,3‐dimethoxyanthracene and norbornadiene as the key synthetic step. Compared to date for the archetypal PIM‐1, the incorporation of DBMP simultaneously enhances both gas permeability and the ideal selectivity for one gas over another. Hence, both ideal and mixed gas permeability data for DBMP‐rich co‐polymers and an amidoxime modified PIM are close to the current Robeson upper bounds, which define the state‐of‐the‐art for the trade‐off between permeability and selectivity, for several important gas pairs. Furthermore, long‐term studies (over ≈3 years) reveal that the reduction in gas permeabilities on ageing is less for DBMP‐containing PIMs relative to that for other high performing PIMs, which is an attractive property for the fabrication of membranes for efficient gas separations. A series of dibenzomethanopentacene (DBMP) containing polymers of intrinsic microporosity (PIMs) were synthesised showing both high performance for pure and mixed gas permeability/selectivity and reduced ageing. The data for DBMP‐rich PIMs are close to the latest Robeson upper bounds for several important gas pairs indicating their potential for making gas separation membranes.