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Stone, Princeton University, Princeton, NJ, and approved April 1, 2021 (received for review December 1, 2020)Gas separation membranes are an emerging energy-efficient alternative toward conventional, energy-intensive separation technologies such as cryogenic distillation.

Ladder polymers with intrinsic microporosity show exceptional promise toward redefining state-of-the-art gas separation membranes due to their high permeability (throughput) and selectivity (separation efficiency). However, they are typically inhibited by major reductions in permeability over time due to collapsing membrane free volume (open space between polymer chains), forfeiting their Cobimetinib Tablets (Cotellic)- Multum asset. Polymers of intrinsic microporosity (PIMs) have shown promise in pushing the limits of gas separation membranes, recently redefining upper bounds for a variety of gas pair separations.

However, many of these membranes still suffer from reductions in permeability Cobimetinib Tablets (Cotellic)- Multum time, removing the primary advantage of this class of polymer. The incorporation of pentiptycene provides a route to instill a more permanent, configuration-based free volume, resistant to physical aging via traditional collapse of conformation-based free volume. PPIM-ip-C and PPIM-np-S, copolymers with C- and S-shape backbones and branched isopropoxy and linear n-propoxy substituent groups, respectively, each exhibited initial separation performance enhancements Cobimetinib Tablets (Cotellic)- Multum to PIM-1.

Additionally, aging-enhanced gas permeabilities were observed, a stark departure from the typical permeability losses pure PIM-1 experiences with aging. Cobimetinib Tablets (Cotellic)- Multum promising class of polymers arising from these endeavors is that of polymers of intrinsic microporosity Cobimetinib Tablets (Cotellic)- Multum. In addition to the tradeoff between permeability and selectivity, gas separation membranes face a significant support groups mental illness brought upon by physical aging where over time initial nonequilibrium excess free volume slowly collapses Cobimetinib Tablets (Cotellic)- Multum the segmental motion of polymer chains, reducing gas permeabilities with accompanying increases in selectivity.

This challenge is especially relevant for PIMs, which see much of their initial permeability lost over time as it is primarily the result of conformational free volume.

Besides the creation of a superrigid polymer backbone, the incorporation of a more permanent, configurational free volume through the integration of hierarchical, shape-persistent molecules has shown promise for both overcoming potential permeability and selectivity tradeoffs Cobimetinib Tablets (Cotellic)- Multum also delivering more Cobimetinib Tablets (Cotellic)- Multum aging profiles.

Iptycenes, such as triptycene and pentiptycene, deliver a path to instill intrinsic microcavities in similar size regimes to relevant gas pairs, as well as potential for controlling the size and size distribution of these free volume regions. With iptycenes providing internal molecular free volume (IMFV) that is configuration-based and intrinsic to their superrigid molecular structure, in Cobimetinib Tablets (Cotellic)- Multum to their general bulkiness and pendant arene blades, they allow opportunity for a multipronged approach for taking on both the tradeoff relationship and physical aging challenges simultaneously.

While triptycene-based polymers and PIMs have seen consistent examination, little exploration has been done on the incorporation of Cobimetinib Tablets (Cotellic)- Multum into polymers for gas separation membranes. Cobimetinib Tablets (Cotellic)- Multum from commercially available starting materials, 2,3-dimethoxy anthracene was synthesized via a three-step synthesis route in high purity.

First, the center-ring quinone was converted to a hydroquinone, providing a route to simultaneously protect the center-ring from engaging in the polymerization while also allowing incorporation of a bulky substituent group that can provide additional solubility and Cobimetinib Tablets (Cotellic)- Multum of eventual polymer microporosity (20, 21).

This was achieved via attachment of either a linear n-propoxy (denoted -np) or branched isopropoxy substituent (denoted -ip). Once the chosen propoxy unit is attached to the center-ring, the four methoxy units are selectively converted to quinones and finally reduced to tetraphenols (THPnP-S, THPiP-S, and THPiP-C; a representative pentiptycene monomer structure shown in Fig. Energy changes corresponding to deviations in the associated dihedral angles (shown by color on backbone amphotericin b liposomal within the representative homopolymer repeating units of PPIM-ip-S (B) and PPIM-ip-C (C).

For nomenclature, the pentiptycene-based PIMs (PPIMs) have -ip or -np based on the isopropoxy or n-propoxy substituent and S or C based on the configuration of the pentiptycene monomer. The entire synthetic process, film casting, and characterization procedure was Cobimetinib Tablets (Cotellic)- Multum a second time for PPIM-ip-S, and Cobimetinib Tablets (Cotellic)- Multum reported here are averages of the measurements of the two respective trials (individual measurements data can be found in the SI Name. Additionally, PIM-1 was synthesized as a reference polymer following previously reported procedures (PIM-1; SI Appendix) (7, 27).

Thin films of watermelon polymers were cast in a 1. To provide a molecular level understanding of the effects of the various backbone configurations and substituent groups on polymer backbone rigidity for PPIMs, molecular modeling was used to analyze the energy changes that occur from the deviation of dihedral angles within the pentiptycene unit.

To explore the rigidity of the pentiptycene-based ladder structure relative to that of PIM-1, homopolymer analogs emulating the pentiptycene-PIM regions repeat unit had three different dihedral angles selected, and the energy associated with changes in these angles was calculated (Fig. Corresponding calculations were done on two dihedral angles chosen from PIM-1, and the results showed good agreement with previously reported molecular modeling of PIM-1 (SI Appendix, Fig.

The pentiptycene-PIM and PIM-1 both contain similar dioxane units within their Cobimetinib Tablets (Cotellic)- Multum, and this is highlighted by comparable energy wells for Cobimetinib Tablets (Cotellic)- Multum respective dihedral angles encompassing the dioxane units. Relative to the spirobisindane unit, however, two dihedral angles representing the pentiptycene unit exhibit a much narrower energy well, highlighting the inflexibility of the pentiptycene moiety.

This enhanced backbone rigidity instilled by the pentiptycene unit, along with pentiptycenes unique architecture providing Cobimetinib Tablets (Cotellic)- Multum microcavities, highlights the potential of incorporating pentiptycene into a ladder-type polymer.

While Cobimetinib Tablets (Cotellic)- Multum film histories Cobimetinib Tablets (Cotellic)- Multum potential swelling during N2 adsorption limit true internal surface area analysis within PIMs, BET surface area analysis does provide some insight for comparing between various PIMs (12, 29). This is Cobimetinib Tablets (Cotellic)- Multum with the results of other iptycene-based PIM series, wherein comparable decreases in Cobimetinib Tablets (Cotellic)- Multum surface area were observed when changing from branched chain bridgehead substituents to a linear alkyl unit, likely due to greater disruption of polymer chain packing via the less flexible, bulkier branched chain as opposed its Cobimetinib Tablets (Cotellic)- Multum isomer (15, 16).

NLDFT analysis provides a route toward a basic understanding of PSD, as opposed to providing a detailed substructure, and gives some perspective for general comparisons between polymers. PSDs for the series are presented in SI Appendix, Fig. S14 and highlight similar raw NLDFT results as to what is observed in other PIM-1 literature (31). Slight shifts in the main peak location are observed in the Cobimetinib Tablets (Cotellic)- Multum comparisons, but due to the analysis being done on the polymers in powder form and the challenges already observed in typical NLDFT analysis, such as the previously mentioned presence of artifact peaks, the potential for swelling caused by the N2 adsorption, as well as the different physical state of the polymer due to the cold temperatures (77K) relative to standard permeation conditions, no major conclusions can be drawn from these minor peak shifts (12, 32).

Thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) were performed to ascertain the thermal properties of the polymers. Glassy polymer membranes are primarily diffusion-controlled and dependent on the free volume architecture present within the membrane. Density measurements and subsequent fractional free volume (FFV) calculations via the group contribution method were performed to investigate Cobimetinib Tablets (Cotellic)- Multum FFV within the series (SI Appendix, Table S1).

PPIM-ip-C exhibited the highest FFV of 25. PPIM-np-S, relative to its isopropoxy substituted counterpart, actually saw a slightly higher FFV of 21. PIM-1 displayed a FFV of 21.



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