Design of enhanced porous organic cage solubility in Type 2 porous liquids

Rimsza, Jessica; Nenoff, Tina M.

doi:10.1016/j.molliq.2023.121536

Design of enhanced porous organic cage solubility in Type 2 porous liquids

Journal Article · Sat Feb 25 23:00:00 EST 2023 · Journal of Molecular Liquids

DOI:https://doi.org/10.1016/j.molliq.2023.121536· OSTI ID:2311571

Rimsza, Jessica ^[1]; Nenoff, Tina M. ^[1]

Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)

Decreasing cost of technologies for direct air capture of carbon can be achieved through the design of new materials with high CO₂ selectivity that can be incorporated into existing industrial processes. An emerging class of materials for these applications are porous liquids (PLs). PLs are mixtures of porous hosts and solvents with intrinsic porosity due to steric exclusion of solvent from inside the porous host. It is currently unknown how solvent -porous host interactions affect porous host solubility in the bulk solvent. Here, in this study, density functional theory simulations were used to investigate interactions between nine solvents and a CC13 porous organic cage (POC). Calculations identified that solvent molecules were the most stable when placed either inside the CC13 POC or in the pore window compared to interfacial binding sites. Structural changes to the CC13 POC correlated with reported experimental solubilities, including expansion of the CC13 POC with solvent molecule infiltration and expansion or contraction of the pore window. Based on these results, new PL design guidelines should include compositions with (1) high concentrations of POCs with flexible cage structures that can expand when solvated and (2) solvent molecule-POC combinations that contract the pore window during solvent molecule-host binding.

View Accepted Manuscript (DOE)

Research Organization:: Sandia National Laboratories (SNL-NM), Albuquerque, NM (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Laboratory Directed Research and Development (LDRD) Program; USDOE National Nuclear Security Administration (NNSA)

Grant/Contract Number:: NA0003525; SC0012577

OSTI ID:: 2311571

Alternate ID(s):: OSTI ID: 1959107

Report Number(s):: SAND--2023-01434J

Journal Information:: Journal of Molecular Liquids, Journal Name: Journal of Molecular Liquids Vol. 377; ISSN 0167-7322

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (42)

Modular Type III Porous Liquids Based on Porous Organic Cage Microparticles Kai, Aiting; Egleston, Benjamin D.; Tarzia, Andrew Advanced Functional Materials, Vol. 31, Issue 51 https://doi.org/10.1002/adfm.202106116	journal	September 2021
The Dam Bursts for Porous Liquids James, Stuart L. Advanced Materials, Vol. 28, Issue 27 https://doi.org/10.1002/adma.201505607	journal	March 2016
Porous Organic Cage Thin Films and Molecular-Sieving Membranes Song, Qilei; Jiang, Shan; Hasell, Tom Advanced Materials, Vol. 28, Issue 13 https://doi.org/10.1002/adma.201505688	journal	January 2016
Porous Ionic Liquids or Liquid Metal-Organic Frameworks? Costa Gomes, Margarida; Pison, Laure; Červinka, Ctirad Angewandte Chemie, Vol. 130, Issue 37 https://doi.org/10.1002/ange.201805495	journal	August 2018
Transforming Porous Organic Cages into Porous Ionic Liquids via a Supramolecular Complexation Strategy Jie, Kecheng; Onishi, Nicole; Schott, Jennifer A. Angewandte Chemie, Vol. 132, Issue 6 https://doi.org/10.1002/ange.201912068	journal	December 2019
Prediction of Reactive Nitrous Acid Formation in Rare‐Earth MOFs via ab initio Molecular Dynamics Vogel, Dayton J.; Rimsza, Jessica M.; Nenoff, Tina M. Angewandte Chemie, Vol. 133, Issue 20 https://doi.org/10.1002/ange.202102956	journal	April 2021
Controlling Gas Selectivity in Molecular Porous Liquids by Tuning the Cage Window Size Egleston, Benjamin D.; Luzyanin, Konstantin V.; Brand, Michael C. Angewandte Chemie International Edition, Vol. 59, Issue 19 https://doi.org/10.1002/anie.201914037	journal	March 2020
Porous Liquids O'Reilly, Niamh; Giri, Nicola; James, Stuart L. Chemistry - A European Journal, Vol. 13, Issue 11 https://doi.org/10.1002/chem.200700090	journal	April 2007
Porous Organic Compounds – Small Pores on the Rise Kunde, Tom; Pausch, Tobias; Schmidt, Bernd M. European Journal of Organic Chemistry, Vol. 2021, Issue 43 https://doi.org/10.1002/ejoc.202100892	journal	October 2021
Research Progress of Porous Liquids Li, Ying ChemistrySelect, Vol. 5, Issue 43 https://doi.org/10.1002/slct.202003957	journal	November 2020
Porous liquids based on porous cages, metal organic frameworks and metal organic polyhedra Bavykina, Anastasiya; Cadiau, Amandine; Gascon, Jorge Coordination Chemistry Reviews, Vol. 386 https://doi.org/10.1016/j.ccr.2019.01.015	journal	May 2019
Porous Liquids: The Next Frontier Fulvio, Pasquale Fernando; Dai, Sheng Chem, Vol. 6, Issue 12 https://doi.org/10.1016/j.chempr.2020.11.005	journal	December 2020
The interaction nature between hollow silica-based porous ionic liquids and CO2: A DFT study Zhang, Jinrui; Lv, Naixia; Chao, Yanhong Journal of Molecular Graphics and Modelling, Vol. 100 https://doi.org/10.1016/j.jmgm.2020.107694	journal	November 2020
Theoretical prediction of the SO2 absorption by hollow silica based porous ionic liquids Yin, Jie; Zhang, Jinrui; Fu, Wendi Journal of Molecular Graphics and Modelling, Vol. 103 https://doi.org/10.1016/j.jmgm.2020.107788	journal	March 2021
Theoretical insights into CO2/N2 selectivity of the porous ionic liquids constructed by ion-dipole interactions Yin, Jie; Zhang, Jinrui; Wang, Chao Journal of Molecular Liquids, Vol. 344 https://doi.org/10.1016/j.molliq.2021.117676	journal	December 2021
Synthesis of a Large, Shape-Flexible, Solvatomorphic Porous Organic Cage Teng, Baiyang; Little, Marc A.; Hasell, Tom Crystal Growth & Design, Vol. 19, Issue 7 https://doi.org/10.1021/acs.cgd.8b01761	journal	May 2019
Predictive Acid Gas Adsorption in Rare Earth DOBDC Metal–Organic Frameworks via Complementary Cluster and Periodic Structure Models Vogel, Dayton J.; Lee, Zachary R.; Hanson, Caitlin A. The Journal of Physical Chemistry C, Vol. 124, Issue 49 https://doi.org/10.1021/acs.jpcc.0c08282	journal	November 2020
Computational Evaluation of the Diffusion Mechanisms for C8 Aromatics in Porous Organic Cages Jackson, Edward; Miklitz, Marcin; Song, Qilei The Journal of Physical Chemistry C, Vol. 123, Issue 34 https://doi.org/10.1021/acs.jpcc.9b05953	journal	July 2019
Type 3 Porous Liquids for the Separation of Ethane and Ethene Lai, Beibei; Cahir, John; Tsang, Min Ying ACS Applied Materials & Interfaces, Vol. 13, Issue 1 https://doi.org/10.1021/acsami.0c19044	journal	December 2020
Porous Liquids: Computational Design for Targeted Gas Adsorption Rimsza, Jessica M.; Nenoff, Tina M. ACS Applied Materials & Interfaces, Vol. 14, Issue 16 https://doi.org/10.1021/acsami.2c03108	journal	April 2022
NO _x Adsorption and Optical Detection in Rare Earth Metal–Organic Frameworks Sava Gallis, Dorina F.; Vogel, Dayton J.; Vincent, Grace A. ACS Applied Materials & Interfaces, Vol. 11, Issue 46 https://doi.org/10.1021/acsami.9b16470	journal	October 2019
Tuned Hydrogen Bonding in Rare-Earth Metal–Organic Frameworks for Design of Optical and Electronic Properties: An Exemplar Study of Y–2,5-Dihydroxyterephthalic Acid Vogel, Dayton J.; Nenoff, Tina M.; Rimsza, Jessica M. ACS Applied Materials & Interfaces, Vol. 12, Issue 4 https://doi.org/10.1021/acsami.9b20513	journal	January 2020
Transforming Porous Silica Nanoparticles into Porous Liquids with Different Canopy Structures for CO₂ Capture Sheng, Lisha; Chen, Zhenqian; Wang, Xin ACS Omega, Vol. 7, Issue 7 https://doi.org/10.1021/acsomega.1c05091	journal	February 2022
Design Elements for Enhanced Hydrogen Isotope Separations in Barely Porous Organic Cages Vogel, Dayton J.; Nenoff, Tina M.; Rimsza, Jessica M. ACS Omega, Vol. 7, Issue 9 https://doi.org/10.1021/acsomega.1c07041	journal	February 2022
Accelerating Solvent Selection for Type II Porous Liquids Chang, Chao-Wen; Borne, Isaiah; Lawler, Robin M. Journal of the American Chemical Society, Vol. 144, Issue 9 https://doi.org/10.1021/jacs.1c13049	journal	February 2022
General Way To Construct Micro- and Mesoporous Metal–Organic Framework-Based Porous Liquids He, Sanfeng; Chen, Lihan; Cui, Jing Journal of the American Chemical Society, Vol. 141, Issue 50 https://doi.org/10.1021/jacs.9b08458	journal	November 2019
Molecular shape sorting using molecular organic cages Mitra, Tamoghna; Jelfs, Kim E.; Schmidtmann, Marc Nature Chemistry, Vol. 5, Issue 4 https://doi.org/10.1038/nchem.1550	journal	January 2013
Porous organic molecular solids by dynamic covalent scrambling Jiang, Shan; Jones, James T. A.; Hasell, Tom Nature Communications, Vol. 2, Issue 1 https://doi.org/10.1038/ncomms1207	journal	February 2011
Separation of rare gases and chiral molecules by selective binding in porous organic cages Chen, Linjiang; Reiss, Paul S.; Chong, Samantha Y. Nature Materials, Vol. 13, Issue 10 https://doi.org/10.1038/nmat4035	journal	July 2014
Understanding solvent effects on adsorption and protonation in porous catalysts Gould, Nicholas S.; Li, Sha; Cho, Hong Je Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-020-14860-6	journal	February 2020
Coordination cages as permanently porous ionic liquids Ma, Lillian; Haynes, Cally J. E.; Grommet, Angela B. Nature Chemistry, Vol. 12, Issue 3 https://doi.org/10.1038/s41557-020-0419-2	journal	February 2020
Solution processable metal–organic frameworks for mixed matrix membranes using porous liquids Knebel, Alexander; Bavykina, Anastasiya; Datta, Shuvo Jit Nature Materials, Vol. 19, Issue 12 https://doi.org/10.1038/s41563-020-0764-y	journal	August 2020
Chemical control of structure and guest uptake by a conformationally mobile porous material Katsoulidis, Alexandros P.; Antypov, Dmytro; Whitehead, George F. S. Nature, Vol. 565, Issue 7738 https://doi.org/10.1038/s41586-018-0820-9	journal	January 2019
Structure and electronic properties of rare earth DOBDC metal–organic-frameworks Vogel, Dayton J.; Sava Gallis, Dorina F.; Nenoff, Tina M. Physical Chemistry Chemical Physics, Vol. 21, Issue 41 https://doi.org/10.1039/C9CP04038B	journal	January 2019
Accelerated robotic discovery of type II porous liquids Kearsey, Rachel J.; Alston, Ben M.; Briggs, Michael E. Chemical Science, Vol. 10, Issue 41 https://doi.org/10.1039/C9SC03316E	journal	January 2019
Unraveling the mechanism of CO ₂ capture and separation by porous liquids Yin, Jie; Fu, Wendi; Zhang, Jinrui RSC Advances, Vol. 10, Issue 70 https://doi.org/10.1039/D0RA08039J	journal	January 2020
Introduction to Materials Studio Meunier, M. EPJ Web of Conferences, Vol. 30 https://doi.org/10.1051/epjconf/20123004001	journal	January 2012
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
Ab initiomolecular dynamics for liquid metals Kresse, G.; Hafner, J. Physical Review B, Vol. 47, Issue 1, p. 558-561 https://doi.org/10.1103/PhysRevB.47.558	journal	January 1993
Ab initio molecular-dynamics simulation of the liquid-metal–amorphous-semiconductor transition in germanium Kresse, G.; Hafner, J. Physical Review B, Vol. 49, Issue 20, p. 14251-14269 https://doi.org/10.1103/PhysRevB.49.14251	journal	May 1994
Restoring the Density-Gradient Expansion for Exchange in Solids and Surfaces Perdew, John P.; Ruzsinszky, Adrienn; Csonka, Gábor I. Physical Review Letters, Vol. 100, Issue 13 https://doi.org/10.1103/PhysRevLett.100.136406	journal	April 2008
Synthesis and Applications of Porous Organic Cages Evans, Jack D.; Sumby, Christopher J.; Doonan, Christian J. Chemistry Letters, Vol. 44, Issue 5 https://doi.org/10.1246/cl.150021	journal	May 2015

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