A Porous Polyaromatic Solid for Vapor Adsorption of Xylene with High Efficiency, Selectivity, and Reusability

Overview

Journal Chemistry

Specialty Chemistry

Date 2022 Sep 21

PMID 36129172

Authors

Ryuki Sumida

Takeshi Matsumoto

Toshiyuki Yokoi

Michito Yoshizawa

Affiliations

Soon will be listed here.

Abstract

Development of porous materials capable of capturing volatile organic compounds (VOCs), such as benzene and its derivatives, with high efficiency, selectivity, and reusability is highly demanded. Here we report unusual vapor adsorption behavior toward VOCs by a new porous solid, composed of a polyaromatic capsule bearing a spherical nanocavity with subnano-sized windows. Without prior crystallization and high-temperature vacuum drying, the porous polyaromatic solid exhibits the following five features: vapor adsorption of benzene over cyclohexane with 90 % selectivity, high affinity toward o-xylene over benzene and toluene with >80 % selectivity, ortho-selective adsorption ability (>50 %) from mixed xylene isomers, tight VOCs storage even under high temperature and vacuum conditions, and at least 5 times reusability for xylene adsorption. The observed adsorption abilities are accomplished at ambient temperature and pressure within 1 h, which has not been demonstrated by organic/inorganic porous materials reported previously.

Citing Articles

Bioinspired Binding and Conversion of Linear Monoterpenes by Polyaromatic Coordination Capsules.

Sumida R, Catti L, Yoshizawa M ACS Org Inorg Au. 2024; 4(4):410-417.

PMID: 39132015 PMC: 11311458. DOI: 10.1021/acsorginorgau.4c00013.

A Review of the Preparation of Porous Fibers and Porous Parts by a Novel Micro-Extrusion Foaming Technique.

Wang Z, Huang H, Wang Y, Zhou M, Zhai W Materials (Basel). 2024; 17(1).

PMID: 38204024 PMC: 10779666. DOI: 10.3390/ma17010172.

A Closed Cavity Strategy for Selective Dipeptide Binding by a Polyaromatic Receptor in Water.

Shuto M, Sumida R, Yuasa M, Sawada T, Yoshizawa M JACS Au. 2023; 3(10):2905-2911.

PMID: 37885581 PMC: 10598568. DOI: 10.1021/jacsau.3c00484.

A Porous Polyaromatic Solid for Vapor Adsorption of Xylene with High Efficiency, Selectivity, and Reusability.

Sumida R, Matsumoto T, Yokoi T, Yoshizawa M Chemistry. 2022; 28(72):e202202825.

PMID: 36129172 PMC: 10092481. DOI: 10.1002/chem.202202825.

References

Sumida R, Matsumoto T, Yokoi T, Yoshizawa M . A Porous Polyaromatic Solid for Vapor Adsorption of Xylene with High Efficiency, Selectivity, and Reusability. Chemistry. 2022; 28(72):e202202825. PMC: 10092481. DOI: 10.1002/chem.202202825. View

Mastalerz M . Porous Shape-Persistent Organic Cage Compounds of Different Size, Geometry, and Function. Acc Chem Res. 2018; 51(10):2411-2422. DOI: 10.1021/acs.accounts.8b00298. View

du Plessis M, Nikolayenko V, Barbour L . Record-Setting Selectivity for -Xylene by an Intrinsically Porous Zero-Dimensional Metallocycle. J Am Chem Soc. 2020; 142(10):4529-4533. DOI: 10.1021/jacs.9b11314. View

Davis M . Ordered porous materials for emerging applications. Nature. 2002; 417(6891):813-21. DOI: 10.1038/nature00785. View

Kishida N, Tanaka Y, Yoshizawa M . CH-π Multi-Interaction-Driven Recognition and Isolation of Planar Compounds in a Spheroidal Polyaromatic Cavity. Chemistry. 2022; 28(69):e202202075. PMC: 10092702. DOI: 10.1002/chem.202202075. View

Kishi N, Li Z, Yoza K, Akita M, Yoshizawa M . An M2L4 molecular capsule with an anthracene shell: encapsulation of large guests up to 1 nm. J Am Chem Soc. 2011; 133(30):11438-41. DOI: 10.1021/ja2037029. View

Yamashina M, Matsuno S, Sei Y, Akita M, Yoshizawa M . Recognition of Multiple Methyl Groups on Aromatic Rings by a Polyaromatic Cavity. Chemistry. 2016; 22(40):14147-50. DOI: 10.1002/chem.201603032. View

Kitagawa S, Kitaura R, Noro S . Functional porous coordination polymers. Angew Chem Int Ed Engl. 2004; 43(18):2334-75. DOI: 10.1002/anie.200300610. View

Li J, Kuppler R, Zhou H . Selective gas adsorption and separation in metal-organic frameworks. Chem Soc Rev. 2009; 38(5):1477-504. DOI: 10.1039/b802426j. View

10.

Jie K, Liu M, Zhou Y, Little M, Pulido A, Chong S . Near-Ideal Xylene Selectivity in Adaptive Molecular Pillar[ n]arene Crystals. J Am Chem Soc. 2018; 140(22):6921-6930. PMC: 5997404. DOI: 10.1021/jacs.8b02621. View

11.

Niki K, Tsutsui T, Yamashina M, Akita M, Yoshizawa M . Recognition and Stabilization of Unsaturated Fatty Acids by a Polyaromatic Receptor. Angew Chem Int Ed Engl. 2020; 59(26):10489-10492. DOI: 10.1002/anie.202003253. View

12.

Yamashina M, Tsutsui T, Sei Y, Akita M, Yoshizawa M . A polyaromatic receptor with high androgen affinity. Sci Adv. 2019; 5(4):eaav3179. PMC: 6474769. DOI: 10.1126/sciadv.aav3179. View

13.

Kishi N, Li Z, Sei Y, Akita M, Yoza K, Siegel J . Wide-ranging host capability of a Pd(II)-linked M2L4 molecular capsule with an anthracene shell. Chemistry. 2013; 19(20):6313-20. DOI: 10.1002/chem.201204010. View

14.

Sumida R, Tanaka Y, Niki K, Sei Y, Toyota S, Yoshizawa M . Cyclic monoterpenes trapped in a polyaromatic capsule: unusual selectivity, isomerization, and volatility suppression. Chem Sci. 2021; 12(29):9946-9951. PMC: 8317663. DOI: 10.1039/d1sc01987b. View

15.

Cundy C, Cox P . The hydrothermal synthesis of zeolites: history and development from the earliest days to the present time. Chem Rev. 2003; 103(3):663-702. DOI: 10.1021/cr020060i. View

16.

Diercks C, Yaghi O . The atom, the molecule, and the covalent organic framework. Science. 2017; 355(6328). DOI: 10.1126/science.aal1585. View

17.

Moosa B, Alimi L, Shkurenko A, Fakim A, Bhatt P, Zhang G . A Polymorphic Azobenzene Cage for Energy-Efficient and Highly Selective p-Xylene Separation. Angew Chem Int Ed Engl. 2020; 59(48):21367-21371. DOI: 10.1002/anie.202007782. View

18.

Dobashi H, Catti L, Tanaka Y, Akita M, Yoshizawa M . N-Doping of Polyaromatic Capsules: Small Cavity Modification Leads to Large Change in Host-Guest Interactions. Angew Chem Int Ed Engl. 2020; 59(29):11881-11885. DOI: 10.1002/anie.202004168. View

19.

Sapianik A, Kovalenko K, Samsonenko D, Barsukova M, Dybtsev D, Fedin V . Exceptionally effective benzene/cyclohexane separation using a nitro-decorated metal-organic framework. Chem Commun (Camb). 2020; 56(59):8241-8244. DOI: 10.1039/d0cc03227a. View

20.

Acharyya K, Mukherjee P . Organic Imine Cages: Molecular Marriage and Applications. Angew Chem Int Ed Engl. 2019; 58(26):8640-8653. DOI: 10.1002/anie.201900163. View