Layered microporous polymers by solvent knitting method

Novel layered microporous polymers with high surface area and gas storage were prepared by low-cost solvent knitting method. Two-dimensional (2D) nanomaterials, especially 2D organic nanomaterials with unprecedentedly diverse and controlled structure, have attracted decent scientific interest. Among the preparation strategies, the top-down approach is one of the considered low-cost and scalable strategies to obtain 2D organic nanomaterials. However, some factors of their layered counterparts limited the development and potential applications of 2D organic nanomaterials, such as type, stability, and strict synthetic conditions of layered counterparts. We report a class of layered solvent knitting hyper-cross-linked microporous polymers (SHCPs) prepared by improving Friedel-Crafts reaction and using dichloroalkane as an economical solvent, stable electrophilic reagent, and external cross-linker at low temperature, which could be used as layered counterparts to obtain previously unknown 2D SHCP nanosheets by method of ultrasonic-assisted solvent exfoliation. This efficient and low-cost strategy can produce previously unreported microporous organic polymers with layered structure and high surface area and gas storage capacity. The pore structure and surface area of these polymers can be controlled by tuning the chain length of the solvent, the molar ratio of AlCl3, and the size of monomers. Furthermore, we successfully obtain an unprecedentedly high–surface area HCP material (3002 m2 g−1), which shows decent gas storage capacity (4.82 mmol g−1 at 273 K and 1.00 bar for CO2; 12.40 mmol g−1 at 77.3 K and 1.13 bar for H2). This finding provides an opportunity for breaking the constraint of former knitting methods and opening up avenues for the design and synthesis of previously unknown layered HCP materials.

[1]  V. Thomas.  Concepts and Perspectives , 2019, The Moral Universe of Shakespeare’s Problem Plays.

[2]  N. McKeown,et al.  Inexpensive polyphenylene network polymers with enhanced microporosity , 2016 .

[3]  Z. Tian,et al.  Catalysis with Two‐dimensional Materials and Their Heterostructures , 2016 .

[4]  R. Banerjee,et al.  Self-Exfoliated Guanidinium-Based Ionic Covalent Organic Nanosheets (iCONs). , 2016, Journal of the American Chemical Society.

[5]  S. De Feyter,et al.  Two-Dimensional Nanoporous Networks Formed by Liquid-to-Solid Transfer of Hydrogen-Bonded Macrocycles Built from DNA Bases. , 2016, Angewandte Chemie.

[6]  Renato Zenobi,et al.  Synthesis of a Two-Dimensional Covalent Organic Monolayer through Dynamic Imine Chemistry at the Air/Water Interface. , 2016, Angewandte Chemie.

[7]  B. T. King,et al.  Two-dimensional polymers: concepts and perspectives. , 2016, Chemical communications.

[8]  Akhilesh K. Gaharwar,et al.  Two-Dimensional Nanomaterials for Biomedical Applications: Emerging Trends and Future Prospects , 2015 .

[9]  A. Gaharwar,et al.  Two‐Dimensional Nanomaterials for Biomedical Applications: Emerging Trends and Future Prospects , 2015, Advanced materials.

[10]  R. M. Marcé,et al.  Hypercrosslinked materials: preparation, characterisation and applications , 2015 .

[11]  Wenchuan Wang,et al.  Systematic Tuning and Multifunctionalization of Covalent Organic Polymers for Enhanced Carbon Capture. , 2015, Journal of the American Chemical Society.

[12]  R. Zuckermann,et al.  The Organic Flatland—Recent Advances in Synthetic 2D Organic Layers , 2015, Advanced materials.

[13]  Hua Zhang,et al.  Wet-chemical synthesis and applications of non-layer structured two-dimensional nanomaterials , 2015, Nature Communications.

[14]  S. Lau,et al.  Functionalized graphene and other two-dimensional materials for photovoltaic devices: device design and processing. , 2015, Chemical Society reviews.

[15]  J. P. Olivier,et al.  Physisorption of gases, with special reference to the evaluation of surface area and pore size distribution (IUPAC Technical Report) , 2015 .

[16]  S. Dai,et al.  Hypercrosslinked phenolic polymers with well-developed mesoporous frameworks. , 2015, Angewandte Chemie.

[17]  Daniel J Murray,et al.  Large area synthesis of a nanoporous two-dimensional polymer at the air/water interface. , 2015, Journal of the American Chemical Society.

[18]  Dongqing Wu,et al.  Two‐Dimensional Soft Nanomaterials: A Fascinating World of Materials , 2015, Advanced materials.

[19]  Daqiang Yuan,et al.  A facile synthesis of microporous organic polymers for efficient gas storage and separation , 2015 .

[20]  M. Hillmyer,et al.  Hierarchically porous polymers from hyper-cross-linked block polymer precursors. , 2015, Journal of the American Chemical Society.

[21]  Qiang Wang,et al.  Recent advances in solid sorbents for CO2 capture and new development trends , 2014 .

[22]  L. Wan,et al.  Graphene‐Like Single‐Layered Covalent Organic Frameworks: Synthesis Strategies and Application Prospects , 2014, Advanced materials.

[23]  M. Wörle,et al.  Gram-scale synthesis of two-dimensional polymer crystals and their structure analysis by X-ray diffraction. , 2014, Nature chemistry.

[24]  Jiaxing Jiang,et al.  High surface area hypercrosslinked microporous organic polymer networks based on tetraphenylethylene for CO2 capture , 2014 .

[25]  S. Dai,et al.  Polymeric molecular sieve membranes via in situ cross-linking of non-porous polymer membrane templates , 2014, Nature Communications.

[26]  Lizhi Zhang,et al.  Direct visualization of surface-assisted two-dimensional diyne polycyclotrimerization. , 2014, Journal of the American Chemical Society.

[27]  Carey J. Johnson,et al.  Synthesis of a Covalent Monolayer Sheet by Photochemical Anthracene Dimerization at the Air/Water Interface and its Mechanical Characterization by AFM Indentation , 2014, Advanced materials.

[28]  Y. Bando,et al.  Nano boron nitride flatland. , 2014, Chemical Society reviews.

[29]  A. Ciesielski,et al.  Graphene via sonication assisted liquid-phase exfoliation. , 2014, Chemical Society reviews.

[30]  A. Nagai,et al.  Conjugated Microporous Polymers: Design, Synthesis and Application , 2013 .

[31]  R. Banerjee,et al.  Chemically stable multilayered covalent organic nanosheets from covalent organic frameworks via mechanical delamination. , 2013, Journal of the American Chemical Society.

[32]  William R. Dichtel,et al.  Bulk synthesis of exfoliated two-dimensional polymers using hydrazone-linked covalent organic frameworks. , 2013, Journal of the American Chemical Society.

[33]  A. Nagai,et al.  Conjugated microporous polymers: design, synthesis and application. , 2013, Chemical Society reviews.

[34]  L. Wan,et al.  On-surface synthesis of single-layered two-dimensional covalent organic frameworks via solid-vapor interface reactions. , 2013, Journal of the American Chemical Society.

[35]  J. Coleman,et al.  Liquid Exfoliation of Layered Materials , 2013, Science.

[36]  Wei Wang,et al.  Covalent Organic Frameworks (COFs): From Design to Applications , 2013 .

[37]  Yali Luo,et al.  Recent development of hypercrosslinked microporous organic polymers. , 2013, Macromolecular rapid communications.

[38]  K. Müllen,et al.  π-Conjugated heterotriangulene macrocycles by solution and surface-supported synthesis toward honeycomb networks. , 2013, Journal of the American Chemical Society.

[39]  A. Cooper,et al.  Chemical functionalization strategies for carbon dioxide capture in microporous organic polymers , 2013 .

[40]  Wei Wang,et al.  Covalent organic frameworks (COFs): from design to applications. , 2013, Chemical Society reviews.

[41]  F. Zamora,et al.  Tuning delamination of layered covalent organic frameworks through structural design. , 2012, Chemical communications.

[42]  A. Cooper,et al.  Impact of water coadsorption for carbon dioxide capture in microporous polymer sorbents. , 2012, Journal of the American Chemical Society.

[43]  Hani M. El‐Kaderi,et al.  Synthesis and Characterization of Porous Benzimidazole-Linked Polymers and Their Performance in Small Gas Storage and Selective Uptake , 2012 .

[44]  B. T. King,et al.  A two-dimensional polymer prepared by organic synthesis. , 2012, Nature chemistry.

[45]  Bao-hang Han,et al.  Microporous polycarbazole with high specific surface area for gas storage and separation. , 2012, Journal of the American Chemical Society.

[46]  S. Hecht,et al.  Controlling on-surface polymerization by hierarchical and substrate-directed growth. , 2012, Nature chemistry.

[47]  L. Wan,et al.  Construction and repair of highly ordered 2D covalent networks by chemical equilibrium regulation. , 2012, Chemical communications.

[48]  J. Fierro,et al.  Delamination of layered covalent organic frameworks. , 2011, Small.

[49]  W. Wang,et al.  A New Strategy to Microporous Polymers: Knitting Rigid Aromatic Building Blocks by External Cross-Linker , 2011 .

[50]  Renzhi Ma,et al.  Nanosheets of Oxides and Hydroxides: Ultimate 2D Charge‐Bearing Functional Crystallites , 2010, Advances in Materials.

[51]  Miaofang Chi,et al.  Direct exfoliation of natural graphite into micrometre size few layers graphene sheets using ionic liquids. , 2010, Chemical communications.

[52]  S. Grimme,et al.  A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. , 2010, The Journal of chemical physics.

[53]  SUPARNA DUTTASINHA,et al.  Graphene: Status and Prospects , 2009, Science.

[54]  J. Sakamoto,et al.  Two-dimensional polymers: just a dream of synthetic chemists? , 2009, Angewandte Chemie.

[55]  A. Gourdon,et al.  On-surface covalent coupling in ultrahigh vacuum. , 2008, Angewandte Chemie.

[56]  B. Lu,et al.  Alkylation of benzene and dichloromethane to diphenylmethane with acidic ionic liquids , 2008 .

[57]  Joost VandeVondele,et al.  Gaussian basis sets for accurate calculations on molecular systems in gas and condensed phases. , 2007, The Journal of chemical physics.

[58]  P. Budd,et al.  Polymers of Intrinsic Microporosity (PIMs): Organic Materials for Membrane Separations, Heterogeneous Catalysis and Hydrogen Storage , 2006 .

[59]  P. Budd,et al.  Polymers of intrinsic microporosity (PIMs): organic materials for membrane separations, heterogeneous catalysis and hydrogen storage. , 2006, Chemical Society reviews.

[60]  Serguei Patchkovskii,et al.  An Efficient a Posteriori Treatment for Dispersion Interaction in Density-Functional-Based Tight Binding. , 2005, Journal of chemical theory and computation.

[61]  Matthias Krack,et al.  Pseudopotentials for H to Kr optimized for gradient-corrected exchange-correlation functionals , 2005 .

[62]  J. Seiber.  Status and Prospects , 2005 .

[63]  A. Singh,et al.  A novel catalytic method for the alkylation of benzene to diphenylmethane over H‐ZSM‐5 zeolite catalysts , 1999 .

[64]  Sándor Suhai,et al.  Self-consistent-charge density-functional tight-binding method for simulations of complex materials properties , 1998 .

[65]  S. Goedecker,et al.  Relativistic separable dual-space Gaussian pseudopotentials from H to Rn , 1998, cond-mat/9803286.

[66]  K. Burke,et al.  Generalized Gradient Approximation Made Simple [Phys. Rev. Lett. 77, 3865 (1996)] , 1997 .

[67]  Burke,et al.  Generalized Gradient Approximation Made Simple. , 1996, Physical review letters.

[68]  K. Sing.  Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity (Recommendations 1984) , 1985 .

[69]  K. Sing,et al.  Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity (Provisional) , 1982 .

[70]  D. Nightingale.  Alkylation and the Action of Aluminum Halides on Alkylbenzenes. , 1939 .

[71]  Xiaodong Zhuang,et al.  Two‐Dimensional Soft Nanomaterials: A Fascinating World of Materials , 2015, Advanced materials.