Rapid Synthesis of High Surface Area Imine‐Linked 2D Covalent Organic Frameworks by Avoiding Pore Collapse During Isolation

Feriante, Cameron H.; Jhulki, Samik; Evans, Austin M.; Dasari, Raghunath R.; Slicker, Kaitlin; Dichtel, William R.; Marder, Seth R.

doi:10.1002/adma.201905776

Title: Rapid Synthesis of High Surface Area Imine‐Linked 2D Covalent Organic Frameworks by Avoiding Pore Collapse During Isolation

Journal Article · 25 November 2019 · Advanced Materials

DOI: https://doi.org/10.1002/adma.201905776 · OSTI ID:1575781

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School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics Georgia Institute of Technology Atlanta GA 30332‐0400 USA
Department of Chemistry Northwestern University 2145 Sheridan Road Evanston IL 60208 USA

Abstract Imine‐linked 2D covalent organic frameworks (COFs) form more rapidly than previously reported under Brønsted acid‐catalyzed conditions, showing signs of crystallinity within a few minutes, and maximum crystallinity within hours. These observations contrast with the multiday reaction times typically employed under these conditions. In addition, vacuum activation, which is often used to isolate COF materials significantly erodes the crystallinity and surface area of the several isolated materials, as measured by N ₂ sorption and X‐ray diffraction. This loss of material quality during isolation for many networks has historically obscured otherwise effective polymerization conditions. The influence of the activation procedure is characterized in detail for three COFs, with the commonly used 1,3,5‐tris(4‐aminophenyl)benzene‐terephthaldehyde network (TAPB‐PDA COF), the most prone to pore collapse. When the networks are activated carefully, rapid COF formation is general for all five of the imine‐linked 2D COFs studied, with all exhibiting excellent crystallinity and surface areas, including the highest surface areas reported to date for three materials. Furthermore, to simplify the workup of COF materials, a simple nitrogen flow method provides high‐quality materials without the need for specialized equipment. These insights have important implications for studying and understanding how 2D COFs form.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1575781

Journal Information:: Advanced Materials, Journal Name: Advanced Materials Journal Issue: 2 Vol. 32; ISSN 0935-9648

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

References (27)

Covalent Organic Frameworks for CO ₂ Capture Zeng, Yongfei; Zou, Ruqiang; Zhao, Yanli Advanced Materials, Vol. 28, Issue 15 https://doi.org/10.1002/adma.201505004	journal	February 2016
A Photoconductive Covalent Organic Framework: Self-Condensed Arene Cubes Composed of Eclipsed 2D Polypyrene Sheets for Photocurrent Generation Wan, Shun; Guo, Jia; Kim, Jangbae Angewandte Chemie International Edition, Vol. 48, Issue 30 https://doi.org/10.1002/anie.200900881	journal	July 2009
A Photoconductive Thienothiophene-Based Covalent Organic Framework Showing Charge Transfer Towards Included Fullerene Dogru, Mirjam; Handloser, Matthias; Auras, Florian Angewandte Chemie International Edition, Vol. 52, Issue 10 https://doi.org/10.1002/anie.201208514	journal	February 2013
Rapid Guest Exchange and Ultra-Low Surface Tension Solvents Optimize Metal-Organic Framework Activation Ma, Jialiu; Kalenak, Andre P.; Wong-Foy, Antek G. Angewandte Chemie International Edition, Vol. 56, Issue 46 https://doi.org/10.1002/anie.201709187	journal	October 2017
Chemically Stable Covalent Organic Framework (COF)-Polybenzimidazole Hybrid Membranes: Enhanced Gas Separation through Pore Modulation Biswal, Bishnu P.; Chaudhari, Harshal D.; Banerjee, Rahul Chemistry - A European Journal, Vol. 22, Issue 14 https://doi.org/10.1002/chem.201504836	journal	February 2016
BODIPY-Decorated Nanoscale Covalent Organic Frameworks for Photodynamic Therapy Guan, Qun; Fu, Dan-Dan; Li, Yan-An iScience, Vol. 14 https://doi.org/10.1016/j.isci.2019.03.028	journal	April 2019
The Metal–Organic Framework Collapse Continuum: Insights from Two-Dimensional Powder X-ray Diffraction Dodson, Ryan A.; Wong-Foy, Antek G.; Matzger, Adam J. Chemistry of Materials, Vol. 30, Issue 18 https://doi.org/10.1021/acs.chemmater.8b03378	journal	September 2018
Functional Naphthalene Diimides: Synthesis, Properties, and Applications Al Kobaisi, Mohammad; Bhosale, Sidhanath V.; Latham, Kay Chemical Reviews, Vol. 116, Issue 19 https://doi.org/10.1021/acs.chemrev.6b00160	journal	August 2016
Buckling of Two-Dimensional Covalent Organic Frameworks under Thermal Stress Evans, Austin M.; Ryder, Matthew R.; Flanders, Nathan C. Industrial & Engineering Chemistry Research, Vol. 58, Issue 23 https://doi.org/10.1021/acs.iecr.9b01288	journal	May 2019
Imparting Catalytic Activity to a Covalent Organic Framework Material by Nanoparticle Encapsulation Shi, Xiaofei; Yao, Youjin; Xu, Yulong ACS Applied Materials & Interfaces, Vol. 9, Issue 8 https://doi.org/10.1021/acsami.6b16267	journal	February 2017
Naphthalene Diimide-Based Polymer Semiconductors: Synthesis, Structure–Property Correlations, and n-Channel and Ambipolar Field-Effect Transistors Guo, Xugang; Kim, Felix Sunjoo; Seger, Mark J. Chemistry of Materials, Vol. 24, Issue 8 https://doi.org/10.1021/cm2034273	journal	April 2012
Supercritical Processing as a Route to High Internal Surface Areas and Permanent Microporosity in Metal−Organic Framework Materials Nelson, Andrew P.; Farha, Omar K.; Mulfort, Karen L. Journal of the American Chemical Society, Vol. 131, Issue 2, p. 458-460 https://doi.org/10.1021/ja808853q	journal	January 2009
Chemical Conversion of Linkages in Covalent Organic Frameworks Waller, Peter J.; Lyle, Steven J.; Osborn Popp, Thomas M. Journal of the American Chemical Society, Vol. 138, Issue 48 https://doi.org/10.1021/jacs.6b08377	journal	November 2016
Synchronized Offset Stacking: A Concept for Growing Large-Domain and Highly Crystalline 2D Covalent Organic Frameworks Auras, Florian; Ascherl, Laura; Hakimioun, Amir H. Journal of the American Chemical Society, Vol. 138, Issue 51 https://doi.org/10.1021/jacs.6b09787	journal	December 2016
Rapid, Low Temperature Formation of Imine-Linked Covalent Organic Frameworks Catalyzed by Metal Triflates Matsumoto, Michio; Dasari, Raghunath R.; Ji, Woojung Journal of the American Chemical Society, Vol. 139, Issue 14 https://doi.org/10.1021/jacs.7b01240	journal	March 2017
Switching on and off Interlayer Correlations and Porosity in 2D Covalent Organic Frameworks Sick, Torben; Rotter, Julian M.; Reuter, Stephan Journal of the American Chemical Society, Vol. 141, Issue 32 https://doi.org/10.1021/jacs.9b02800	journal	June 2019
De Novo Design and Facile Synthesis of 2D Covalent Organic Frameworks: A Two-in-One Strategy Li, Yusen; Chen, Qing; Xu, Tiantian Journal of the American Chemical Society, Vol. 141, Issue 35 https://doi.org/10.1021/jacs.9b03463	journal	August 2019
Structure of the amorphous phase in crystallizable polymers: poly(ethylene terephthalate) Murthy, N. S.; Correale, S. T.; Minor, H. Macromolecules, Vol. 24, Issue 5 https://doi.org/10.1021/ma00005a033	journal	September 1991
Covalent organic frameworks: a materials platform for structural and functional designs Huang, Ning; Wang, Ping; Jiang, Donglin Nature Reviews Materials, Vol. 1, Issue 10 https://doi.org/10.1038/natrevmats.2016.68	journal	September 2016
Stable, crystalline, porous, covalent organic frameworks as a platform for chiral organocatalysts Xu, Hong; Gao, Jia; Jiang, Donglin Nature Chemistry, Vol. 7, Issue 11 https://doi.org/10.1038/nchem.2352	journal	September 2015
Bottom-up synthesis of chiral covalent organic frameworks and their bound capillaries for chiral separation Qian, Hai-Long; Yang, Cheng-Xiong; Yan, Xiu-Ping Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms12104	journal	July 2016
Facile transformation of imine covalent organic frameworks into ultrastable crystalline porous aromatic frameworks Li, Xinle; Zhang, Changlin; Cai, Songliang Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-05462-4	journal	July 2018
Solvatochromic covalent organic frameworks Ascherl, Laura; Evans, Emrys W.; Hennemann, Matthias Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-06161-w	journal	September 2018
Insight into the crystallization of amorphous imine-linked polymer networks to 2D covalent organic frameworks Smith, Brian J.; Overholts, Anna C.; Hwang, Nicky Chemical Communications, Vol. 52, Issue 18 https://doi.org/10.1039/C5CC10221A	journal	January 2016
Enhanced proton conduction by post-synthetic covalent modification in a porous covalent framework Samanta, Partha; Desai, Aamod V.; Anothumakkool, Bihag Journal of Materials Chemistry A, Vol. 5, Issue 26 https://doi.org/10.1039/C7TA00964J	journal	January 2017
Porous, Crystalline, Covalent Organic Frameworks Côté, Adrien P.; Benin, Annabelle I.; Ockwig, Nathan W. Science, Vol. 310, Issue 5751, p. 1166-1170 https://doi.org/10.1126/science.1120411	journal	November 2005
Increasing the Stability of Metal-Organic Frameworks Bosch, Mathieu; Zhang, Muwei; Zhou, Hong-Cai Advances in Chemistry, Vol. 2014 https://doi.org/10.1155/2014/182327	journal	September 2014

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