Moving Beyond Boron: The Emergence of New Linkage Chemistries in Covalent Organic Frameworks
Abstract
Since their discovery in 2005, covalent organic frameworks (COFs) have attracted interest as potential materials for gas storage, catalysis, energy storage, and other applications because of their ability to periodically and reliably organize designed functionality into high surface area materials. Most of the first examples relied on boron-containing linkages, which suffer from hydrolytic and oxidative instability that limit their utility. In this Perspective, we describe the trend toward more robust linkages by highlighting the design, synthesis, and properties of several recent examples. Finally, the continued development of new COF chemistries, along with improved understanding of their formation and control of their final form, will provide a means to harness their molecularly precise solidstate structures for useful purposes.
- Authors:
-
- Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, United States
- Publication Date:
- Research Org.:
- Energy Frontier Research Centers (EFRC) (United States). Energy Materials Center at Cornell (EMC2); Cornell Univ., Ithaca, NY (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); Camille and Henry Dreyfus Foundation (United States); US Army Research Office (ARO); National Science Foundation (NSF)
- OSTI Identifier:
- 1258501
- Alternate Identifier(s):
- OSTI ID: 1288690
- Grant/Contract Number:
- FG02-87ER45298; SC000001086; W911NF-15-1-0447; DGE-1144153
- Resource Type:
- Published Article
- Journal Name:
- Macromolecules
- Additional Journal Information:
- Journal Name: Macromolecules Journal Volume: 49 Journal Issue: 15; Journal ID: ISSN 0024-9297
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
DeBlase, Catherine R., and Dichtel, William R. Moving Beyond Boron: The Emergence of New Linkage Chemistries in Covalent Organic Frameworks. United States: N. p., 2016.
Web. doi:10.1021/acs.macromol.6b00891.
DeBlase, Catherine R., & Dichtel, William R. Moving Beyond Boron: The Emergence of New Linkage Chemistries in Covalent Organic Frameworks. United States. https://doi.org/10.1021/acs.macromol.6b00891
DeBlase, Catherine R., and Dichtel, William R. Tue .
"Moving Beyond Boron: The Emergence of New Linkage Chemistries in Covalent Organic Frameworks". United States. https://doi.org/10.1021/acs.macromol.6b00891.
@article{osti_1258501,
title = {Moving Beyond Boron: The Emergence of New Linkage Chemistries in Covalent Organic Frameworks},
author = {DeBlase, Catherine R. and Dichtel, William R.},
abstractNote = {Since their discovery in 2005, covalent organic frameworks (COFs) have attracted interest as potential materials for gas storage, catalysis, energy storage, and other applications because of their ability to periodically and reliably organize designed functionality into high surface area materials. Most of the first examples relied on boron-containing linkages, which suffer from hydrolytic and oxidative instability that limit their utility. In this Perspective, we describe the trend toward more robust linkages by highlighting the design, synthesis, and properties of several recent examples. Finally, the continued development of new COF chemistries, along with improved understanding of their formation and control of their final form, will provide a means to harness their molecularly precise solidstate structures for useful purposes.},
doi = {10.1021/acs.macromol.6b00891},
journal = {Macromolecules},
number = 15,
volume = 49,
place = {United States},
year = {Tue Jun 21 00:00:00 EDT 2016},
month = {Tue Jun 21 00:00:00 EDT 2016}
}
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1021/acs.macromol.6b00891
https://doi.org/10.1021/acs.macromol.6b00891
Other availability
Search WorldCat to find libraries that may hold this journal
Cited by: 90 works
Citation information provided by
Web of Science
Web of Science
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referencing / citing this record:
Stack the Bowls: Tailoring the Electronic Structure of Corannulene-Integrated Crystalline Materials
journal, July 2018
- Rice, Allison M.; Dolgopolova, Ekaterina A.; Yarbrough, Brandon J.
- Angewandte Chemie International Edition, Vol. 57, Issue 35
Rapid access to substituted 2-naphthyne intermediates via the benzannulation of halogenated silylalkynes
journal, January 2017
- Hein, Samuel J.; Lehnherr, Dan; Dichtel, William R.
- Chemical Science, Vol. 8, Issue 8
Advanced Porous Materials in Mixed Matrix Membranes
journal, July 2018
- Cheng, Youdong; Ying, Yunpan; Japip, Susilo
- Advanced Materials, Vol. 30, Issue 47
Processing of covalent organic frameworks: an ingredient for a material to succeed
journal, January 2019
- Rodríguez-San-Miguel, David; Zamora, Félix
- Chemical Society Reviews, Vol. 48, Issue 16
Advanced Porous Materials in Mixed Matrix Membranes
journal, July 2018
- Cheng, Youdong; Ying, Yunpan; Japip, Susilo
- Advanced Materials, Vol. 30, Issue 47
Stack the Bowls: Tailoring the Electronic Structure of Corannulene-Integrated Crystalline Materials
journal, July 2018
- Rice, Allison M.; Dolgopolova, Ekaterina A.; Yarbrough, Brandon J.
- Angewandte Chemie, Vol. 130, Issue 35
Rapid access to substituted 2-naphthyne intermediates via the benzannulation of halogenated silylalkynes
journal, January 2017
- Hein, Samuel J.; Lehnherr, Dan; Dichtel, William R.
- Chemical Science, Vol. 8, Issue 8
Processing of covalent organic frameworks: an ingredient for a material to succeed
journal, January 2019
- Rodríguez-San-Miguel, David; Zamora, Félix
- Chemical Society Reviews, Vol. 48, Issue 16
Exceptional Iodine Capture in 2D Covalent Organic Frameworks
journal, May 2018
- Wang, Ping; Xu, Qing; Li, Zhongping
- Advanced Materials, Vol. 30, Issue 29
Efficient removal of organic dye pollutants using covalent organic frameworks
journal, March 2017
- Zhu, Xiang; An, Shuhao; Liu, Yu
- AIChE Journal, Vol. 63, Issue 8
A Highly Stable Porous Viologen Polymer for the Catalysis of Debromination Coupling of Benzyl Bromides with High Recyclability
journal, August 2019
- Tang, Jia‐Kang; Yu, Shang‐Bo; Liu, Chuan‐Zhi
- Asian Journal of Organic Chemistry, Vol. 8, Issue 10
Heißes Wasser ermöglicht Kristallinität in organischen Materialien
journal, January 2018
- Unterlass, Miriam M.
- Angewandte Chemie, Vol. 130, Issue 9
Hot Water Generates Crystalline Organic Materials
journal, January 2018
- Unterlass, Miriam M.
- Angewandte Chemie International Edition, Vol. 57, Issue 9
Stack the Bowls: Tailoring the Electronic Structure of Corannulene-Integrated Crystalline Materials
journal, July 2018
- Rice, Allison M.; Dolgopolova, Ekaterina A.; Yarbrough, Brandon J.
- Angewandte Chemie International Edition, Vol. 57, Issue 35
2D Poly(arylene vinylene) Covalent Organic Frameworks via Aldol Condensation of Trimethyltriazine
journal, September 2019
- Jadhav, Thaksen; Fang, Yuan; Patterson, William
- Angewandte Chemie International Edition, Vol. 58, Issue 39
A Dual Threat: Redox‐Activity and Electronic Structures of Well‐Defined Donor–Acceptor Fulleretic Covalent‐Organic Materials
journal, February 2020
- Leith, Gabrielle A.; Rice, Allison M.; Yarbrough, Brandon J.
- Angewandte Chemie International Edition, Vol. 59, Issue 15
Highly Crystalline and Semiconducting Imine‐Based Two‐Dimensional Polymers Enabled by Interfacial Synthesis
journal, February 2020
- Sahabudeen, Hafeesudeen; Qi, Haoyuan; Ballabio, Marco
- Angewandte Chemie International Edition, Vol. 59, Issue 15
Equilibration of Imine-Linked Polymers to Hexagonal Macrocycles Driven by Self-Assembly
journal, February 2018
- Chavez, Anton D.; Evans, Austin M.; Flanders, Nathan C.
- Chemistry - A European Journal, Vol. 24, Issue 16
Tailoring Covalent Organic Frameworks To Capture Water Contaminants
journal, February 2019
- Fernandes, Soraia P. S.; Romero, Vanesa; Espiña, Begoña
- Chemistry – A European Journal, Vol. 25, Issue 26
Two-Dimensional Covalent Organic Frameworks for Optoelectronics and Energy Storage
journal, May 2017
- Mandal, Amal Kumar; Mahmood, Javeed; Baek, Jong-Beom
- ChemNanoMat, Vol. 3, Issue 6
Synthesis, characterization, and CO 2 uptake of mellitic triimide‐based covalent organic frameworks
journal, October 2019
- Veldhuizen, Hugo; Vasileiadis, Alexandros; Wagemaker, Marnix
- Journal of Polymer Science Part A: Polymer Chemistry, Vol. 57, Issue 24
Structural Elucidation of Covalent Organic Polymers (COP) and Their Linker Effect on Gas Adsorption Performance via Density Functional Theory Approach
journal, July 2018
- Aparicio, Santiago; Yavuz, Cafer T.; Atilhan, Mert
- ChemistrySelect, Vol. 3, Issue 28
A 2D covalent organic framework as a sensor for detecting formaldehyde
journal, June 2018
- Wang, Yaping; Zhao, Zhengyan; Li, Guanglan
- Journal of Molecular Modeling, Vol. 24, Issue 7
Approaches and challenges in the synthesis of three-dimensional covalent-organic frameworks
journal, December 2018
- Ma, Xingjian; Scott, Timothy F.
- Communications Chemistry, Vol. 1, Issue 1
Covalent organic frameworks (COFs): perspectives of industrialization
journal, January 2018
- Zhao, Wei; Xia, Lieyin; Liu, Xikui
- CrystEngComm, Vol. 20, Issue 12
Growth of high-quality covalent organic framework nanosheets at the interface of two miscible organic solvents
journal, January 2018
- Li, Yang; Zhang, Meicheng; Guo, Xinghua
- Nanoscale Horizons, Vol. 3, Issue 2
Dramatic improvement of stability by in situ linker cyclization of a metal–organic framework
journal, January 2018
- Hou, Yun-Long; Li, Mu-Qing; Cheng, Shengxian
- Chemical Communications, Vol. 54, Issue 68
Improved synthesis of β-ketoenamine-linked covalent organic frameworks via monomer exchange reactions
journal, January 2019
- Daugherty, Michael C.; Vitaku, Edon; Li, Rebecca L.
- Chemical Communications, Vol. 55, Issue 18
Recent progress in covalent organic framework thin films: fabrications, applications and perspectives
journal, January 2019
- Wang, Han; Zeng, Zhuotong; Xu, Piao
- Chemical Society Reviews, Vol. 48, Issue 2
Emerging porous materials in confined spaces: from chromatographic applications to flow chemistry
journal, January 2019
- Zhang, Jianyong; Chen, Junxing; Peng, Sheng
- Chemical Society Reviews, Vol. 48, Issue 9
Post-synthetic modification of covalent organic frameworks
journal, January 2019
- Segura, José L.; Royuela, Sergio; Mar Ramos, M.
- Chemical Society Reviews, Vol. 48, Issue 14
Two-dimensional nanosheet-based gas separation membranes
journal, January 2018
- Liu, Min; Gurr, Paul A.; Fu, Qiang
- Journal of Materials Chemistry A, Vol. 6, Issue 46
Covalent organic frameworks from a monomer with reduced symmetry: polymorphism and Sierpiński triangles
journal, January 2019
- Cui, Daling; Fang, Yuan; MacLean, Oliver
- Chemical Communications, Vol. 55, Issue 90
The luminescent and photophysical properties of covalent organic frameworks
journal, January 2020
- Haug, W. Karl; Moscarello, Erica M.; Wolfson, Eric R.
- Chemical Society Reviews, Vol. 49, Issue 3
Covalent Organic Frameworks: From Materials Design to Biomedical Application
journal, December 2017
- Zhao, Fuli; Liu, Huiming; Mathe, Salva
- Nanomaterials, Vol. 8, Issue 1