Journal of the American Chemical Society
Page 6 of 14
Substituents on the Properties of Azine Linked Covalent Organic
Frameworks," CrystEngComm 2017.
demonstrated the value of VT-IR as
a tool to
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experimentally observe the existence of hydrogen
bonding between layers in a COF. From a practical
perspective, amide hydrogen bonding is important for
mechanical strength in polymeric materials, therefore,
reliable and designable methods to incorporate these
interactions in COFs could help expand them into new
applications. We also see this design strategy as a
general method that will allow for the synthesis of new
COF materials. Furthermore, this will enable monomers
that are too sterically bulky to interface with one another
to be effectively incorporated into 2D-COFs by
independently stabilizing the eclipsed stacking mode.
(7)
Chen, X.; Addicoat, M.; Irle, S.; Nagai, A.; Jiang, D.
"Control of Crystallinity and Porosity of Covalent Organic
Frameworks by Managing Interlayer Interactions Based on Self-
Complementary π-Electronic Force," J. Am. Chem. Soc. 2013, 135,
546-549.
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Salonen, L. M.; Medina, D. D.; Carbó-Argibay, E.;
Goesten, M. G.; Mafra, L.; Guldris, N.; Rotter, J. M.; Stroppa, D. G.;
Rodríguez-Abreu, C. "A Supramolecular Strategy Based on
Molecular Dipole Moments for High-Quality Covalent Organic
Frameworks," Chem. Commun. 2016, 52, 7986-7989.
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Vyas, V. S.; Haase, F.; Stegbauer, L.; Savasci, G.;
Podjaski, F.; Ochsenfeld, C.; Lotsch, B. V. "A Tunable Azine
Covalent Organic Framework Platform for Visible Light-Induced
Hydrogen Generation," Nat. Commun. 2015, 6, 8508.
ASSOCIATED CONTENT
Supporting Information
(10)
Thompson, C. M.; Occhialini, G.; McCandless, G. T.;
Alahakoon, S. B.; Cameron, V.; Nielsen, S. O.; Smaldone, R. A.
"Computational and Experimental Studies on the Effects of
Monomer Planarity on Covalent Organic Framework
Formation," J. Am. Chem. Soc. 2017, 139, 10506-10513.
Additional information and experimental results, including
solvent stability tests, solid-state NMR spectra, and
additional synthesis information are included in the
Supporting Information. The Supporting Information is
available free of charge on the ACS Publications website.
(11)
Halder, A.; Karak, S.; Addicoat, M.; Bera, S.;
Chakraborty, A.; Kunjattu, S. H.; Pachfule, P.; Heine, T.; Banerjee,
R. "Ultrastable Imine-Based Covalent Organic Frameworks for
Sulfuric Acid Recovery: An Effect of Interlayer Hydrogen
Bonding," Angew. Chem. Int. Ed. 2018, 57, 5797-5802.
AUTHOR INFORMATION
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Zhao, C.; Diercks, C. S.; Zhu, C.; Hanikel, N.; Pei, X.;
Corresponding Author
Yaghi, O. M. "Urea-Linked Covalent Organic Frameworks," J. Am.
Chem. Soc. 2018, 140, 16438-16441.
* Ronald A. Smaldone (ronald.smaldone@utdallas.edu)
(13)
Halder, A.; Ghosh, M.; Khayum M, A.; Bera, S.; Addicoat,
Author Contributions
M.; Sasmal, H. S.; Karak, S.; Kurungot, S.; Banerjee, R. "Interlayer
Hydrogen-Bonded Covalent Organic Frameworks as High-
Performance Supercapacitors," J. Am. Chem. Soc. 2018, 140,
10941-10945.
The manuscript was written through contributions of all
authors. All authors have given approval to the final version
of the manuscript.
(14)
Li, L.; Lu, F.; Xue, R.; Ma, B.; Li, Q.; Wu, N.; Liu, H.; Yao,
W.; Guo, H.; Yang, W. "Ultrastable Triazine-Based Covalent
Organic Framework with an Interlayer Hydrogen Bonding for
Supercapacitor Applications," ACS Appl. Mater. Interfaces 2019,
11, 26355-26363.
ACKNOWLEDGMENT
R.A.S acknowledges support from the Army Research
Laboratory (W911NF-18-2-0035).
The vibrational
spectroscopy and DFT simulations were supported by the
U.S. Department of Energy, Basic Energy Sciences, Division
of Materials Sciences and Engineering, Grant No. DE-
SC0019902 (K.T., T.T.). A.D.S acknowledges Consejo
Nacional de Ciencia y Tecnología (National Council for
Science and Technology) of Mexico for a doctoral fellowship.
We would also like to thank Prof. Mihaela Stefan, Dr. Hien
Nguyen and Dr. Ruwan Gunawardhana for their assistance
with solid-state NMR data collection.
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Kandambeth, S.; Shinde, D. B.; Panda, M. K.; Lukose, B.;
Heine, T.; Banerjee, R. "Enhancement of Chemical Stability and
Crystallinity in Porphyrin-Containing Covalent Organic
Frameworks by Intramolecular Hydrogen Bonds," Angew. Chem.
Int. Ed. 2013, 52, 13052-13056.
(16)
Mo, Y.-P.; Liu, X.-H.; Sun, B.; Yan, H.-J.; Wang, D.; Wan,
L.-J. "The Intramolecular H-Bonding Effect on the Growth and
Stability of Schiff-Base Surface Covalent Organic Frameworks,"
Phys. Chem. Chem. Phys. 2017, 19, 539-543.
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Kandambeth, S.; Venkatesh, V.; Shinde, D. B.; Kumari,
S.; Halder, A.; Verma, S.; Banerjee, R. "Self-Templated Chemically
Stable Hollow Spherical Covalent Organic Framework," Nat.
Commun. 2015, 6, 6786.
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