Covalent Organic Frameworks in 2013
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1 2014 Super Literature Lab, IMS Covalent Organic Frameworks in 2013 Presented by Dr. Shangbin Jin Feb. 7,
2 Covalent Organic Frameworks Covalent-bond linked (B-O, C=N,...) Light-weight element (C, B, O, N,...) Crystalline (XRD) Nanoporous (Gas sorption) 2 Jiang, et al, Chem. Soc. Rev. 2012, 41,
3 Why COFs? High Permanent Surface Area (3D COFs> 2D COFs) Low Density (< MOFs) Thermal Stability and Chemical Stability (> MOFs) Columnar π-stacking structure (2D COFs) Jiang, et al, Chem. Soc. Rev. 2012, 41,
4 Synthetic Methods for COFs Solvothermal Ionothermal COFs Synthetic Methods Microwave Surface Directed 4 Jiang, et al, Chem. Soc. Rev. 2012, 41,
5 Dynamic Covalent Chemistry Building Blocks Error correction Proof reading Oligomers Error correction Proof reading Network Structure Error correction Proof reading Covalent Organic Framework Thermodynamic control 5 Jiang, et al, Chem. Soc. Rev. 2012, 41,
6 Chemically reversible No compete reaction Symmetrical Geometry Rigid building blocks 6 Jiang et al, Chem. Soc. Rev. 2012, 41,
7 Covalent Organic Frameworks in 2013 New synthetic method New structural COFs New functional COFs 7
8 New Synthetic Methods for COFs Mechanochemical synthesis Figure Schematic representation of the mechanochemical synthesis of COFs (From J. Am. Chem. Soc. 2013, 135, ) Banerjee et al. J. Am. Chem. Soc. 2013, 135,
9 New Synthetic Methods for COFs Features of Mechanochemical synthesis of COFs Solvent free Room temperature Chemical stable Banerjee et al. J. Am. Chem. Soc. 2013, 135,
10 New synthetic methods for COFs Covalent Organic Nanosheets by Mechanochemical Route TpPa COF TpBa COFs Banerjee et al. J. Am. Chem. Soc. 2013, 135,
11 Graphene-like layer structures Figure Schematic Representation of synthesis of covalent organic nanosheets (From JACS 2013, 135, ) Banerjee et al. J. Am. Chem. Soc. 2013, 135,
12 On surface single-layered 2D COFs on HOPG Wan et al. J. Am. Chem. Soc. 2013, 135,
13 SCOF-IC1 on HOPG (Image from JACS 2013, ) Solid-vapor interface SCOF-LZU1on HOPG (Image from JACS 2013, ) Wan et al. J. Am. Chem. Soc. 2013, 135,
14 Thiophene-based 2D COFs T-COFs Sealed tube Dean- Stark Sealed tube+1% water Microwave N2 sealed bomb Air sealed bomb T-COF-1 T-COF-2 T-COF-1 + T- COF-2 T-COF-2 T-COF-1 + T- COF-2 NR T-COF-3 NR NR NR T-COF-3 T-COF-3 T-COF-4 T-COF-4 T-COF-4 T-COF-4 T-COF-4 T-COF-4 Dinca et al. PNAS
15 Thiophene-based 2D COFs p-type COF amenable to doping with acceptors Unprecedent intercalated charge transfer complex Dinca et al. PNAS
16 Mesoporous triptycene-derived COF Figure Experimental and Simulated PXRD of TDCOF-5 El-Kaderi, et al. CrystEngComm, 2013, 15,
17 BET SA: 2050 m 2 g -1 H2: 1.6 wt%, 77 K,1.0 bar CO2: 9.2 wt% (2.1 mmol g -1 ), 273 K, 1.0 bar CH4: 11.5 cm 3 g -1, 273 K, 1.0 bar El-Kaderi, et al. CrystEngComm, 2013, 15,
18 Synthesis of Cobalt Phthalocyanine COF CoPc-BPDA-COF Echegoyen, et al. CrystEngComm, 2013, 15,
19 Nitrogen sorption BET: 1087 m 2 g -1 Hydrogen sorption 1.2 wt%, 77K, 1 bar Methane sorption 0.59 wt% 273 K, 1 bar 0.45 wt% 298 K, 1 bar Echegoyen, et al. CrystEngComm, 2013, 15,
20 Phthalocyanine and Porphyrin COF CoPc-Por-COF BET: 1315 m 2 g -1 Echegoyen, et al. CrystEngComm, 2013, 15,
21 Phthalocyanine and Porphyrin COF Hydrogen: 0.8 wt% at 77 K, 1 bar Methane: 0.6 wt% at 298 K, 1 bar Echegoyen, et al. CrystEngComm, 2013, 15,
22 Lewis base mediated synthesis of COF-1 Fisher, et al. Chem. Commun., 2013, 49,
23 Synthesis of Covalent Organic Framework Nanofibers Liu et al, ACS Appl. Mater. Interfaces 2013, 5,
24 Synthesis of Covalent Organic Framework Nanofibers Liu et al, ACS Appl. Mater. Interfaces 2013, 5,
25 Synthesis of Covalent Organic Framework Nanofibers Figure SEM images of samples obtained from different reaction times: (a) 85 C for 2 h, (b) stop reaction when reach to 180 C, (c) 180 C for 5 h, and (d) 180 C for 24 h, and (e) their corresponding PXRD patterns. Liu et al, ACS Appl. Mater. Interfaces 2013, 5,
26 Humidity-Responsive Color-Changing Property R. H. 20% R. H. 60% R. H. 80% R. H. 100% Figure Photographs of the reversible humidity-responsive color changes of COF/aramid fabrics under different relative humidity Liu et al, ACS Appl. Mater. Interfaces 2013, 5,
27 A 2D Mesoporous Imine Covalent Organic Framework for High Pressure Gas Storage 2.3 nm ILCOF-1 El-Kaderi, et al. Chem. Eur. J. 2013, 19,
28 Nitrogen sorption curve and pore size distribution of ILCOF-1 BET: 2723 m 2 g -1 High Crystallinity PXRD pattern from El- Kaderi, et al. Chem. Eur. J. 2013, El-Kaderi, et al. Chem. Eur. J. 2013, 19,
29 Gas Storage H2: 1.3 wt.%, 77 K CH4: 0.9 wt.%, 273 K CO2: 6.0 wt.%, 273 K El-Kaderi, et al. Chem. Eur. J. 2013, 19,
30 Control of Crystallinity and Porosity of COF Self-complementary interaction Jiang et al, J. Am. Chem. Soc. 2013, 135,
31 Enhancement of Crystallinity of COFs Figure XRD patterns of the COFs. The insets show enlarged (001) facets. Jiang et al, J. Am. Chem. Soc. 2013, 135,
32 Control of Porosity in COFs Figure (A) Nitrogen sorption isotherm profiles measured at 77 K (red, CuP Ph COF; purple, CuP TFPh25; blue, CuP TFPh50; green, CuP TFPh75; black, CuP TFPh). (B) BET and (C) Langmuir surface areas. Jiang et al, J. Am. Chem. Soc. 2013, 135,
33 Enhancement of Chemical Stability and Crystallinity in Porphyrin COFs by Intramolecular Hydrogen Bonding DmaTph COF BET: 431 m 2 g -1 DhaTph COF BET: 1305 m 2 g -1 Banerjee, et al. Angew. Chem. Int. Ed. 2013, 52,
34 Enhancement of Crystallinity 3000 cps cps Banerjee, et al. Angew. Chem. Int. Ed. 2013, 52,
35 Enhancement of Chemical Stability Banerjee, et al. Angew. Chem. Int. Ed. 2013, 52,
36 Bulk Synthesis of Exfoliated 2D Hydrazone- Linked COFs Figure Exfoliation of COF-43 yields a suspension of few-layer 2D polymers Dichtel, et al. J. Am. Chem. Soc. 2013, 135,
37 Bulk Synthesis of Exfoliated 2D Hydrazone- Linked COFs Figure PXRD from different solvent (left) and the corresponding IR spectra (right). Dichtel, et al. J. Am. Chem. Soc. 2013, 135,
38 Bulk Synthesis of Exfoliated 2D Hydrazone-Linked COFs Figure Average size of COF-43 dispersions derived from DLS of solutions Figure AFM images of COF-43 in THF (a) and Dioxane (b) Dichtel, et al. J. Am. Chem. Soc. 2013, 135,
39 Post-Modification of 3D COF Mixed linkage Dichtel, et al. Chem. Commun., 2013, 49,
40 Post-Modification of 3D COF Thio-ene click chemistry Dichtel, et al. Chem. Commun., 2013, 49,
41 A Squaraine-linked Mesoporous COF New linkage Jiang et al, Angew. Chem. Int. Ed. 2013, 52,
42 A Squaraine-linked Mesoporous COF 2.1 nm Jiang et al, Angew. Chem. Int. Ed. 2013, 52,
43 A Squaraine-linked Mesoporous COF Zig-Zag Topology Jiang et al, Angew. Chem. Int. Ed. 2013, 52,
44 Heterogeneous Catalysts for Singlet Oxygene Generation Figure Absorption spectra of DPBF in the presence of CuP-SQ COF in DMF on irradiation at 500 nm. Arrows indicate the change of absorbance from 0 to 819 min upon irradiation with light. b) Plot of the DPBF content in the systems (black: CuP; red: CuP-SQ COF) versus the irradiation time. Jiang et al, Angew. Chem. Int. Ed. 2013, 52,
45 Charge Dynamics in A D-A COF D ZnPc -A NDI -COF Jiang, et al. Angew. Chem. Int. Ed. 2013, 52,
46 Charge Dynamics in A D-A COF PhCN DMF DMF DMF Figure Time-resolved transient absorption spectra in different solvetns Jiang, et al. Angew. Chem. Int. Ed. 2013, 52,
47 Charge Dynamics in A D-A COF Figure Time-resolved Electron Spin Resonance Spectrum in the solid state Jiang, et al. Angew. Chem. Int. Ed. 2013, 52,
48 Large Pore Donor-Acceptor COFs Jiang et al. Chem. Sci., 2013,4,
49 Azine-linked COF as Chemical Sensor Jiang et al, J. Am. Chem. Soc. 2013, 135,
50 High Chemical Stability of Azine-linked COF Jiang et al, J. Am. Chem. Soc. 2013, 135,
51 Azine-linked COF Chemical Sensor Selectively towards TNP: Hydrogen bonding formation Jiang et al, J. Am. Chem. Soc. 2013, 135,
52 Photoconductive Thiophene COF and Charge Transfer with Fullerene Bein, et al. Angew. Chem. Int. Ed. 2013, 52,
53 Figure Schematic representation of the host guest complex of TTCOF and a PCBM molecule to scale (From Bein et al, ACIE 2013) Solar cell PCE = 0.053% Bein, et al. Angew. Chem. Int. Ed. 2013, 52,
54 Conjugated Organic Framework with 3D Ordered Stable Structure and Delocalized π Clouds CS-COF Jiang et al. Nature Communications 2013, 4,2736 doi: /ncomms
55 Conjugated Organic Framework with 3D Ordered Stable Structure and Delocalized π Clouds PCE = 0.9% Jiang et al. Nature Communications 2013, 4,2736 doi: /ncomms
56 Single-Crystal Structure of COF Langmuir surface area of 2400 m 2 /g Methane15.0 wt % (176 cm 3 /cm 3 ) at 25 C and 80 bar. Yaghi, et al. J. Am. Chem. Soc. 2013, 135,
57 3D Rotation Electron Diffraction (RED) Method Single-crystal structure of COF-320 determined from RED data at 89 K. Figure (a) Representative adamantane-like cage in the diamond net. (b) Structure of COF-320 viewed along the a-axis shows a 9- fold interpenetration of a diamond net. (c) The 1D rectangle-shaped channels along the c-axis. Yaghi, et al. J. Am. Chem. Soc. 2013, 135,
58 Single-Crystal Structure of COF Figure (a) SEM image of the aggregation of crystallites. (b) The 3D reciprocal lattice of COF-320 reconstructed from the RED data collected from a crystal of 1.0 Å~ 0.5 Å~ 0.2 μm3 (insert). (c) (h0l) and (d) (hk0) slices cut from the reconstructed reciprocal lattice. (From Yaghi, et al. JACS 2013) Yaghi, et al. J. Am. Chem. Soc. 2013, 135,
59 Monocrystalline Covalent Organic Networks by Polymerization Figure Photographs of large single crystals of NPN-1, NPN-2 and NPN-3. a, Crystals of NPN-1 grown from 3:2 (vol/vol) mesitylene/ ethanol. b, Crystals of NPN-1 grown from 3:2 (vol/vol) benzene/ethanol. c, Crystals of NPN-2 grown from 3:2 (vol/vol) mesitylene/ methanol. d, Crystals of NPN-3 grown from 4:4:1 (vol/vol) mesitylene/ethanol/ tetrahydrofuran Wuest et al. Nature Chemistry 5, (2013) 59
60 Monocrystalline Covalent Organic Networks by Polymerization Figure Representations of the structures of crystals of covalent organic networks NPN-1, NPN-2 and NPN-3. a, NPN-1. b,c, Analogous representations of NPN-2 (b) and NPN-3 (c). Wuest et al. Nature Chemistry 5, (2013) 60
61 Reference list Banerjee, et al. J. Am. Chem. Soc. 2013, 135, Banerjee, et al. J. Am. Chem. Soc. 2013, 135, Wan, et al. J. Am. Chem. Soc. 2013, 135, Dinca, et al. Proc. Natl. Am. Sci El-Kaderi, et al. CrystEngComm, 2013, 15, Echegoyen, et al. CrystEngComm, 2013, 15, Fisher, et al. Chem. Commun., 2013, 49, Liu, et al. ACS Appl. Mater. Interfaces 2013, 5, El-Kaderi, et al. Chem. Eur. J. 2013, 19, Jiang, et al. J. Am. Chem. Soc. 2013, 135, Banerjee, et al. Angew. Chem. Int. Ed. 2013, 52, Dichtel, et al. J. Am. Chem. Soc. 2013, 135, Dichtel, et al. Chem. Commun., 2013, 49, Jiang, et al. Angew. Chem. Int. Ed. 2013, 52, Jiang, et al. Angew. Chem. Int. Ed. 2013, 52, Jiang, et al. Chem. Sci., 2013,4, Jiang, et al. J. Am. Chem. Soc. 2013, 135, Bein, et al. Angew. Chem. Int. Ed. 2013, 52, Jiang, et al. Nature Communications 2013, 4,2736 Yaghi, et al. J. Am. Chem. Soc. 2013, 135, Wuest, et al. Nature Chemistry 2013, 5,
62 Summary and Perspectives New Synthetic Method (new linkages) New Structural COFs (new skeletons) New Functional COFs (new functions) Well-Defined Structure COFs (single crystal) 62
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