Structure of 118727-34-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
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Tong, Xinbo ; Ridenour, Brian D ; Saji Kumar, Abhishek ; Feng, Shuai ; Nettles, Jared ; Lin, Jerry YS , et al.
Abstract: Covalent organic framework (COF) aerogels are hierarchically porous polymeric materials with ultrahigh specific surface area, making them attractive for wide applications such as molecular capture, adsorption, and catalysis. Previous COF aerogel studies have focused on varying their chemical structures and linkage chemistries to fine-tune material properties and functionality, most of which have reported relatively unsatisfying performance (e.g., poor mechanical strength and strain tolerance). This study describes the synthesis and characterization of COF nanocomposite aerogels, whose material properties and functionality are effectively engineered through the incorporation of reinforcing fillers/binders or functional additives. Boron nitride (BN) fillers, cross-linked poly(acrylic acid) (XPAA) binders, and gold nanoparticles (AuNps) are incorporated into 1,3,5-tris(aminophenyl)benzene-terephthaldehyde (TAPB-PDA) COF aerogel matrices to form homogeneous nanocomposite aerogels with enhanced mechanical properties and unique photothermal conversion capabilities. Fourier transform infrared spectroscopy, X-ray diffraction, thermogravimetric analysis, and scanning electron microscopy results confirm the successful filler/additive inclusion into the final COF nanocomposite aerogels. Specifically, BN filler loading at ∼17 wt % relative to final COF mass doubles COF aerogel’s Young’s modulus from 11 to 22 kPa according to mechanical compression tests, with only ∼10% reduction in COF’s accessible mesopores’ surface area according to nitrogen porosimeter analyses. Meanwhile, incorporating ∼7 wt % XPAA relative to final COF mass improves the Young’s modulus to 21 kPa, while increasing the aerogel’s yield strain from 10 to 65% strain, although this leads to a ∼35% reduction in COF’s accessible mesopores’ surface area. Furthermore, photothermal AuNps are incorporated to form functional COF nanocomposite aerogels, whose overall temperature increases by 5.5 °C after 1 sun (AM1.5G, 1000 W m−2) irradiation. Overall, this study demonstrates potential routes to fabricate hierarchically porous COF nanocomposite aerogels with high specific surface area, robust mechanical stability, and unique photothermal functionality, which hold promises for applications in adsorption separation, gas storage, and photocatalysis.
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Keywords: covalent organic framework (COF) ; aerogel ; composites ; hierarchically porous ; high surface area ; mechanically strong ; photothermal ; adsorption
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Jeremy P. Daum ; Alec Ajnsztajn ; Sathvik Ajay Iyengar ; Jacob Lowenstein ; Soumyabrata Roy ; Guan-hui Gao , et al.
Abstract: Covalent organic frameworks (COFs) are a promising class of crystalline polymer networks that are useful due to their high porosity, versatile functionality, and tunable architecture. Conventional solution-based methods of producing COFs are marred by slow reactions that produce powders that are difficult to process into adaptable form factors for functional applications, and there is a need for facile and fast synthesis techniques for making crystalline and ordered covalent organic framework (COF) thin films. In this work, we report a chemical vapor deposition (CVD) approach utilizing co-evaporation of two monomers onto a heated substrate to produce highly crystalline, defect-free COF films and coatings with hydrazone, imine, and ketoenamine COF linkages. This all-in-one synthesis technique produces highly crystalline, 40 nm–1 μm-thick COF films on Si/SiO2 substrates in less than 30 min. Crystallinity and alignment were proven by using a combination of grazing-incidence wide-angle X-ray scattering (GIWAXS) and transmission electron microscopy (TEM), and successful conversion of the monomers to produce the target COF was supported by Raman spectroscopy, X-ray photoelectron spectroscopy (XPS), and UV–vis measurements. Additionally, we used atomic force microscopy (AFM) to investigate the growth mechanisms of these films, showing the coalescence of triangular crystallites into a smooth film. To show the wide applicability and scope of the CVD process, we also prepared crystalline ordered COF films with imine and ketoenamine linkages. These films show potential as high-quality size exclusion membranes, catalytic platforms, and organic transistors.
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Keywords: covalent organic frameworks ; chemical vapor deposition ; thin films ; cof-42 ; polymers ; monomers
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Khalil, Safiya ; Meyer, Matthew D ; Alazmi, Abdullah ; Samani, Mohammad HK ; Huang, Po-Chun ; Barnes, Morgan , et al.
Abstract: Covalent organic frameworks (COFs) are crystalline, nanoporous materials of interest for various applications, but current COF synthetic routes lead to insoluble aggregates which precludes processing for practical implementation. Here, we report a COF synthesis method that produces a stable, homogeneous suspension of crystalline COF nanoparticles that enables the preparation of COF monoliths, membranes, and films using conventional solution processing techniques. Our approach involves the use of a polar solvent, di-acid catalyst, and slow reagent mixing procedure at elevated temperatures which altogether enable access to crystalline COF nanoparticle suspension that does not aggregate or precipitate when kept at elevated temperatures. On cooling, the suspension undergoes a thermoreversible gelation transition to produce crystalline and highly porous COF materials. We further show that the modified synthesis approach is compatible with various COF chemistries, including both large- and small-pore imine COFs, hydrazone-linked COFs, and COFs with rhombic and hexagonal topologies, and in each case, we demonstrate that the final product has excellent crystallinity and porosity. The final materials contain both micro- and macropores, and the total porosity can be tuned through variation of sample annealing. Dynamic light scattering measurements reveal the presence of COF nanoparticles that grow with time at room temperature, transitioning from a homogeneous suspension to a gel. Finally, we prepare imine COF membranes and measure their rejection of polyethylene glycol (PEG) polymers and oligomers, and these measurements exhibit size-dependent rejection and adsorption of PEG solutes. This work demonstrates a versatile processing strategy to create crystalline and porous COF materials using solution processing techniques and will greatly advance the development of COFs for various applications.
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Keywords: covalent organic frameworks ; processing ; colloidal nanoparticles ; films ; membranes ; monoliths
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Pure Crystalline Covalent Organic Framework Aerogels
Dongyang Zhu ; Yifan Zhu ; Qianqian Yan ; Morgan Barnes ; Fangxin Liu ; Pingfeng Yu , et al.
Abstract: Covalent organic frameworks (COFs) are crystalline organic materials of interest for a wide range of applications due to their porosity, tunable architecture, and precise chemistry. However, COFs are typically produced in powder form and are difficult to process. Herein, we report a simple and versatile approach to fabricate macroscopic, crystalline COF gels and aerogels. Our method involves the use of dimethyl sulfoxide as a solvent and acetic acid as a catalyst to first produce a COF gel. The COF gel is then washed, dried, and reactivated to produce a pure macroscopic, crystalline, and porous COF aerogel that does not contain any binders or additives. We tested this approach for six different imine COFs and found that the crystallinities and porosities of the COF aerogels matched those of COF powders. Electron microscopy revealed a robust hierarchical pore structure, and we found that the COF aerogels could be used as absorbents in oil–water separations, for the removal of organic and inorganic micropollutants, and for the capture and retention of iodine. This study provides a versatile and simple approach for the fabrication of COF aerogels and will provide novel routes for incorporating COFs in applications that require macroscopic, porous materials.
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CAS No. : | 118727-34-7 |
Formula : | C24H21N3 |
M.W : | 351.44 |
SMILES Code : | NC1=CC=C(C2=CC(C3=CC=C(N)C=C3)=CC(C4=CC=C(N)C=C4)=C2)C=C1 |
MDL No. : | MFCD18207723 |
InChI Key : | QHQSCKLPDVSEBJ-UHFFFAOYSA-N |
Pubchem ID : | 12058813 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 27 |
Num. arom. heavy atoms | 24 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 115.96 |
TPSA ? Topological Polar Surface Area: Calculated from |
78.06 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.49 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.91 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
5.46 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.2 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.46 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.1 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.94 |
Solubility | 0.00402 mg/ml ; 0.0000114 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.25 |
Solubility | 0.00199 mg/ml ; 0.00000565 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-8.83 |
Solubility | 0.000000519 mg/ml ; 0.0000000015 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
Yes |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.67 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.05 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
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