1,4-Diazabicyclo[2.2.2]octane (DABCO) as a useful catalyst in organic synthesis

Baghernejad, Bita

doi:10.5155/eurjchem.1.1.54-60.2

Cited by 63 publications

(22 citation statements)

References 67 publications

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“…The maximum width of CNT was at the tip of. In contrast, the base was substantially narrower and is consistent with observations of O'Byrne et al who reported a similar phenomenon in nitrogen-doped CNT synthesized from nitrogenated precursors [23,24]. HRTEM of the CNT at the tip exhibited in Figure 1f indicates presence of highly graphitized inner 22-24 walls, whereas the outermost 3-4 walls were comparatively less graphitized, disordered with interstitial defects, which can be attributed to the 'knock-on effect' of microwave radiation, which can damage and dislodge a carbon atom from the walls of CNT [25].…”

Section: Resultssupporting

confidence: 91%

Metal Organic Frameworks Derived Fe-N-C Nanostructures as High-Performance Electrodes for Sodium Ion Batteries and Electromagnetic Interference (EMI) Shielding

Sridhar

Lee

2021

Molecules

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Metal organic framework (MOF)-derived carbon nanostructures (MDC) synthesized by either calcinations or carbonization or pyrolysis are emerging as attractive materials for a wide range of applications like batteries, super-capacitors, sensors, water treatment, etc. But the process of transformation of MOFs into MDCs is time-consuming, with reactions requiring inert atmospheres and reaction time typically running into hours. In this manuscript, we report the transformation of 1,4-diazabicyclo[2.2.2]octane, (DABCO)-based MOFs into iron nitride nanoparticles embedded in nitrogen-doped carbon nanotubes by simple, fast and facile microwave pyrolysis. By using graphene oxide and carbon fiber as microwave susceptible surfaces, three-dimensional nitrogen-doped carbon nanotubes vertically grown on reduced graphene oxide (MDNCNT@rGO) and carbon fibers (MDCNT@CF), respectively, were obtained, whose utility as anode material in sodium-ion batteries (MDNCNT@rGO) and for EMI (electromagnetic interference) shielding material (MDCNT@CF) is reported.

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Section: Resultssupporting

confidence: 91%

Metal Organic Frameworks Derived Fe-N-C Nanostructures as High-Performance Electrodes for Sodium Ion Batteries and Electromagnetic Interference (EMI) Shielding

Sridhar

Lee

2021

Molecules

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“…A polyol crosslinker and an amine catalyst were selected for their low toxicity and low vapor pressure to ensure long shelf-life stability. Specifically, glycerol is a hydrophilic trifunctional alcohol that has been shown to be a strong crosslinker in polyurethanes by ensuring high crosslinking density for the final polyurethane adhesive, while DABCO is a nontoxic, inexpensive catalyst that is highly reactive with isocyanates. , Solubilizing DABCO in glycerol yields a viscous, hydrophilic solution that is not miscible in heavy mineral oil, the chosen hydrophobic phase. Stabilizing an emulsion between DABCO/glycerol and heavy mineral oil required finding an inorganic emulsifying agent that decreased permeability and increased rigidity, as it was key to have shells that were resistant to mixing forces during fabrication but sensitive to shearing forces for deployment .…”

Section: Resultsmentioning

confidence: 99%

Rapid Underwater Adhesive Utilizing Crosslinker and Amine Catalyst-Filled Microcapsules

Messersmith

Bartlett

Rose

et al. 2021

ACS Appl. Polym. Mater.

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Rapidly curing underwater adhesives were tested on untreated substrates and demonstrated high ultimate shear strength. An isocyanate resin was combined with microcapsules containing both a polyol crosslinker and a tertiary amine catalyst. The polyurea microcapsules were synthesized on a large scale via an inverse Pickering emulsion utilizing inexpensive reagents. The microcapsules were stable to ambient conditions and gentle mixing but released their contents when appropriate shearing forces were applied. The final polyurethane adhesive achieved high bonding strength (2.88 ± 0.8 MPa) over a short time period (1 min).

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“…DABCO is often used as a base in organic synthesis [16] and is a useful synthon for supramolecular architectures [17] . DABCO forms strong halogen bonds as compared to other neutral bases, owing to the rigid pyramidal shape around the N‐atom.…”

Section: Resultsmentioning

confidence: 99%

An Insight into Non‐Covalent Interactions on the Bicyclo[1.1.1]pentane Scaffold

et al. 2020

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Bicyclo[1.1.1]pentane (BCP) is studied extensively as a bioisosteric component of drugs. Not found in nature, this molecular unit approximates the distance of a para‐disubstituted benzene which is replaced in medicines as a method of improving treatments. Predicting interactions of these drugs with specific active sites requires knowledge of the non‐covalent interactions engaged by this subunit. Structure determinations and computational analysis (Hirshfeld analysis, 2D fingerprint plots, DFT) of seven BCP derivatives chosen to probe specific and directional interactions. X‐ray analysis revealed the presence of various non‐covalent interactions including I ⋅⋅⋅ I, I ⋅⋅⋅ N, N−H ⋅⋅⋅ O, C−H ⋅⋅⋅ O, and H−C ⋅⋅⋅ H−C contacts. The preference of halogen bonding (I ⋅⋅⋅ I or I ⋅⋅⋅ N) in BCP 1–4 strictly depends upon the electronic nature and angle between bridgehead substituents. The transannular distance in co‐crystals 2 and 4 was longer as compared to monomers 1 and 3. Stronger N−H ⋅⋅⋅ O and weaker C−H ⋅⋅⋅ O contacts were observed for BCP 5 while the O ⋅⋅⋅ H interaction was a prominent contact for BCP 6. The presence of 3D BCP units prevented the π ⋅⋅⋅ π stacking between phenyl rings in 3, 4, and 7. The BCP skeleton was often rotationally averaged, indicating fewer interactions compared to bridgehead functional groups. Using DFT analysis, geometries were optimized and molecular electrostatic potentials were calculated on the BCP surfaces. These interaction profiles may be useful for designing BCP analogs of drugs.

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1,4-Diazabicyclo[2.2.2]octane (DABCO) as a useful catalyst in organic synthesis

Cited by 63 publications

References 67 publications

Metal Organic Frameworks Derived Fe-N-C Nanostructures as High-Performance Electrodes for Sodium Ion Batteries and Electromagnetic Interference (EMI) Shielding

Metal Organic Frameworks Derived Fe-N-C Nanostructures as High-Performance Electrodes for Sodium Ion Batteries and Electromagnetic Interference (EMI) Shielding

Rapid Underwater Adhesive Utilizing Crosslinker and Amine Catalyst-Filled Microcapsules

An Insight into Non‐Covalent Interactions on the Bicyclo[1.1.1]pentane Scaffold

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