- Award ID(s):
- 1900100
- NSF-PAR ID:
- 10173203
- Date Published:
- Journal Name:
- New Journal of Chemistry
- Volume:
- 43
- Issue:
- 44
- ISSN:
- 1144-0546
- Page Range / eLocation ID:
- 17174 to 17181
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
More Like this
-
null (Ed.)Three nitrogen-rich heterocyclic compounds containing the diamino-pyrimidine mono- N -oxide moiety were synthesized via mild oxidation reactions. Oxidation of the furazano-pyrimidine compound ( 1 ) with a mixture of trifluoroacetic anhydride (TFAA) and hydrogen peroxide (50%) gave the nitrate salt ( 3 ). All of the compounds were characterized by NMR spectra, elemental analysis, and single-crystal X-ray diffraction. They show high thermal stability and good detonation performance as well as low sensitivity.more » « less
-
Abstract Cocrystallizations of diboronic acids [1,3‐benzenediboronic acid (1,3‐bdba), 1,4‐benzenediboronic acid (1,4‐bdba) and 4,4’‐biphenyldiboronic acid (4,4’‐bphdba)] and bipyridines [1,2‐bis(4‐pyridyl)ethylene (bpe) and 1,2‐bis(4‐pyridyl)ethane (bpeta)] generated the hydrogen‐bonded 1 : 2 cocrystals [(1,4‐bdba)(bpe)2] (1), [(1,4‐bdba)(bpeta)2] (2), [(1,3‐bdba)(bpe)2(H2O)2] (3) and [(1,3‐bdba)(bpeta)2(H2O)] (4), wherein 1,3‐bdba involved hydrated assemblies. The linear extended 4,4’‐bphdba exhibited the formation of 1 : 1 cocrystals [(4,4'‐bphdba)(bpe)] (5) and [(4,4'‐bphdba‐me)(bpeta)] (6). For 6, a hemiester was generated by an in‐situ linker transformation. Single‐crystal X‐ray diffraction revealed all structures to be sustained by B(O)−H⋅⋅⋅N, B(O)−H⋅⋅⋅O, Ow−H⋅⋅⋅O, Ow−H⋅⋅⋅N, C−H⋅⋅⋅O, C−H⋅⋅⋅N, π⋅⋅⋅π, and C−H⋅⋅⋅π interactions. The cocrystals comprise 1D, 2D, and 3D hydrogen‐bonded frameworks with components that display reactivities upon cocrystal formation and within the solids. In 1 and 3, the C=C bonds of the bpe molecules undergo a [2+2] photodimerization. UV radiation of each compound resulted in quantitative conversion of bpe into cyclobutane tpcb. The reactivity involving 1 occurred via 1D‐to‐2D single‐crystal‐to‐single‐crystal (SCSC) transformation. Our work supports the feasibility of the diboronic acids as formidable structural and reactivity building blocks for cocrystal construction.
-
null (Ed.)The molecular structure of trans -bis(pyridin-3-yl)ethylene ( 3,3′-bpe ), C 12 H 10 N 2 , as determined by single-crystal X-ray diffraction is reported. The molecule self-assembles into two dimensional arrays by a combination of C—H...N hydrogen bonds and edge-to-face C—H... π interactions that stack in a herringbone arrangement perpendicular to the crystallographic c -axis. The supramolecular forces that direct the packing of 3,3′-bpe as well as its packing assembly within the crystal are also compared to those observed within the structures of the other symmetrical isomers trans -1,2-bis( n -pyridyl)ethylene ( n , n ′-bpe , where n = n ′ = 2 or 4).more » « less
-
Abstract Various robust, crystalline, and porous organic frameworks based on in situ‐formed imine‐linked oligomers were investigated. These oligomers self‐assembled through collaborative intermolecular hydrogen bonding interactions via liquid–liquid interfacial reactions. The soluble oligomers were kinetic products with multiple unreacted aldehyde groups that acted as hydrogen bond donors and acceptors and directed the assembly of the resulting oligomers into 3D frameworks. The sequential formation of robust covalent linkages and highly reversible hydrogen bonds enforced long‐range symmetry and facilitated the production of large single crystals, with structures that were unambiguously determined by single‐crystal X‐ray diffraction. The unique hierarchical arrangements increased the steric hindrance of the imine bond, which prevented attacks from water molecules, greatly improving the stability. The multiple binding sites in the frameworks enabled rapid sequestration of micropollutant in water.
-
Abstract Various robust, crystalline, and porous organic frameworks based on in situ‐formed imine‐linked oligomers were investigated. These oligomers self‐assembled through collaborative intermolecular hydrogen bonding interactions via liquid–liquid interfacial reactions. The soluble oligomers were kinetic products with multiple unreacted aldehyde groups that acted as hydrogen bond donors and acceptors and directed the assembly of the resulting oligomers into 3D frameworks. The sequential formation of robust covalent linkages and highly reversible hydrogen bonds enforced long‐range symmetry and facilitated the production of large single crystals, with structures that were unambiguously determined by single‐crystal X‐ray diffraction. The unique hierarchical arrangements increased the steric hindrance of the imine bond, which prevented attacks from water molecules, greatly improving the stability. The multiple binding sites in the frameworks enabled rapid sequestration of micropollutant in water.