The tripodal system 4, in which urea fragments are appended to the three terminal amine nitrogen atoms of a tris(2-aminoethyl)amine (tren) subunit, includes a Cu(II) ion and two anions X-, according to a cascade mechanism through three well defined stepwise equilibria in a DMSO solution. The first anion X- (halide, N3-, NCS-, NO2-, H2PO4-) seeks the Cu(II) centre coordinated by the tren moiety; the second anion X- interacts with the trisurea cavity, but this occurs only if the stronger H-bond acceptors, such as N3- and H2PO4-, are used. Binding of the second X- ion is favoured by the preorganising effect exerted by the metal and disfavoured by the steric and electrostatic repulsions between the anions. Under the appropriate conditions, heterodinuclear complexes of formula [Cu(II)(4)(Cl)(H2PO4)] can be obtained in solution, in which Cl- is bound to the metal centre and H2PO4- interacts with the trisurea compartment.
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http://dx.doi.org/10.1002/chem.200601682 | DOI Listing |
Molecules
August 2024
Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi'an 710069, China.
Herein, we report a new strategy for the design of antibiotic agents based on the electrostatic interaction and hydrogen bonding, highlighting the significance of hydrogen bonding and the increased recognition sites in facilitating the interaction with bacterial cell membranes and DNA. A series of quaternary ammonium functionalized urea-based anion receptors were studied. While the monodentate mono-urea , bisurea , and trisurea failed to break through the cell membrane barrier and thus could not kill bacteria, the extended bidentate dimers - presented gradually increased membrane penetrating capabilities, DNA conformation perturbation abilities, and broad-spectrum antibacterial activities against , , , , and .
View Article and Find Full Text PDFChemistry
May 2024
Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstraße 10, 07743, Jena, Germany.
Hydrogen bonds are a versatile tool for creating fibrous, bottlebrush-like assemblies of polymeric building blocks. However, a delicate balance of forces exists between the steric repulsion of the polymer chains and these directed supramolecular forces. In this work we have systematically investigated the influence of structural parameters of the attached polymers on the assembly behaviour of benzene trisurea (BTU) and benzene tris(phenylalanine) (BTP) conjugates in water.
View Article and Find Full Text PDFACS Macro Lett
July 2021
Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstraße 10, 07743 Jena, Germany.
Strong directional hydrogen bonds represent a suitable supramolecular force to drive the one-dimensional (1D) aqueous self-assembly of polymeric amphiphiles resulting in cylindrical polymer brushes. However, our understanding of the kinetics in these assembly processes is still limited. We here demonstrate that the obtained morphologies for our recently reported benzene tris-urea and tris-peptide conjugates are strongly pathway-dependent.
View Article and Find Full Text PDFAn amphiphilic tris-urea compound (1) containing hydrophilic resorcinol units was designed and synthesized. Compound 1 formed supramolecular hydrogels in basic buffers, such as glycine-NaOH, phosphate-NaOH, 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES)-NaOH, and borate-NaOH. The optimum pH range of the buffer solution for gelation was 10-11 and insoluble suspensions or solutions were formed when the pH was outside this range.
View Article and Find Full Text PDFChemistry
January 2020
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of, the Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi'an, 710127, P. R. China.
Charge-transfer (CT) complexes, formed by noncovalent bonding between electron-rich (donor, D) and electron-deficient (acceptor, A) molecules (or moieties) have attracted considerable attention due to their fascinating structures and potential applications. Herein, we demonstrate that anion coordination is a promising strategy to promote CT complex formation between anion-binding, electron-rich tris(urea) donor ligands (D) and electron-deficient viologen cation acceptors (A), which form co-crystals featuring infinite ⋅⋅⋅DADA⋅⋅⋅ or discrete (circular DADA or three-decker DAD) π-stacking interactions. These CT complexes were studied by X-ray diffraction, UV/Vis spectroscopy, electric conductivity measurements, charge displacement curve (CDC) calculations, and DFT computations.
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