The formation and high stability of the H-bond-driven supramolecular architectures of the syn and anti isomers of the dioxime of bicyclo[3.3.1]nonane-3,7-dione were investigated by single crystal X-ray diffraction, NMR, FTIR, and molecular modeling. Self-assembly of the achiral syn isomer into a cyclic trimer (supramolecular wheel) and of the chiral anti isomer into homochiral cyclic dimers was observed.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo900484v | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Hydrogen-Bond-Driven Peptide Nanotube Formation: A DFT Study.
Molecules
August 2023
Department of Chemistry and Biochemistry, DePaul University, Chicago, IL 60614, USA.
DFT calculations were carried out to examine geometries and binding energies of H-bond-driven peptide nanotubes. A bolaamphiphile molecule, consisting of two N-α amido glycylglycine head groups linked by either one CH group or seven CH groups, is used as a building block for nanotube self-assembly. In addition to hydrogen bonds between adjacent carboxy or amide groups, nanotube formation is also driven by weak C-H· · ·O hydrogen bonds between a methylene group and the carboxy OH group, and between a methylene group and an amide O=C group.
View Article and Find Full Text PDFEnhanced photoinduced mass migration in supramolecular azopolymers by H-bond driven positional constraint.
J Mater Chem C Mater
September 2021
CNST@POLIMI - Fondazione Istituto Italiano di Tecnologia, Via Pascoli 70 Milan 20133 Italy
Here we investigated the role of hydrogen bonding in the design of supramolecular azopolymers with a highly directional and constrained azobenzene-chain interaction involving the aromatic ring of the photoactive molecule, by exploiting the 2-aminopyrimidine/carboxylic acid supramolecular synthon as the tool for molecular recognition. We have shown that this approach is advantageous for producing affordable and versatile photopatternable azomaterials by complexation with polyacrylic acid (PAA). Molecular model complexes were successfully prepared and characterized by X-ray diffraction analysis and FTIR spectroscopy to reveal the multiple, non-ionic interaction occurring between the azobenzene units and the polymer chains.
View Article and Find Full Text PDFA supramolecular H-bond driven light switch sensor for small anions.
Dalton Trans
January 2016
Institute for Inorganic Chemistry I, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany.
A cationic iridium complex with a 2,2'-bibenzimidazole ligand can act as a luminescent sensor for various anions. Strong H-bond supported ion pair bonding with an electron accepting dinitro-benzoate anion switches the luminescence "off". The luminescence of the sensor is switched back "on" when benzoate is replaced by competing H-bonded small anions, therefore leading to an enhanced sensitivity of the sensor system.
View Article and Find Full Text PDFModular engineering of H-bonded supramolecular polymers for reversible functionalization of carbon nanotubes.
J Am Chem Soc
October 2011
Università di Trieste, Dipartimento di Scienze Chimiche e Farmaceutiche and INSTM UdR di Trieste, Italy.
A H-bond-driven, noncovalent, reversible solubilization/functionalization of multiwalled carbon nanotubes (MWCNTs) in apolar organic solvents (CHCl(3), CH(2)Cl(2), and toluene) has been accomplished through a dynamic combination of self-assembly and self-organization processes leading to the formation of supramolecular polymers, which enfold around the outer wall of the MWCNTs. To this end, a library of phenylacetylene molecular scaffolds with complementary recognition sites at their extremities has been synthesized. They exhibit triple parallel H-bonds between the NH-N-NH (DAD) functions of 2,6-di(acetylamino)pyridine and the CO-NH-CO (ADA) imidic groups of uracil derivatives.
View Article and Find Full Text PDFH-bond-driven supramolecular architectures of the syn and anti isomers of the dioxime of bicyclo[3.3.1]nonane-3,7-dione.
J Org Chem
May 2009
Faculty of Chemistry and Chemical Engineering, Babes-Bolyai University, 11 Arany Janos, 400028, Cluj Napoca, Romania.
The formation and high stability of the H-bond-driven supramolecular architectures of the syn and anti isomers of the dioxime of bicyclo[3.3.1]nonane-3,7-dione were investigated by single crystal X-ray diffraction, NMR, FTIR, and molecular modeling.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!