6533b838fe1ef96bd12a530d
RESEARCH PRODUCT
One-Pot Synthesis and AFM Imaging of a Triangular Aramide Macrocycle
Andreas F. M. KilbingerAngelika KühnleThomas BallyTomáš ŠOlomekMichael BadouxChristopher M. HaukeChristof Storzsubject
Bridged-Ring CompoundsModels MolecularMacrocyclic CompoundsSurface PropertiesStereochemistryOne-pot synthesisSupramolecular chemistryMicroscopy Atomic Force010402 general chemistry53001 natural sciencesBiochemistryCatalysisCalcium CarbonateColloid and Surface ChemistrySide chainCombinatorial Chemistry TechniquesMoleculeProtecting groupbiology010405 organic chemistryHydrogen bondChemistryAryleneHydrogen BondingGeneral Chemistrybiology.organism_classificationAramides0104 chemical sciencesCrystallographyCyclizationBenzamidesDimerizationdescription
Macrocyclizations in exceptionally good yields were observed during the self-condensation of N-benzylated phenyl p-aminobenzoates in the presence of LiHMDS to yield three-membered cyclic aramides that adopt a triangular shape. An ortho-alkyloxy side chain on the N-benzyl protecting group is necessary for the macrocyclization to occur. Linear polymers are formed exclusively in the absence of this Li-chelating group. A model that explains the lack of formation of other cyclic congeners and the demand for an N-(o-alkoxybenzyl) protecting group is providedon the basis of DFT calculations.High-resolution AFM imaging of the prepared molecular triangles on a calcite(10.4) surface shows individual molecules arranged in groups of four due to strong surface templating effects and hydrogen bonding between the molecular triangles.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-01-01 |