Abstract1,10‐Diaza‐18‐crown‐6 and 4,4′‐trimethylenedipiperidine were transformed into bis‐dithiocarbamate ligands, which were then reacted in situ with different di‐ and triorganotin(IV) chlorides to generate dinuclear monomeric or macrocyclic products. The identity of the compounds was established by elemental analysis, multinuclear NMR spectroscopy (1H, 13C, and 119Sn), IR spectroscopy, mass spectrometry, and for representative examples additionally by single‐crystal X‐ray diffraction analysis. In combination with DFT calculations, the structural characterization showed that diaryltin and dialkyltin fragments give macrocycles of different conformation owing to changes in the coordination stereochemistry (cis vs. trans isomers). The macrocycle cavities are suitable for the inclusion of guest molecules. At the supramolecular level, the Sn complex molecules are linked through intermolecular C–H···S and C–H···Cl interactions in the solid state.
Four cyclic boronate esters were synthesized by using a multicomponent reaction from (3‐aminophenyl)boronic acid, pentaerythritol, and aldehyde derivatives [isophthalaldehyde (1), dialdehyde A (2), (3‐formylphenyl)boronic acid (3), and (2,4‐difluoro‐3‐formylphenyl)boronic acid (4)]. All four reactions lead to the formation of macrocyclic compounds in good yields of more than 70 %. The cavities of the compounds consist of 29‐, 30‐ and 40‐membered rings, and the macrocyclic structures contain two (2) and four (1 and 3–4) boron atoms as Lewis acids. Additionally, the molecules contain eight (1) and six (2–4) donor atoms (N,O) within the macrocyclic structure, thus constituting a ditopic cavity. X‐ray analysis of 2 and 3 revealed the whole conformation within the trigonal planar geometry for the boron atoms and the inclusion of neutral guest molecules, chloroform for 2 and benzene for 3. Titration of the receptors with triethylamine, pyridine, and tetrabutylammonium fluoride show that the Lewis acids are available for interaction with Lewis bases. The interaction was follow by 11B NMR and UV/Vis spectroscopy.
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