Rectangular bimetallic diorganotin macrocycle obtained through a combination of metallosupramolecular chemistry with imine bond formation

•Diorganotin rectangle was prepared through a sequential double condensation approach.•The preparation is a very simple procedure, two steps in one pot.•The diorganotin rectangle has 17.4 Å (length) x 14.0 Å (width).•The macrocycle has a very hydrophobic cavity and form co-crystals.

Herein it is presented a combination of metallosupramolecular chemistry with imine bond formation in the one pot strategies, this is a two step multi-condensation procedure to prepare a bis-diorganotin(IV) macrocycle. First, the 2:1 condensation reaction of 3-aminobenzoic acid (1) with di-n-butyltin(IV) oxide in acetonitrile led a diorganotin(IV) building block. This followed a second step through the [2 + 2] condensation reaction with terephthalaldehyde (2) thus allowing the synthesis of a rectangular shaped 38-membered bis-iminic-diorganotin macrocycle (3). X-ray analysis of the macrocycle co-crystal with 1,3,5-trimethyltrioxane (paraldehyde) reveals a highly symmetric binuclear rectangular macrocyclic compound with approximate dimensions of 17.4 Å (length) × 14.0 Å (width).

Graphical abstractCombining metallosupramolecular chemistry with imine bond formation in a one pot two step multi-condensation procedure allows the preparation of a rectangle shaped bis-diorganotin(IV) macrocycleFigure optionsDownload full-size imageDownload as PowerPoint slide