Construction of a supramolecule comprising [2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyaninato]zinc(II) and (5,10,15,20-tetraphenylporphyrinato)zinc(II)

Abstract

The supramolecular features in the title compound, [2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyaninato]zinc(II) bis[(5,10,15,20-tetraphenylporphyrinato)zinc(II)] chloroform tetrasolvate, [Zn(C96H80N8O8)][Zn(C44H28N4)]2·4CHCl3 or [Zn(Pc)][Zn(TPP)]2·4CHCl3, result from a self-assembly of one molecule of [2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyaninato]zinc(II) (ZnPc) and two molecules of (5,10,15,20-tetraphenylporphyrinato)zinc(II) (ZnTPP). One half ZnPc, one ZnTPP and two chloroform molecules define the asymmetric unit, with the zinc(II) cation of ZnPc situated on an inversion centre. In the supramolecule, the central ZnPc moiety is sandwiched between two ZnTPPs moieties in a co-facial conformation with a π-conjugated system, leading to a nearly H-type aggregate with a distance of 3.4967 (5) Å between adjacent zinc sites. The ZnTPP units are slightly glided away to form a partial ecliptic arrangement. Each phenyl group of the TPP ligand is anchored above the N atom of the isoindole linker of the Pc ligand through weak C—H...N hydrogen bonds and is held into the crevice between the two dimethylphenoxy groups of phthalocyanine via van der Waals interactions. In the crystal, chloroform solvent molecules are situated between the supramolecules. There is another solvent-accessible void of 341 (2) Å3. The contribution of disordered solvent molecules situated in this void was removed from the diffraction data using SQUEEZE in PLATON [Spek (2015). Acta Cryst. C71, 9–18]. The given chemical formula and other crystal data do not consider this unknown solvent molecule(s).

Keywords

• crystal structure
• supramolecule
• porphyrin
• phthalocyanine
• dye-sensitized solar cells
• self-assembly
• synchrotron radiation