Multiple-Porphyrin Functionalized Hexabenzocoronenes

Porphyrin-hexabenzocoronene architectures serve as good model compounds to study light-harvesting systems. Herein, the synthesis of porphyrin functionalized hexa-peri-hexabenzocoronenes (HBCs), in which one or more porphyrins are covalently linked to a central HBC core, is presented. A series of hexaphenylbenzenes (HPBs) was prepared and reacted under oxidative coupling conditions. The transformation to the respective HBC derivatives worked well with mono- and tri-porphyrin-substituted HPBs. However, if more porphyrins are attached to the HPB core, Scholl oxidations are hampered or completely suppressed. Hence, a change of the synthetic strategy was necessary to first preform the HBC core, followed by the introduction of the porphyrins. All products were fully characterized, including, if possible, single-crystal XRD. UV/Vis absorption spectra of porphyrin-HBCs showed, depending on the number of porphyrins as well as with respect to the substitution pattern, variations in their spectral features with strong distortions of the porphyrins' B-band.