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Multiple‐porphyrin functionalized hexabenzocoronenes

DOI: 10.1002/chem.201903113 DOI Help

Authors: Norbert Jux (Friedrich-Alexander-University Erlangen-Nürnberg) , Max M. Martin (Friedrich-Alexander-University Erlangen-Nürnberg) , Dominik Lungerich (Friedrich-Alexander-University Erlangen-Nürnberg) , Frank Hampel (Friedrich-Alexander-University Erlangen-Nürnberg) , Jens Langer (Friedrich-Alexander-University Erlangen-Nürnberg) , Tanya K. Ronson (University of Cambridge)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Chemistry – A European Journal

State: Published (Approved)
Published: August 2019
Diamond Proposal Number(s): 11397

Open Access Open Access

Abstract: Porphyrin‐hexabenzocoronene architectures serve as good model compounds to study light harvesting systems. Herein, the synthesis of porphyrin functionalized hexa‐peri‐hexa‐benzocoronenes (HBCs), in which one or more porphyrins are covalently linked to a central HBC core, is presented. Therefore, a series of hexaphenylbenzenes (HPBs) was prepared and reacted under oxidative Scholl 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 pre‐forming 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.

Journal Keywords: nanographene; hexabenzocoronene; porphyrinoids; nanostructures; Scholl oxidation

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction