Triskelion-Shaped Hexabenzocoronenes: Synthesis and Characterization of Tris-Substituted HBC Derivatives
Buck J, Hampel F, Hirsch A (2025)
Publication Type: Journal article
Publication year: 2025
Journal
Book Volume: 31
Article Number: e202404000
Journal Issue: 5
DOI: 10.1002/chem.202404000
Abstract
The synthesis of unprecedented triskelion-shaped hexa-peri-hexabenzocoronenes with C3, C3h or D3h symmertry is reported. We present a new, five step synthetic access to tris-iodinated HBC derivatives carrying different solubilizing moieties (tert-butyl and mesityl), which serve as suitable building blocks for further functionalization. These molecules can undergo Sonogashira cross coupling reactions to obtain a series of seven ethynyl tris-substituted HBCs. The coupling partners range from carbon-based aromatic scaffolds (tBu-benzene, naphthalene, phenanthrene) to ligands for metal complexes (bipyridine, phenanthroline, terpyridine, acetylacetone). The optoelectronic properties were investigated by UV/vis absorption spectroscopy resulting in a significant bathochromic shift of the absorption maximum compared to the iodinated starting material. Semiempirical calculations were used to determine the conformation and symmetry of the compounds.
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How to cite
APA:
Buck, J., Hampel, F., & Hirsch, A. (2025). Triskelion-Shaped Hexabenzocoronenes: Synthesis and Characterization of Tris-Substituted HBC Derivatives. Chemistry - A European Journal, 31(5). https://doi.org/10.1002/chem.202404000
MLA:
Buck, Janina, Frank Hampel, and Andreas Hirsch. "Triskelion-Shaped Hexabenzocoronenes: Synthesis and Characterization of Tris-Substituted HBC Derivatives." Chemistry - A European Journal 31.5 (2025).
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