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Asymmetrically Fused Nanographene–Porphyrin Architectures

A strategy to combine three standalone aromatic building blocks in one coherent, fully conjugated molecule is presented. Namely, benzene, pyrene, and hexa‐peri‐hexabenzocoronene (HBC) are assembled around a central porphyrin core… Click to show full abstract

A strategy to combine three standalone aromatic building blocks in one coherent, fully conjugated molecule is presented. Namely, benzene, pyrene, and hexa‐peri‐hexabenzocoronene (HBC) are assembled around a central porphyrin core in an ABAC type of geometry and interconnected under oxidative Scholl conditions to achieve merging of the individual π‐systems. The three asymmetric porphyrin conjugates obtained this way exhibit intriguing absorption features, namely strongly red‐shifted and broadened spectra. The presented series of molecules demonstrates the ability to control and influence these optical properties with high precision by altering the size of the aromatic system in a controlled manner. Density functional theory calculations gave more profound insights into the electronic structure and optical transitions of the investigated fused architectures.

Keywords: asymmetrically fused; nanographene porphyrin; porphyrin; porphyrin architectures; fused nanographene; geometry

Journal Title: European Journal of Organic Chemistry
Year Published: 2024

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