The proposed project combines recent advancements in supramolecular porphyrin systems and polyyne chemistry to create and study novel hybrid compounds: carbo-porphyrin nanorings. This will include extensive synthetic work to find the most efficient working schemes for macrocyclic compounds with varying sizes and different peripheral substituents, while minimizing linear polymerization. Specific choice of the building blocks will be guided by computer-aided design to ensure appropriate connectivity and steric demands for subsequent cyclooligomerizations. The size selectivity will be further refined by using template-assisted covalent self-assembly utilizing differently coordinating templates. The electronic and magnetic nature of the target compounds will be studied in solution using a range of techniques, including Nuclear Magnetic Resonance spectroscopy, UV-vis-NIR absorption and fluorescence spectroscopy and electrochemical methods, additionally characterized with X-ray crystallography in the solid state. These efforts will be focused on exploring global aromatic and antiaromatic currents in the neutral and oxidized forms of the macrocycles, gaining insight into the nature of aromaticity in nanometer-size pi-conjugated systems and contributing to the design of future functional materials.
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