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Synthesis and Properties of Cycloparaphenylene-2,7-pyrenylene: A Pyrene-Containing Carbon Nanoring

Akiko Yagi, Gandikota Venkataramana, Yasutomo Segawa, and Kenichiro Itami

Chem. Commun. 2013, Accepted Manuscript, doi: 10.1039/C3CC48198K


The first synthesis of a pyrene-containing carbon nanoring, cyclo[12]paraphenylene[2]-2,7-pyrenylene ([12,2]CPPyr), is described. Through a sequence of stepwise macrocyclization using Pd and Ni catalysts followed by aromatization of L-shaped cyclohexane units afforded a [12,2]CPPyr in five steps from commercially available compounds. The UV-vis absorption and fluorescence spectra as well as TD-DFT calculations clarified the unique photophysical and electronic properties of a [12,2]CPPyr.

 

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