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New thiophene-functionalized pyrene, peropyrene and teropyrene via a two- or four-fold alkyne annulation and their photophysical properties
We synthesized thiophene-functionalized pyrene, peropyrene, and teropyrene through a two- or four-fold alkyne annulation reaction promoted by triflic acid. All of the target compounds were fully characterized spectroscopically, and the structure of the peropyrene analogue was unambiguously confirmed by X-ray crystallography. A significant red shift in the absorption and emission properties as a function of extended conjugation was observed by UV杤is and fluorescence spectroscopy. This alkyne annulation strategy is a useful method for the conversion of smaller polycyclic aromatics to larger ones, such as nanographenes.