Investigating the change in the photophysical properties of a trio of tetraphenylcyclopentadienone derivatives with varied groups on the aromatic rings in the 3- and 4-positions.

Organic compounds with electronic properties, such as a small band gap, are useful in areas ranging from organic field effect transistors to solar cells. Such organic compounds can possess conjugation and/or aromatic systems, with one example being tetraphenylcyclopentadienone and its derivatives. A trio of dramatically coloured tetraphenylcyclopentadienone derivatives with varied substituents on the aromatic rings in the 3- and 4-positions were prepared. Their identities were confirmed using the usual methods, for example 1 H nuclear magnetic resonance (NMR) spectroscopy, and their purity quantified using elemental analysis. The X-ray crystal structure of compound 2 was determined. Its notable structural features involved the cyclopentadienone core with its distinct C-C and C=C bond lengths and its overall nonplanarity, both of which served to mitigate its antiaromatic nature. Chloroform solutions of compounds 2-4 exhibited absorption spectra with three absorption bands at approximately 250, 350, and 500 nm that were assigned to (π)→(π*) transitions. Computational chemistry methods assisted in assigning the observed transitions to a specific molecular orbital combination in the structures of 2-4. Emission in the red end of the visible spectrum (550-625 nm) was observed from chloroform solutions of all three of the prepared compounds.