Arnoldo Orozco, Kole Joachim, Henry D Ruiz
Aug 29, 2020
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Journal
Luminescence : the journal of biological and chemical luminescence
Abstract
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 it's derivatives. A trio of dramatically colored tetraphenylcyclopentadienone derivatives with varied substituents on the aromatic rings in the 3- and 4-position were prepared. Their identities were confirmed by the usual methods, for example, 1 H NMR spectroscopy, and their purity quantified by elemental analysis. The x-ray crystal structure of compound 2 was determined. It's notable structural features involved the cyclopentadienone core with it's distinct C-C and C=C bond lengths and it's overall nonplanarity, both of which served to mitigate it's 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 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.