Structure and spectroscopic characterization of tetrathia- and tetraselena[8]circulenes as a new class of polyaromatic heterocycles
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AbstractThe FTIR, Raman and UV-vis spectra of the recently synthesized tetrathia[8]circulene and tetraselena[8]circulene compounds have been measured and interpreted in details by the density functional theory (MT) calculations taking into account the molecular symmetry constrains. The structural and electronic features of the studied compounds have also been discussed in connection with the observed spectroscopic characteristics. Particularly, we have found that despite a slightly non-planar conformation the neutral tetrathia[8]circulene and tetraselena[8]circulene molecules demonstrate bifacial aromatic/antiaromatic nature. The inner octatetraene core is characterized by the presence of paratropic ("antiaromatic") ring currents, whereas the outer macrocycle constructed of benzene, thiophene or selenophene rings possesses the strong magnetically-induced diatropic ("aromatic") ring current. This fact suggests the general electronic and magnetic similarity of the tetrathia- and tetraselena[8]circulenes with the strictly planar isoelectronic tetraoxa[8]circulene and related azaoxa-derivatives discussed earlier. However, the vibrational and UV-vis absorption spectra of the studied circulenes are rather different from those of the parent tetraoxa[8]circulene which indicates a clear manifestation of the symmetry selection rules. (C) 2015 Elsevier B.V. All rights reserved.
All Author(s) ListMinaeva VA, Baryshnikov GV, Minaev BF, Karaush NN, Xiong XD, Li MD, Phillips DL, Wong HNC
Journal nameSpectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
Volume Number151
Pages247 - 261
LanguagesEnglish-United Kingdom
KeywordsCirculene, DFT calculations, Electronic transition, FT-IR spectra, Raman spectra, UV-vis spectra
Web of Science Subject CategoriesSpectroscopy

Last updated on 2020-07-07 at 00:53