The FTIR spectra of substituted tetraoxa[8]circulenes and their assignments based on DFT calculations

The FTIR spectrum of symmetrical derivative of the tetraoxa[8]circulene, named para-dinaphthyleno-2,3,10,11-tetraundecyldiphenylenotetrafuran (p-2B2N4R, R = n-C11H23) has been recorded and interpreted using density functional theory (DFT) calculations for the model compounds p-2B2N4R (R = H, C2H5). The unsubstituted tetraoxa[8]circulene, namely para-dinaphthylenodiphenylenotetrafuran (p2B2N) and para-dinaphthyleno-2,3,10,11-tetraethyldiphenylenotetrafuran (p-2B2N4R, R = C2H5) belong to the D-2h and D-2 symmetry point groups, respectively. The equilibrium molecular geometry, harmonic vibrational frequencies and infrared intensities have been calculated utilizing the DFT/B3LYP method with the 6-31G(d) basis set using the symmetry constraints. Comparison of the calculated vibrational spectra with the experimental data provides a reliable assignment of the observed bands in the FTIR spectra. The results of quantum-chemical calculations provide a complete interpretation of vibrational modes based on a good agreement with all details of the experimental spectra. (c) 2013 Elsevier B.V. All rights reserved.