Functionalized cylopenta[hi]aceanthrylenes (compound 3) and dicyclopenta[de,mn]tetracenes (compound 7) are electron acceptor materials derived from fullerene and inspired by the challenge of tuning the chemical, conductive and electronic properties of fullerene derivatives. These two compounds were studied In silico to gain a better understanding of their properties at molecular level. DFT and TDDFT in Gaussian 09 Software were used for geometry optimization, molecular orbital study and absorption spectrum prediction. Five (5) different functionals namely B3LYP, CAM-B3LYP, PBE, HCTH and TPSS with 6-311g (d,p) and aug-cc-pvdz basis sets were employed in the calculations. Among the ten (10) pairs of functionals and basis set employed, B3LYP functional combined with 6-311g(d,p) basis best predicted the HOMO-LUMO band gap and the absorption spectrum of the two compounds in comparison to experimental results. The calculated HOMO-LUMO band gap for compounds 3 and 7 are 1.88 eV and 1.83 eV and first transition state absorption peaks are at 862 nm and 820 nm respectively. Experimentally, the functionalized compounds both exhibit a green color having optical band gaps of 1.52 eV and 1.51 eV and visible region absorption peak at 693 nm and with slight difference UV region absorption peaks. Molecular orbital study reveals that the 693 nm peak is mainly caused by HOMO-LUMO excitation where the electron density shifts from being distributed evenly in the entire molecule to the highly conjugated center which has the cyclopenta[hi]aceanthrylenes or dicyclopenta[de,mn]tetracenes.

DFT and TDDFT studies of functionalized cyclopenta[hi]aceanthrylenes and dicyclopenta[de,mn]tetracenes

247th National Meeting (2014)

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