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We have performed Density Functional Theory B3LYP/6-311++G** calculations of reaction enthalpies of antioxidant action mechanisms for nine isoflavones. O-H bond dissociation enthalpies, ionization potentials, proton dissociation enthalpies, proton affinities and electron transfer enthalpies related to Hydrogen Atom Transfer (HAT), Single Electron Transfer-Proton Transfer (SET-PT) and Sequential Proton-Loss Electron-Transfer (SPLET) mechanisms were investigated in gas- and solution-phases. Studies on the radical scavenging ability of isoflavones, contrary to various flavonoids, are still scarce. Thus, understanding of its thermodynamics can be considered beneficial. The selection of isoflavones (daidzein, formononetin, genistein, biochanin A, prunetin, 6-hydroxydaidzein, glycitein, orobol and santal) enables us to evaluate the effects of various structural features, such as the presence of methoxy (4'-OMe, 6-OMe, 7-OMe) and hydroxy (3'-OH, 5-OH, 6-OH) groups, on studied reaction enthalpies. The obtained results show that HAT can be attributed predominantly to the B ring, while SPLET takes place preferentially in the A ring, as was also indicated in experimental works.

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Three groups of naphthalene bisimides were synthesized and comparatively studied, namely, alkyl bisimides, alkylaryl ones, and novel bisimides containing the alkylthienyl moiety in the N-substituent. The experimental absorption spectra measured in CHCl(3) exhibit one intensive absorption band that is uniformly detected in the spectral range of 340 to 400 nm for all studied molecules. This band consists of three or four vibronic peaks. The introduction of an alkylthienyl group results in the appearance of an additional band (in the spectral range from 282 to 326 nm, depending on the position of the substituent) that can be ascribed to the pi-pi* transition in the thienyl chromophore. The minimal substituent effect on the lowest electronic transitions was explained using the quantum chemical calculations based on the time-dependent density functional theory. The investigation of the shapes of frontier orbitals have also shown that the oxidation of bisimides containing thiophene moiety is primary connected with the electron abstraction from the thienyl ring. To the contrary, the addition of an electron in the reduction process leads to an increase in the electron density in the central bisimide core. As shown by the electrochemical measurements, the onset of the first reduction potential (so-called "electrochemically determined LUMO level") is sensitive toward the type of the substituent being shifted from about -3.72 eV for bisimides with alkyl substituents to about -3.83 eV for alkylaryl ones and to about -3.94 eV for bisimides with thienyl groups. The presence of the thienyl ring also lowers the energy difference between the HOMO and LUMO orbitals. These experimental data can be well correlated with the DFT calculations in terms of HOMO/LUMO shapes and energies. Taking into account the low position of their LUMO level and their highly ordered supramolecular organization, the new bisimides are good candidates for the use in n-channel field effect transistors, operating in air. The fabricated "all organic" transistors show effective charge carrier mobilities in the range 10(-2) to 10(-4) cm(2) V(-1) s(-1) and the ON/OFF ratios exceed 10(5) for the majority of cases.