Abstract
Ten molecules were theoretically calculated and studied through density functional theory with the M06 density functional and the 6-31G(d) basis set. The molecular systems have potential applications as sensitizers for dye-sensitized solar cells. Three molecules were taken from the literature, and seven are proposals inspired in the above, including the azomethine group in the π-bridge expecting a better charge transfer. These molecular structures are composed of triphenylamine (donor part); different combinations of azomethine, thiophene, and benzene derivatives (π-bridge); and cyanoacrylic acid (acceptor part). This study focused on the effect that the azomethine group caused on the π-bridge. Ground-state geometry optimization, the highest occupied molecular orbital, the lowest unoccupied molecular orbital, and their energy levels were obtained and analyzed. Absorption wavelengths, oscillator strengths, and electron transitions were obtained via time-dependent density functional theory using the M06-2X density functional and the 6-31G(d) basis set. The free energy of electron injection (ΔGinj) was calculated and analyzed. As an important part of this study, chemical reactivity parameters are discussed, such as chemical hardness, electrodonating power, electroaccepting power, and electrophilicity index. In conclusion, the inclusion of azomethine in the π-bridge improved the charge transfer and the electronic properties of triphenylamine-based dyes.
Highlights
Solar energy is a form of renewable energy, being the most abundant on this planet and, generating great interest to transform solar energy into electrical energy while being friendly to the environment
Silicon-based solar cells and dye-sensitized solar cells (DSSC) are some more developed devices for their promising efficiency; from the above, DSSCs have presented a great growth in efficiency in a short time
Stokes shift can be consulted in the Supplementary Material; the results indicate that the studied molecules constitute potential applications in organic light-emitting diodes (OLEDs), except TPAZ1 linking the azomethine group with the donor moiety
Summary
Solar energy is a form of renewable energy, being the most abundant on this planet and, generating great interest to transform solar energy into electrical energy while being friendly to the environment. Seven dyes with D-π-A structure were conformed by triphenylamine (TPA) in the donor part; cyanoacrylic acid in the acceptor part; and different conformations in the π-bridge using thiophene, benzene, methylbenzene, nitrobenzene, and azomethine groups. These dyes were inspired by three experimentally reported dyes, which are 2-Cyano-3-(5-(4-(diphenylamino)phenyl)thiophen-2-yl)acrylic acid [40], 2-Cyano-3-[5-[40 -(diphenylamino)[1,10 -biphenyl]-2-thienyl]-2-acrylic acid [41,42], and 2-Cyano-3-[50 -[4-(diphenylamino)phenyl][2,20 -bithiophen]-5-yl]-2-acrylic acid [41,43,44]. The best sensitizers were chosen regarding their optoelectronic properties
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