Benzimidazole-Branched Isomeric Dyes: Effect of Molecular Constitution on Photophysical, Electrochemical, and Photovoltaic Properties
Journal
Journal of Organic Chemistry
Journal Volume
81
Journal Issue
2
Pages
640-653
Date Issued
2016
Author(s)
Abstract
Three benzimidazole-based isomeric organic dyes possessing two triphenylamine donors and a cyanoacrylic acid acceptor are prepared by stoichiometrically controlled Stille or Suzuki-Miyaura coupling reaction which predominantly occurs on the N-butyl side of benzimidazole due to electronic preferences. Combined with the steric effect of the N-butyl substituent, placement of the acceptor segment at various nuclear positions of benzimidazole such as C2, C4, and C7 led to remarkable variations in intramolecular charge transfer absorption, electron injection efficiency, and charge recombination kinetics. The substitution of acceptor on the C4 led to red-shifted absorption, while that on C7 retarded the charge transfer due to twisting in the structure caused by the butyl group. Because of the cross-conjugation nature and poor electronic interaction between the donor and acceptor, the dye containing triphenylamine units on C4 and C7 and the acceptor unit on C2 showed the low oxidation potential. Thus, this dye possesses favorable HOMO and LUMO energy levels to render efficient sensitizing action in solar cells. Consequently, it results in high power conversion efficiency (5.01%) in the series with high photocurrent density and open circuit voltage. The high photocurrent generation by this dye is reasoned to it exceptional charge collection efficiency as determined from the electron impedance spectroscopy. © 2015 American Chemical Society.
SDGs
Other Subjects
Charge transfer; Chemical reactions; Open circuit voltage; Solar cells; Charge collection efficiency; Charge recombination kinetics; Electronic interactions; Impedance spectroscopy; Intra-molecular charge transfer; Low oxidation potential; Photocurrent generations; Suzuki-Miyaura coupling reaction; Photovoltaic effects; benzimidazole; cyanoacrylate; dye; organic compound; absorption; Article; chemical reaction kinetics; conjugation; electrochemical impedance spectroscopy; electrochemistry; isomer; oxidation reduction potential; photochemistry; photovoltaic property; physical chemistry; Stille reaction; stoichiometry; substitution reaction; surface charge; Suzuki reaction; synthesis
Type
journal article