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The impact of the alkyl chain on the nitrogen atomN-ethyl, N-butyl, N-octyl, and N-dodecylin phenothiazines with bis-2-cyanoacrylic acid units on the optical and electrochemical behavior and finally photovoltaic response of DSSCs sensitized with such dyes was investigated. Such compounds as alternatives to ruthenium-based dyes were evaluated. The optical properties of the phenothiazine derivatives were studied by UV–vis and photoluminescence measurements in various solutions. Additionally, electronic absorption spectra of dyes anchored to TiO2 were registered. Electrochemical properties were studied by using cyclic and differential pulse voltammetry. Experimental data and the adsorption energies of dyes@TiO2 were supported by DFT and TD-DFT calculations. DSSCs consisting of a TiO2 anode sensitized with prepared dyes, I–/I3 – electrolyte, and Pt/FTO counter electrode were fabricated. The idea of dye cocktail utilization was also developed. The prepared solar cells were characterized via current–voltage, transient absorption, and electrochemical impedance spectroscopy measurements. Transient absorption spectroscopy revealed a positive effect of the alkyl chain length and cocktail dye configuration on the efficiency of the fast electron transfer processes.