Theoretical study of the effects of modifying the structures of organic dyes based on N,N-alkylamine on their efficiencies as DSSC sensitizers

Elkhattabi, Souad; Hachi, Mohamed; Fitri, Asmae; Benjelloun, Adil Touimi; Benzakour, M.; Mcharfi, Mohammed; Bouachrine, Mohammed

doi:10.1007/s00894-018-3888-0

Cited by 24 publications

(7 citation statements)

References 38 publications

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“…These dyes follow D‐π‐A structure with anchoring group as cyanoacrylic acid, the π‐bridge comprises of thiophene and oxadiazole units and carbazole as donor molecule. Benzothiadiazole and pyridine are selected to be substituted in π‐bridge of these dyes [31]. Benzothiadiazole is efficient electron taking specie, so its addition in π‐bridge enhances electron transfer process from donor to acceptor.…”

Section: Introductionmentioning

confidence: 99%

Afirst‐principlesstudy on improvement of photoinjection in organic dyes

Majid

Sana

Khan

et al. 2021

Int J of Quantum Chemistry

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First principles methods are implemented in order to design new metal free organic dyes with motivation to improve photoinjection in dye sensitized solar cell (DSSC). The simulated structures obey general D‐π‐A structure and various structural modifications are made in π‐bridge as well as donor assembly of the dyes. The addition of benzothiadiazole and pyridine in π‐bridge caused shifting of absorption spectrum of dyes shifted toward lower energies. The analysis of structural and photoelectric properties of the dyes revealed that the dyes containing triarylamine in donor assembly show largest light harvesting efficiencies. The process of photoinjection was modeled by adsorbing the series of dyes on surface of (TiO2)n particles to investigate the injection and recombination kinetics. The dyes having benzothiadiazole in π‐bridge exhibited smallest injection energies while the dyes having pyridine in the in π‐bridge shown highest recombination energies. The detailed investigation of UV‐visible spectra of dye‐semiconductor complex was carried out to explore suitability of the dyes for practical applications in DSSC.

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Section: Introductionmentioning

confidence: 99%

Afirst‐principlesstudy on improvement of photoinjection in organic dyes

Majid

Sana

Khan

et al. 2021

Int J of Quantum Chemistry

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“…Regarding D-π-A structure, several studies about dyes have been reported using different proposals. For example, modifying the donor part using coumarin [7,8], carbazole [9,10], phenothiazine [11,12], and triphenylamine [13,14]; modifying the acceptor part using cyanoacrylic acid [15] and alkoxysilane [16,17]; and mainly modifying the π-bridge using thiophene [18,19,20], benzene [21,22], dioxythiophene [23], and benzothiadiazole [24,25], among many others. Hence, the study and the understanding of the performance of D-π-A metal-free organic dyes is very important.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study of the Effect of Different π Bridges Including an Azomethine Group in Triphenylamine-Based Dye for Dye-Sensitized Solar Cells

et al. 2019

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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.

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“…37 In addition to allowing the electron to be injected into the anode quickly, the lowest occupied molecular orbital (LUMO) should be above the conduction band (CB) of TiO 2 . 38 Recent research introduced an electron auxiliary acceptor into the conjugated system between the electron-donor moiety and p-linker and used this in the design of a new architecture known as the D-A-p-A system, [39][40][41][42] where sensitizers are coupled with auxiliary acceptor units, such as quinoxaline, [43][44][45][46] benzothiadiazole, [47][48][49] thieno[3,4-c]-pyrrole-4,6dione, 50,51 benzotriazole, [52][53][54] and diketopyrrolopyrrole. 55,56 Indeed, the D-A-p-A system has shown multiple advantages, including reducing electron recombination, minimizing aggregation, adjusting the molecular energy levels, causing a red-shi of the absorption band, and increasing the photovoltaic efficiency and stability; [57][58][59] whereas several organic dyes of triphenylamine-based compounds have been used as electron donors due to the excellent light-harvesting ability of triphenylamine (TPA)-based molecules, their capacity to control the energy levels of molecules, promote charge generation, and facilitate the formation of intermolecular interactions.…”

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confidence: 99%