Molecular Design of D-π-A-A Organic Dyes Based on Triphenylamine Derivatives with Various Auxiliary Acceptors for High Performance DSSCs

Slimi, Ahmed; Fitri, Asmae; Benjelloun, Adil Touimi; Elkhattabi, Souad; Benzakour, M.; Mcharfi, Mohammed; Bouachrine, Mohammed

doi:10.1007/s11664-019-07228-0

Cited by 29 publications

(9 citation statements)

References 63 publications

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“…At present, density functional theory (DFT) and time-dependent density functional theory (TD-DFT) are the most widely used methods in computational simulation of the photophysical properties of organic small molecules and can predict and explain the properties of these molecules reasonably well. [13][14][15][16][17][18][19][20] For molecules with intramolecular charge transfer or charge separation, due to the complexity of the intramolecular electronic behavior, there may be discrepancies between the calculations and experiments; nonetheless, calculations still play an important role in molecular design and guiding experiments. [21][22][23][24] Long-range correction functionals were found to be more effective at solving the charge-transfer issue.…”

Section: Mtpapa-apycmentioning

confidence: 99%

“…The photophysical properties of dye molecules can be improved by introducing different donor, acceptor, and π bridging groups, or by modifying the molecular structure with different substituents and heterocycles. [18][19][20][25][26][27][28][29] Since heterocycles are less aromatic than benzene and polycyclic hydrocarbon, the introduction of a heterocyclic ring between the donor and the acceptor can increase the intramolecular charge transfer. [30][31][32][33][34][35][36] The enhanced conjugation between the donor and acceptor is disadvantageous for the separation of charges within the molecule, and thus it is necessary to interrupt the interaction between the donor and the acceptor.…”

Section: Mtpapa-apycmentioning

confidence: 99%

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Effects of heterocyclic ring and amino‐ethyl‐amino group on the electronic and photophysical properties of a triphenylamine‐pyrimidine dye

Yang

Liu

Lü

et al. 2020

Int J of Quantum Chemistry

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Introduction of a heterocyclic ring and an amino‐ethyl‐amino group to donor‐acceptor (D‐A) type photosensitive dyes can modulate the lifetime of the charge separation generated in the D‐A dyes as well as their electronic and UV‐vis absorption properties. Here we perform density functional theory (DFT) and time‐dependent density functional theory (TD‐DFT) calculations to study 11 derivatives of a triphenylamine‐pyrimidine, namely MTPA‐Pyc, in order to improve the performance of MTPA‐Pyc as solar cell sensitizers. Five heterocyclic rings and an amino‐ethyl‐amino group were introduced on the styryl moiety of MTPA‐Pyc. The results show that the introduction of heterocyclic rings generally causes an absorption red shift, but the absorption intensity reduces as a result of the increase in the dihedral angle between the donor and acceptor. Further, introduction of an amino‐ethyl‐amino group to these dyes with a heterocyclic ring modification disrupts the conjugation between the donor and acceptor, which does not benefit the absorption but may have the potential to increase the lifetime of charge separation of the dyes. We identify 2 out of 11 dyes that have the best potential for solar cell applications.

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Section: Mtpapa-apycmentioning

confidence: 99%

Section: Mtpapa-apycmentioning

confidence: 99%

Effects of heterocyclic ring and amino‐ethyl‐amino group on the electronic and photophysical properties of a triphenylamine‐pyrimidine dye

Yang

Liu

Lü

et al. 2020

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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“…The basic purposes of the dyes are absorption of light and transfer of charge, which are strongly dependent on their structure and electronic properties. [10] There have been a variety of donor groups, such as phenothiazine, [11,12] carbazole, [13,14] triphenylamine, [15] and coumarin. [16] Efficient acceptors include alkoxysilane [17] and cyanoacrylic acid, [18] whereas the π-spacer could have units of different organic groups, including dioxythiophene, [19] benzene, [20] benzothiadiazole, [21] and thiophene.…”

mentioning

confidence: 99%

“…[23] There have been numerous attempts to tune the properties of photosensitizers with different configurations. [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] The modifications in the configuration of the dyes, using different donors, acceptors, and spacers, appeared to change their efficiencies. The π-bridge length of organic dyes greatly affects the molecular structure, which causes changes in band gaps, emission spectra, and optoelectronic properties.…”

mentioning

confidence: 99%

Time‐dependent density functional theory investigations on structural modification in carbazole‐based organic photosensitizers to improve electron injection in dye‐sensitized solar cell

Majid

Sana

Khan

et al. 2020

Int J of Quantum Chemistry

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The time‐dependent density functional theory approach, implemented at hybrid‐B3LYP, GGA‐PBE, and density functional‐based tight binding levels of theory, was used to model photoinjection in organic dye/TiO2 quantum dot to explore the prospects of improvement of dye‐sensitized solar cell (DSSC). The photosensitizer used in this study consisted of six carbazole‐based organic dyes, a cyanoacrylic acid group as an acceptor and an oligothiophene π‐bridge spacer. The modifications were made in the dyes by increasing the length of the spacer by adding thiophene and oxadiazole rings at different positions of the donor‐acceptor bridge. The structural variations appeared to alter the electronic and optical properties of dyes studied via energy levels and excitation spectra. The UV‐Vis spectra calculated for all the dyes in solvents exhibited a red shift in spectral peaks with an increase in the polarity of the solvents. The findings of the study pointed toward the indirect photoinjection of the dye‐(TiO2)96 complex for six different dyes. The substitution of the oxadiazole ring at the center and addition of a thiophene ring at the edge of the spacer produced two dyes that exhibited the lowest injection energies of 0.11 and 0.17 eV, along with the regeneration energies of 1.18 and 1.12 eV, respectively. The dyes reported here may have promising applications in photoanode for enhancing the performance of DSSC.

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Molecular Design of D-π-A-A Organic Dyes Based on Triphenylamine Derivatives with Various Auxiliary Acceptors for High Performance DSSCs

Cited by 29 publications

References 63 publications

Effects of heterocyclic ring and amino‐ethyl‐amino group on the electronic and photophysical properties of a triphenylamine‐pyrimidine dye

Effects of heterocyclic ring and amino‐ethyl‐amino group on the electronic and photophysical properties of a triphenylamine‐pyrimidine dye

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

Time‐dependent density functional theory investigations on structural modification in carbazole‐based organic photosensitizers to improve electron injection in dye‐sensitized solar cell

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