A computational approach on engineering short spacer for carbazole-based dyes for dye-sensitized solar cells

Kandregula, Ganapathi Rao; Mandal, Sudip; Mirle, Chinmaya; Ramanujam, Kothandaraman

doi:10.1016/j.jphotochem.2021.113447

Cited by 12 publications

(3 citation statements)

References 76 publications

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“…Triphenylamine and its analogous such as carbazole and indoline have been extensively studied as metal-free sensitizers for their excellent hole mobility, isotropic charge transport and other interesting properties. 2,16,[22][23][24][25][26][27][28][29][30][31] Moreover, these functional structures show excellent electron-donating ability and have been widely used as donors in the design and synthesis of various D-π-A type dyes. [32][33][34][35][36][37][38][39][40] Compared with organometallic dyes, the internal charge transfer in triphenylamine-based dye lead to a broaden UV-vis absorption spectrum, a lower HOMO energy level and a smaller HOMO-LUMO energy gap, which make these sensitizers more efficient in the application in DSSCs.…”

Section: Introductionmentioning

confidence: 99%

Tuning the HOMO Energy of the Triarylamine Molecules with Orthogonal HOMO and LUMO Using Functional Groups

Zhuang

Amaro

Testoff

et al. 2023

Preprint

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Tuning the HOMO and LUMO energy strategically of triphenylamine derivatives plays an important role towards understanding and design of high performance organic photovoltaics. To improve on the charge separation and electron transfer properties, twenty one D-pi-A organic dyes with nitrostyryl triphenylamine-based structures (NTPAs) were designed and computationally studied, in which triphenylamine, carbazole, or indoline structures were used as donor and NO2 group as acceptor. The LUMOs of these dyes are more localized at the nitrostyryl moiety with almost the same energy and the HOMOs, which are orthogonal to the LUMOs, can be conveniently tuned by changing the donor structure and using different functional groups substituted on the donor. Compared with triphenylamine molecules, carbazole molecules decrease the HOMO energy of NTPA, whereas cis N-phenylindoline structure increase the HOMO energy. In addition, the exciton sizes generated by these dyes are also tuned in a range of 7.0-12.7 A. These results show that introduction of dimethylamino group on the triphenylamine moiety greatly increases the HOMO energy and prolongs the maximum absorption wavelength as well as increases the exciton size, indicating that NTPA dyes containing strong electron donating dimethylamino group on the donor part are promising candidates as sensitizers in the dye-sensitized solar cell applications. The results of the structural and spectral properties show good correlation with the experimental results, which confirms that the DFT method employed in this work is an effective way to design organic small molecule based sensitizers.

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Section: Introductionmentioning

confidence: 99%

Tuning the HOMO Energy of the Triarylamine Molecules with Orthogonal HOMO and LUMO Using Functional Groups

Zhuang

Amaro

Testoff

et al. 2023

Preprint

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“…Organic small molecules have been studied extensively due to their many applications, such as in solar cells 7,[31][32][33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49] and other fields. 2,[50][51][52][53][54][55][56][57][58][59][60][61][62][63][64][65][66][67] These wide applications are due to their facile synthesis and versatile tuning ability to meet specific requirements.…”

Section: Introductionmentioning

confidence: 99%

DFT studies of proton transfer of 2, 4-dihydroxybenzoic acid derivatives

Bridgmohan

Wang

2023

Preprint

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In this work, the proton transfer and photophysical properties of 2,4-dihydroxybenzoic acid and its chlorinated and brominated derivatives were studied using Density Functional Theory (DFT) to understand the proton transfer mechanism of these molecules as matrices in matrix-assisted laser desorption-ionization (MALDI). Structures, IR, UV-Vis, and fluorescence spectra were obtained together with the energies of frontier orbitals from DFT and time-dependent DFT calculations. In addition, the proton affinity (PA) and gas phase acidity (GPA) of the molecules were determined to understand the heavy atom substitution effect. Upon substitution of Cl and Br, the UV-Vis absorption at ~330 nm increases with heavy atom substitutions. While no apparent change in the OH bond strength at the ground state, it is substantially weakened upon electronic excitation at both the first singlet and triplet excited states under heavy atom substitution. These results demonstrate that both the UV-Vis absorption and intersystem crossing play important roles in facilitating proton transfer in heavy atom substitution of 2,4-dihydroxybenzoic acid.

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“…[1][2][3][4][5][6][7][8][9][10][11][12] To improve the efficiency of organic photovoltaic (OPV) cells, various new design strategies have recently been developed. [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] For example, Cnops et al improved the small-molecule OPV efficiencies to 8.5% by exploiting long-range exciton energy transfer. 13 We recently demonstrated efficiency improvements in OPVs that incorporate two electron acceptors to form a cascading donor-acceptor1-acceptor2 architecture 14,29 as well as charge-separated sensitizers.…”

Section: Introductionmentioning

confidence: 99%

Electron Acceptability of Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons: Effect of One Electron

Ubaldo

Colley

Plunkett

et al. 2022

Preprint

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To accurately predict the electron acceptability of cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs), we evaluated the performance of six functionals, B3LYP, CAM-B3LYP, HSEH1PBE, PBE, TPSS, and HCTH, using eight CP-PAHs. The results show that B3LYP is the best to obtain the energy of the highest occupied molecular orbital (HOMO), the energy of the lowest unoccupied molecular orbital (LUMO), and the HOMO-LUMO energy gap of CP-PAHs with a mean absolute error (MAE) of 0.14 eV. The current study also demonstrates that calculations must be carried out for the anion of the corresponding CP-PAH in order to predict LUMO energy of an electron acceptor. Time-dependent CAM-B3LYP with the B3LYP optimized geometry predicts the absorption spectra of CP-PAHs most accurately with a MAE of 29 nm. The results from B3LYP and time-dependent CAM-B3LYP calculations coupled with the new practice in calculating LUMO energy presented in this work show that six of the eight CP-PAHs can accept electrons from the donor material poly(3-hexylthiophene)(P3HT), thus indicating they can be used as electron acceptors of P3HT. Moreover, three pairs of CP-PAHs were identified for their use as highly efficient organic solar cell materials through construction of a P3HT-acceptor1-acceptor2 architecture.

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A computational approach on engineering short spacer for carbazole-based dyes for dye-sensitized solar cells

Cited by 12 publications

References 76 publications

Tuning the HOMO Energy of the Triarylamine Molecules with Orthogonal HOMO and LUMO Using Functional Groups

Tuning the HOMO Energy of the Triarylamine Molecules with Orthogonal HOMO and LUMO Using Functional Groups

DFT studies of proton transfer of 2, 4-dihydroxybenzoic acid derivatives

Electron Acceptability of Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons: Effect of One Electron

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