Branched Methoxydiphenylamine-Substituted Carbazole Derivatives for Efficient Perovskite Solar Cells: Bigger Is Not Always Better

Luizys, Povilas; Xia, Jianxing; Daškevičienė, Marytė; Kantminienė, Kristina; Kasparavičius, Ernestas; Kanda, Hiroyuki; Zhang, Yi; Jankauskas, Vygintas; Rakštys, Kasparas; Getautis, Vytautas; Nazeeruddin, Mohammad Khaja

doi:10.1021/acs.chemmater.1c02114

Cited by 13 publications

(4 citation statements)

References 79 publications

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“…The synthesized molecules consist of unconjugated flexible linker and four peripheral diphenylamine groups with methoxy groups at different positions (pp-, pm-, and po-). The synthetic route involves nucleophilic substitution of 3,6-diiodo-9 H -carbazole and 1,4-dibromobutane followed by palladium-catalyzed C–N cross-coupling reaction with dimethoxy diphenylamine isomers, whereas, in 2021, Luizys et al synthesized a compound based on carbazole derivatives bearing 3,6-bis(4,4′- dimethoxydiphenylamino)carbazole in the peripheral linked together by aliphatic chains termed as Cz-OMeDPA, 2Cz-OMeDPA (Figure ), 2Cz-OMeDPA-OH, 3Cz-OMeDPA, 3Cz-OMeDPA-OH, 4Cz-OMeDPA, and 4CzOMeDPA-OH . Here the twin carbazole based HTMs are synthesized; the reason from simple to twin carbazole based HTMs is because the poor intramolecular charge transport can be overcome through developing intermolecular interaction in bulk material which in turn enhances the charge transport properties by potential intermolecular interaction.…”

Section: Carbazole-based Htmsmentioning

confidence: 99%

Review on Carbazole-Based Hole Transporting Materials for Perovskite Solar Cell

Radhakrishna

Manjunath

Devadiga

et al. 2023

ACS Appl. Energy Mater.

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Solar cells constructed with organic−inorganic metal halide perovskite is a hot topic as they can replace the existing traditional silicon-based solar cells. The major hurdle in the commercialization of perovskite solar cells is the efficiency of the device. In this context, the use of a suitable organic hole transporting material would improve the efficiency of the perovskite solar cells. Until now, spiro-OMeTAD (2,2′,7,7′-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9′-spirobifluorene) is the standard hole transporting material (HTM) used in the fabrication of perovskite solar cells, and the major issue associated with spiro-OMeTAD is the complex multistep synthesis and the observed difficulty in the purification steps which make this HTM as cost-ineffective. Nowadays, certain hole transporting materials made up of organic small molecules carrying motifs like thiophene, triphenylamine, triazatruxane, pyrene, and carbazole exhibited better photovoltaic properties and less costs are involved for their synthesis, which motivate the researchers to work further on the design and development of non-spiro-OMeTAD. Among the various organic small molecule based HTMs, carbazole unit based HTMs exhibited better photovoltaic properties, chemical stability, easy functionalization, and device performance. Thus, the present review mainly focused on the diverse carbazole-based hole transporting molecular designs and their synthetic strategies which have been reported during the past eight years. Also, the review tries to correlate the molecular structure of different carbazole-based HTMs and their observed energy band gap, HOMO−LUMO levels, hole mobilities, and power conversion efficiencies for the fabricated perovskite solar cells.

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Section: Carbazole-based Htmsmentioning

confidence: 99%

Review on Carbazole-Based Hole Transporting Materials for Perovskite Solar Cell

Radhakrishna

Manjunath

Devadiga

et al. 2023

ACS Appl. Energy Mater.

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“…Furthermore, donor (arylamine) π spacer-donor (arylamine) materials have been designed to synthesize novel HTMs by straightforward modifications. Thiophene compounds, , fluorene-thiophene, and carbazole compounds, , bound by donors (amine groups), are extensively explored in PSCs to substitute the costly and unstable Spiro-OMeTAD. From all these compounds, anthracene-based compounds stand out for their promising features and widespread use in these devices, such as organic transistors with thin films, light-producing diodes, and perovskite-type OSCs. – Using easily synthesized anthracene HTMs, Liu recently achieved a PEC of 17.27% .…”

Section: Introductionmentioning

confidence: 99%

Molecular Engineering of Anthracene Core-Based Hole-Transporting Materials for Organic and Perovskite Photovoltaics

Shafiq,

Adnan,

Hussain

et al. 2023

ACS Omega

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Anthracene core-based hole-transporting material containing TIPs (triisopropylsilylacetylene) has been spotlighted as potential donors for perovskite solar cells (SCs) due to their appropriate energy levels, efficient hole transport capacity, high stability, and high power conversion efficiency. Herein, we have efficiently designed seven new highly conjugated A−B−D−C−D molecules (AS1−AS7) containing an anthracene core. We used end-capped modifications of donor units with acceptor units on one side and then theoretically characterized them for their appropriate use for SC applications. Modern quantum chemistry techniques have theoretically described the R (reference molecule) and developed (AS1−AS7) molecules. Moreover, the proposed (AS1−AS7) molecules are explored with density functional theory (DFT) and time-dependent density functional theory (TD-DFT) employing B3LYP/6-31G(d,p), and numerous parameters like photovoltaic, optical and electronic characteristics, frontier molecular orbital, excitation, binding and reorganization (λ e and λ h ) energies, open circuit voltage, light harvesting efficiency, transition density matrix, fill factor, and the density of states have been studied. End-capped modification causes a smaller band gap between the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO), higher UV−vis absorption maxima, tuned energy levels, lower binding and reorganizational (λ e and λ h ) energies, and larger V oc values in proposed (AS1−AS7) molecules than R. AS5 has a remarkable absorption maximum of 495.94 nm and a narrow optimal energy gap (E g ) of 1.46 eV. Furthermore, a complex study of AS5:PC61BM has revealed extraordinary charge shifting at the HOMO (AS5)−LUMO (PC 61 BM) interface. Our results suggested that newly developed anthracene core-based compounds (AS1− AS7) would be effective candidates with excellent photovoltaic and optoelectronic properties and could be employed in future organic and perovskite SC applications.

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“…The chosen donor moiety is 3,6-bis(4,4 -dimethoxydiphenylamino)carbazole (3, [30]. 3,6-CzDMPA-based HTMs have attracted much attention due to their interesting physicochemical properties, such as molecular glass behavior, excellent thermal stability and good solubility, and good charge transport properties [31,32]. We have extensively studied this class of HTMs in dye-sensitized solar cells (DSSCs) and PSC applications [11,[33][34][35][36][37][38].…”

Section: Introductionmentioning

confidence: 99%

D-π-A-Type Pyrazolo[1,5-a]pyrimidine-Based Hole-Transporting Materials for Perovskite Solar Cells: Effect of the Functionalization Position

et al. 2022

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Donor–acceptor (D–A) small molecules are regarded as promising hole-transporting materials for perovskite solar cells (PSCs) due to their tunable optoelectronic properties. This paper reports the design, synthesis and characterization of three novel isomeric D-π-A small molecules PY1, PY2 and PY3. The chemical structures of the molecules consist of a pyrazolo[1,5-a]pyrimidine acceptor core functionalized with one 3,6-bis(4,4′-dimethoxydiphenylamino)carbazole (3,6-CzDMPA) donor moiety via a phenyl π-spacer at the 3, 5 and 7 positions, respectively. The isolated compounds possess suitable energy levels, sufficient thermal stability (Td > 400 °C), molecular glass behavior with Tg values in the range of 127–136 °C slightly higher than that of the reference material Spiro-OMeTAD (126 °C) and acceptable hydrophobicity. Undoped PY1 demonstrates the highest hole mobility (3 × 10−6 cm2 V−1 s−1) compared to PY2 and PY3 (1.3 × 10−6 cm2 V−1 s−1). The whole isomers were incorporated as doped HTMs in planar n-i-p PSCs based on double cation perovskite FA0.85Cs0.15Pb(I0.85Br0.15)3. The non-optimized device fabricated using PY1 exhibited a power conversion efficiency (PCE) of 12.41%, similar to that obtained using the reference, Spiro-OMeTAD, which demonstrated a maximum PCE of 12.58% under the same conditions. The PY2 and PY3 materials demonstrated slightly lower performance in device configuration, with relatively moderate PCEs of 10.21% and 10.82%, respectively, and slight hysteresis behavior (−0.01 and 0.02). The preliminary stability testing of PSCs is also described. The PY1-based device exhibited better stability than the device using Spiro-OMeTAD, which could be related to its slightly superior hydrophobic character preventing water diffusion into the perovskite layer.

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Branched Methoxydiphenylamine-Substituted Carbazole Derivatives for Efficient Perovskite Solar Cells: Bigger Is Not Always Better

Cited by 13 publications

References 79 publications

Review on Carbazole-Based Hole Transporting Materials for Perovskite Solar Cell

Review on Carbazole-Based Hole Transporting Materials for Perovskite Solar Cell

Molecular Engineering of Anthracene Core-Based Hole-Transporting Materials for Organic and Perovskite Photovoltaics

D-π-A-Type Pyrazolo[1,5-a]pyrimidine-Based Hole-Transporting Materials for Perovskite Solar Cells: Effect of the Functionalization Position

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