A new class of triphenylamine-based novel sensitizers for DSSCs: a comparative study of three different anchoring groups

Patil, Dinesh S.; Jadhav, Manoj M.; Avhad, Kiran C.; Islam, Ashraful; Bedja, Idriss; Sekar, Nagaiyan

doi:10.1039/c8nj01029c

Cited by 40 publications

(18 citation statements)

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“…The synthesis of aza‐BODIPY under question is presented in Scheme . The synthesis started with the preparation of the precursor compound, i. e. 1‐(4‐(diphenylamino)phenyl)ethan‐1‐one ( 2 ) . Compound 2 was prepared by a Friedel‐Crafts acylation of triphenylamine ( 1 ) in the presence of zinc chloride as a Lewis acid in 45 % yield.…”

Section: Resultsmentioning

confidence: 99%

“…1‐(4‐(diphenylamino)phenyl)ethan‐1‐one ( 2 ): The described synthesis of 2 is a modification of the procedure reported elsewhere . Acetyl chloride (6.4 g, 5.8 ml, 81.53 mmol) was added dropwise via syringe to a slurry of triphenylamine ( 1 ; 20 g, 81.53 mmol) and ZnCl 2 (11.11 g, 81.53 mmol) in dry dichloromethane (80 ml) at 0 °C.…”

Section: Methodsmentioning

confidence: 99%

“…Furthermore, aza‐BODIPYs were considered as fluorescent chemosensors for the detection of ammonia, cysteine, homocysteine and glutathione in living cells, Hg 2+ , F − , in vivo detection of H 2 S and NO, carbon dioxide, glucose in whole blood and pH‐sensitive sensors . Aza‐BODIPYs have also been tested as photoactive components in photovoltaic devices and nonlinear optical materials …”

Section: Introductionmentioning

confidence: 99%

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Near‐Infrared Photoactive Aza‐BODIPY: Thermally Robust and Photostable Photosensitizer and Efficient Electron Donor

et al. 2020

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We report herein the synthesis of aza-BODIPY substituted with strongly electron-donating p-(diphenylamino)phenyl substituents (p-Ph 2 NÀ ) at 3,5-positions. The presence of p-Ph 2 NÀ groups lowers the energy of the singlet excited state (E s ) to 1.48 eV and induces NIR absorption with λ abs at 789 nm in THF. The compound studied is weakly emissive with the emission band (λ f ) at 837 nm and with the singlet lifetime (τ S ) equal to 100 ps. Nanosecond laser photolysis experiments of the aza-BODIPY in question revealed T 1 !T n absorption spanning from ca. 350-550 nm with the triplet lifetime (τ T ) equal to 21 μs. By introducing a heavy atom (Br) into the structure of the aza-BODIPY, we managed to turn it into a NIR operating photosensitizer. The photosensitized oxygenation of the model compound-diphenylisobenzofuran (DPBF)-proceedes via Type I and/or Type III mechanism without formation of singlet oxygen ( 1 O 2 ). As estimated by CV/DPV measurements, the p-Ph 2 NÀ substituted aza-BODIPYs studied exhibits oxidation processes at relatively low oxidation potentials (E ox 1 ), pointing to the very good electron-donating properties of these molecules. Extremely high photostability and thermal robustness up to approximately 300°C are observed for the p-Ph 2 NÀ substituted aza-BODIPYs. [a] Dr. . Synthesis of mono-bromo aza-BODIPY 7. Reaction conditions: a) acetyl chloride, ZnCl 2 , DCM, 0°C to reflux, 24 h, 45 %; b) 4-tert-butylbenzaldehyde, NaOH, EtOH, 0°C to RT, 24 h, 69 %; c) MeNO 2 , K 2 CO 3 , MeOH, reflux, 17 h, 79 % ; d) CH 3 COONH 4 ,n-butanol, 117°C, 3 h, 63 %; e) BF 3 · Et 2 O, DIPA, DCM, 1 h, 91 %; f) NBS, DCM, 2 h, 0°C, 96 %.ChemPhysChem Articles

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Near‐Infrared Photoactive Aza‐BODIPY: Thermally Robust and Photostable Photosensitizer and Efficient Electron Donor

et al. 2020

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“…LUMOs of the molecule was populated at acceptor salicylic acid unit Figure 4. This signifies the ICT between donor carbazole and acceptor unit in the dye [24], [57(c-d)], [61]. The energy gap between HOMO and LUMO were calculated and are shown in Figure 5.…”

Section: Dft Studymentioning

confidence: 99%

“…Metal-free dyes consist of D-π-A systems linked via a π-delocalized spacer. [17] A wide number of groups such as coumarins, [18] merocyanines, [19] cyanines, [20] indolines, [18] hemicyanines, [21] triphenylamines are used as a photodyes [18][19][20][21][22][23][24][25][26][27][28] in DSSC.…”

Section: Introductionmentioning

confidence: 99%

Multi‐Dentate Carbazole Based Schiff Base Dyes with Chlorovinylene Group in Spacer for Dye‐Sensitized Solar Cells: A Combined Theoretical and Experimental Study.

et al. 2019

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Four new metal free organic Schiff bases employing N-hexyl/Nphenyl carbazole moiety as a donor, 1-chlorobuta-1,3-diene as a π-bridge and 4-amino salicylic acid as an anchor, are designed, synthesized and investigated as photosensitizers in the dye-sensitized solar cell (DSSC). We have studied the combined effect of the introduction of electronegative chlorine group with an additional double bond in π-conjugation and 4amino salicylic acid as a tridentate anchoring group, on the optoelectronic, theoretical and photovoltaic performance of the dyes. The halogen electronegativity and strong polarization of the C-X bond represented interesting acceptor moieties for organic push-pull systems. The designed strategy leads to redshifted absorption maxima and reduced band gap. Density functional theory (DFT) and Time dependent density functional theory (TD-DFT) are used to support the performance of the obtained carbazole based Schiff-base dyes. When compared with the other three dyes, 3b exhibited the smallest band gap (2.86 eV), red-shifted absorption spectra on TiO 2 surface (453 nm) and improved nonlinear optical (NLO) properties. Among the four reported dyes, 3b exhibited the excellent photovoltaic performance, short-circuit current density (J sc ) of 10.60 mA/cm 2 , open-circuit voltage (V oc ) of 0.626 V and fill factor (FF) of 70.0 %, conforming to a total power conversion efficiency of 4.3% under 1 sun light illumination due to the presence of two anchoring groups with multiple binding sites on TiO 2 surface leading to efficient charge injection. NLO properties are examined theoretically and dye 3b exhibited the highest value of the first hyperpolarizability (β) amongst all four dyes which are in good agreement with exhibited highest DSSC efficiency. The present work revealed that the incorporation of electronegative chlorine group in π-conjugation and the use of double acceptors with multiple binding sites for better adsorption on TiO 2 surface are crucial to supplement the efficiency of the dye.

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Recent developments in metal‐free organic sensitizers derived from carbazole, triphenylamine, and phenothiazine for dye‐sensitized solar cells

et al. 2021

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Summary In the present context of increasing population, renewable and sustainable energy alternatives are very much essential to satisfy the necessities of the world. To satisfy this growing demand, scientists are prioritizing the production of cost‐effective and high‐performance clean energy appliances. Dye‐sensitized solar cells (DSSCs) are one such material that is at the forefront of modern solar cell technologies. Being one of the main components of DSSCs, metal‐free organic dyes play a crucial role in light processing and electron injection. In recent times, carbazole (CZ)‐, triphenylamine (TPA)‐, and phenothiazine (PTZ)‐based derivatives have been identified as suitable alternatives to Ru(II) polypyridyl complexes because they are easy to synthesize and exhibit excellent thermal and electronic properties. This review focuses largely on the latest developments in the use of monoanchored and multianchored CZ, TPA, and PTZ scaffolds for DSSC applications and focuses especially on the correlation between molecular design and photovoltaic performance. The physical properties of devices can be adjusted through the sensitizer's strategic design that helps to improve the performance of the devices. We tabulated the photovoltaic parameters corresponding to all dyes presented in this review. Also, applications of additives are presented after the systematic review on CZ‐, TPA‐, and PTZ‐based dyes.

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A new class of triphenylamine-based novel sensitizers for DSSCs: a comparative study of three different anchoring groups

Abstract: Triphenylamine-based dyes with chloro groups suitably placed on their π-linkers affect DSSC efficiency.

Cited by 40 publications

References 83 publications

Near‐Infrared Photoactive Aza‐BODIPY: Thermally Robust and Photostable Photosensitizer and Efficient Electron Donor

Near‐Infrared Photoactive Aza‐BODIPY: Thermally Robust and Photostable Photosensitizer and Efficient Electron Donor

Multi‐Dentate Carbazole Based Schiff Base Dyes with Chlorovinylene Group in Spacer for Dye‐Sensitized Solar Cells: A Combined Theoretical and Experimental Study.

Recent developments in metal‐free organic sensitizers derived from carbazole, triphenylamine, and phenothiazine for dye‐sensitized solar cells

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