Synthesis and characterization of simple cost-effective trans-A<sub>2</sub>BC porphyrins with various donor groups for dye-sensitized solar cells

Kumar, Ravi; Sankar, Muniappan; Sudhakar, Vediappan; Krishnamoorthy, Kothandam

doi:10.1039/c5nj02610e

Cited by 14 publications

(22 citation statements)

References 79 publications

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“…First, the PCEs of these porphyrin systems are indeed much lower than those of the champion push-pull porphyrin sensitizers, which reach PCEs around 13-14%. 71,72 Compared with previously reported similar simple tetraryl zinc porphyrins, 73 the dyes of this study display lower PCEs essentially due to their lower Jsc, although one publication from Diau and coworkers 74 reports similar performances as ours. It is likely that the electron withdrawing substituent (amide or ester) in trans position to the anchoring moiety modifies the electron distribution in the excited state that disfavors electron injection efficiency.…”

Section: Photovoltaic Performances In Dye Sensitized Solar Cellssupporting

confidence: 56%

Dye-Sensitized Photoelectrosynthesis Cells for Benzyl Alcohol Oxidation Using a Zinc Porphyrin Sensitizer and TEMPO Catalyst

et al. 2021

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based DSPEC using a zinc porphyrin (ZnP) sensitizer and a TEMPO organo-catalyst that quite efficiently catalyzes light driven oxidation of methoxybenzyl alcohol into aldehyde. Two dyads ZnP-TEMPO, differing by the anchoring group (carboxylic acid and hydroxamic acid) on ZnP, were prepared and their electrochemical, absorption, emission properties were recorded and quantum chemical modelling was realized. The photovoltaic performances in DSSCs were first examined in order to optimize the dyeing conditions and compare the relative efficiencies of the compounds. The dyads substituted with TEMPO outperform the reference zinc porphyrin lacking TEMPO with a much higher Jsc and Voc. The photocatalytic properties after immobilization on TiO 2 nanocrystalline films towards para-methoxy benzyl alcohol oxidation were explored in borate buffer and in acetonitrile electrolyte. In borate buffer, the optimal pH was 8 and using the dyad ZnP-TEMPO anchored with hydroxamic acid, para-methoxy benzaldehyde was selectively produced with average photocurrent density of 200 A/cm 2 , a faradaic efficiency of 82%, a TON of 26, and a TOF of 47 h -1 . In acetonitrile in presence of 0.1 M of N-methyl-imidazole, the same dyad gives an average photocurrent density of about 100 A/cm 2 , a faradaic efficiency of 76%, a TON of 13, and a TOF of 24 h -1 . The stability of the anchor is crucial in acetonitrile electrolyte, where the dyad is quite soluble, since only the dyad functionalized with hydroxamic acid is compatible with these organic solvent conditions. Overall this study paves the way to the development of more efficient and probably more stable TiO 2 based DSPECs for alcohol oxidation that could advantageously complement those devoted to water oxidation.

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Section: Photovoltaic Performances In Dye Sensitized Solar Cellssupporting

confidence: 56%

Dye-Sensitized Photoelectrosynthesis Cells for Benzyl Alcohol Oxidation Using a Zinc Porphyrin Sensitizer and TEMPO Catalyst

et al. 2021

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“…[22] Indoline substituted porphyrin dyes are reported to yield PCE conversion efficiency upto 10 %. [20,32,33] Recently, a new set of push-pull zinc porphyrin sensitizers revealed an impressive PCE of 13-14 %. This brings out the significance of structural modification of the dyes to alleviate dye aggregation.…”

Section: Introductionmentioning

confidence: 99%

“…This brings out the significance of structural modification of the dyes to alleviate dye aggregation. [20,32,33] Recently, a new set of push-pull zinc porphyrin sensitizers revealed an impressive PCE of 13-14 %. [34] From all these observations it is clear that high PCE for porphyrin dyes could be achieved by (i) peripheral modification of the porphyrin structure for wide-band absorption and tuning of energy levels, (ii) enhanced push-pull effects from donor moiety to acceptor moiety within the sensitizer, and (iii) the choice of bridge (linker) connecting the porphyrin to the semiconductor surface.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectral, Electrochemical and Photovoltaic Studies of A₃B Porphyrinic Dyes having Peripheral Donors

et al. 2019

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Three new 'push-pull' A 3 B Zn(II)porphyrin dyes having mesopyrenyl, carbazolyl and phenothiazine as electron donors (A) and phenylcarboxylic acid as acceptor/anchor (B) were synthesized and utilized for DSSC application. The spectral and electrochemical redox properties of these new dyes were studied and compared with trans-A 2 BC Zn(II) porphyrin dyes under similar experimental conditions. Red-shifted, broadened absorption peaks, lower fluorescence quantum yields, and shortened lifetimes were observed for the A 3 B dyes as compared to zinc tetraphenylporphyrin control, ZnTPP. DFT optimized structures suggested effective charge separation related to enhanced charge injection efficiency. Driving force for electron injection (ΔG inj ) and dye regeneration (ΔG reg ) calculated from the spectral and electrochemical studies predicted facile electron injection from excited dye into semiconductor TiO 2 in the constructed solar cells. Phenothiazine appended dye (KP-TriPTZ-Zn) showed the highest η value of 7.3 % for PCE with greater J sc and V oc values due to its better light harvesting ability and reduced dye aggregation as compared to other dyes. Our studies demonstrate that the dyes having multiple electron-donating groups exhibit higher photon-to-current conversion efficiency.[a] Dr.

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“…Krishnamoorthy et al. reported mono pyrenyl attached porphyrin which has absorption at 423 nm . Due to attachment of tetrafluoro phenyl group in 4 g the core of the porphyrin becomes electron deficient and shows a blue‐shifted absorption at 422 nm.…”

Section: Resultsmentioning

confidence: 99%

“…The utilization of suitably functionalized trans ‐A 2 B 2 porphyrin building blocks in the construction of novel types of metal‐organic‐frameworks is currently in progress. Targeted syntheses of differently meso‐ substituted porphyrins of types A 3 B, 5,10‐A 2 B 2 , trans ‐A 2 BC and ABCD, with a wide variety of substituents are well documented in the literature.…”

Section: Discussionmentioning

confidence: 99%

Scalable Synthesis and Supramolecular Assembly of trans‐A₂B₂ Porphyrins with Pendant Carboxylic Functional Groups

2017

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This article deals with facile synthesis of A2B2 porphyrins bearing carboxylate groups at 5,15‐ positions and different functional groups at 10,20‐ positions viz. 4‐iodophenyl (a), 4‐tert‐butylphenyl (b), 3,5‐dimethoxyphenyl (c) 3‐carboxyphenyl (d), 2‐thienyl (e) 4‐nitrophenyl (f), 4‐methoxy‐2,3,5,6‐tetrafluorophenyl (g) and 2‐pyrenyl (h) as single major component in scalable yields. It relates also to the supramolecular assembly modes of these species. The use of stoichiometric amounts of trifluoroacetic acid in condensation of 5‐(4‐methoxycarbonylphenyl)dipyrromethane and different aldehydes led to the formation of trans‐porphyrins as di‐esters (1 a‐1 h). These were transformed by hydrolysis to the corresponding di‐acids (2 a‐2 h). (1 a‐1 h) and (2 a‐2 h) were then core‐metalated to afford the corresponding metalloporphyrin species (3 a‐3 h) and (4 a‐4 h). The absorption and emission spectra of the free base (2 a‐2 h) and metallated porphyrins (4 a‐4 h) were found greatly influenced by the substituents at 10,20‐positions. SEM studies of solids deposited on surfaces from solution exhibited hydrogen‐bonded block‐shaped structures of 2 e and fibrous sheets of 2 f. Co‐crystallization of 2 a and 2 g with 4,4′‐bipyridyl yielded hetero‐molecular structures stabilized by both hydrogen O−H⋅⋅⋅N, and halogen N⋅⋅⋅I bonds in 2 a, and by O−H⋅⋅⋅N hydrogen bonds and C−F⋅⋅⋅π interactions in 2 g.

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Synthesis and characterization of simple cost-effective trans-A₂BC porphyrins with various donor groups for dye-sensitized solar cells

Abstract: Zn(ii) porphyrin dyes have been synthesized in three steps and exhibited power conversion efficiencies of 2.1 to 4.2% which depend on the electron donating ability of the R group.

Cited by 14 publications

References 79 publications

Dye-Sensitized Photoelectrosynthesis Cells for Benzyl Alcohol Oxidation Using a Zinc Porphyrin Sensitizer and TEMPO Catalyst

Dye-Sensitized Photoelectrosynthesis Cells for Benzyl Alcohol Oxidation Using a Zinc Porphyrin Sensitizer and TEMPO Catalyst

Synthesis, Spectral, Electrochemical and Photovoltaic Studies of A₃B Porphyrinic Dyes having Peripheral Donors

Scalable Synthesis and Supramolecular Assembly of trans‐A₂B₂ Porphyrins with Pendant Carboxylic Functional Groups

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Synthesis and characterization of simple cost-effective trans-A2BC porphyrins with various donor groups for dye-sensitized solar cells

Abstract: Zn(ii) porphyrin dyes have been synthesized in three steps and exhibited power conversion efficiencies of 2.1 to 4.2% which depend on the electron donating ability of the R group.

Cited by 14 publications

References 79 publications

Dye-Sensitized Photoelectrosynthesis Cells for Benzyl Alcohol Oxidation Using a Zinc Porphyrin Sensitizer and TEMPO Catalyst

Dye-Sensitized Photoelectrosynthesis Cells for Benzyl Alcohol Oxidation Using a Zinc Porphyrin Sensitizer and TEMPO Catalyst

Synthesis, Spectral, Electrochemical and Photovoltaic Studies of A3B Porphyrinic Dyes having Peripheral Donors

Scalable Synthesis and Supramolecular Assembly of trans‐A2B2 Porphyrins with Pendant Carboxylic Functional Groups

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Synthesis and characterization of simple cost-effective trans-A₂BC porphyrins with various donor groups for dye-sensitized solar cells

Synthesis, Spectral, Electrochemical and Photovoltaic Studies of A₃B Porphyrinic Dyes having Peripheral Donors

Scalable Synthesis and Supramolecular Assembly of trans‐A₂B₂ Porphyrins with Pendant Carboxylic Functional Groups