The electronic structures and charge transfer properties of tetra(naphthalene-dione)porphyrins and tetra(naphthalene-dithione)porphyrins as dye-sensitized solar cell skeleton

Qi, Dongdong; Jiang, Jianzhuang

doi:10.1002/qua.24517

Cited by 9 publications

(11 citation statements)

References 40 publications

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“…Recent computational studies point to the special role of the four naphthoquinone functions fused to the b,b'-positions in modifying the conjugated p-systemo f the porphyrin core. [29] This theoretical result encourages the searchf or more experiment-based insights into blackened porphyrins. However,furthertheoretical work might also enlighten the special structural basis for the unusual properties of the b,b'-naphthoquinone-modified porphyrins.…”

Section: Crystal Structures Of Ni-porphyrinsmentioning

confidence: 76%

“…With the two tetra‐naphthoquinonoporphyrins 6–Ni and 6‐2H , in particular, first analogues of the blackened porphyrin 6–Zn were created. Recent computational studies point to the special role of the four naphthoquinone functions fused to the β,β′‐positions in modifying the conjugated π‐system of the porphyrin core . This theoretical result encourages the search for more experiment‐based insights into blackened porphyrins.…”

Section: Resultsmentioning

confidence: 94%

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Panchromatic π‐Extended Porphyrins from Conjugation with Quinones

2016

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Typical porphyrins are coloured compounds due to their characteristic wavelength‐selective visible light absorptions. An exceptional “blackened” ZnII–porphyrin was recently obtained from fusing the β,β′‐positions of the porphyrin core with four quinone units. Here, studies with metal‐free and NiII‐containing analogues are reported. These quinone‐fused porphyrins were prepared from the corresponding β,β′‐tetrasulfolenoporphyrins via thermally generated porphyrindienes, which were trapped by [4+2] cycloaddition as benzoquinone cycloadducts, which were subsequently oxidised. By using this strategy, metal‐free and NiII‐containing porphyrins with one, two, three or four conjugated naphthoquinone moieties were prepared efficiently. The presence of the π‐conjugated naphthoquinone moieties changed the porphyrin chromophores profoundly, giving broadly absorbing “blackened” pigments. The influence of coordinated NiII ions, or of the absence of a metal ion in the modified porphyrin core, on their structural and spectroscopic properties was explored. Blackened quinone‐conjugated porphyrins might be pigments suitable for solar energy conversion. With their unique peripheral functional groups they are also a set of porphyrins “programmed” for further covalent extension. Thus, they are building blocks for the preparation of supra‐porphyrinoid assemblies that might be useful in optoelectronics and in the nanosciences.

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Section: Crystal Structures Of Ni-porphyrinsmentioning

confidence: 76%

Section: Resultsmentioning

confidence: 94%

Panchromatic π‐Extended Porphyrins from Conjugation with Quinones

2016

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“…The light‐harvesting efficiency (LHE) has been computed according to LHE = 1 − 10 − f , where f is the oscillator strength of the dye related to the λ max . This parameter can be interpreted as the light absorbance of the dye‐sensitized TiO 2 film and should be higher as possible to maximize the photocurrent response . Finally, the driving force for charge recombination (

Δ G_{rec}^{0}

) has been calculated according to

Δ G_{rec}^{0}

= E CB –

E_{HOMO .}

…”

Section: Methodsmentioning

confidence: 99%

Exploring the relevance of thiophene rings as bridge unit in acceptor‐bridge‐donor dyes on self‐aggregation and performance in DSSCs

et al. 2017

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The possibility of dye charge recombination in DSSCs remains a challenge for the field. This consists of: (a) back-transfer from the TiO to the oxidized dye and (b) intermolecular electron transfer between dyes. The latter is attributed to dye aggregation due to dimeric conformations. This leads to poor electron injection which decreases the photocurrent conversion efficiency. Most organic sensitizers are characterized by an Acceptor-Bridge-Donor (A-Bridge-D) arrangement that is commonly employed to provide charge separation and, therefore, lowering the unwanted back-transfer. Here, we address the intermolecular electron transfer by studying the dimerization and photovoltaic performance of a group of A-Bridge-D structured dyes. Specifically, eight famous sulfur containing π-bridges were analyzed (A and D remained fixed). Through quantum mechanical and molecular dynamics approaches, it was found that the formation of weakly stabilized dimers is allowed. The dyes with covalently bonded and fused thiophene rings as Bridges, 6d and 7d as well as 8d with a fluorene, would present high aggregation and, therefore, high probability of recombination processes. Conversely, using TiO cluster and surface models, delineated the shortest bridges to improve the adsorption energy and the stability of the system. Finally, the elongation of the bridge up to 2 and 3 units and their photovoltaic parameters were studied. These results showed that all the sensitizers are able to provide similar photocurrent outcomes, regardless of whether the bridge is elongated. © 2017 Wiley Periodicals, Inc.

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“…(3.8). The Voc value is directly determined by shift in the conduction band edge of the semiconductor (ΔECB) [34][35][36]. Based on the computational data, it could be inferred that larger Voc value could be obtained with the SP-OO dye over other dyes owing to its slower charge recombination property and larger ΔECB.…”

Section: Open-circuit Voltage Analysismentioning

confidence: 99%

Triphenylamine Based Organic Dyes with Different Spacers for Dye-Sensitized Solar Cells: A First Principle Study

Prakasam¹,

Baskar²,

Gnanamoorthi³

et al. 2019

IJASE

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The four novel metal-free organic dyes Ref. Dye, SP-SO, SP-OS and SP-OO, containing a Triphenylamine (TPA) unit as the π-bridge were designed and the impacts of the spacer on the photovoltaic performances were studied. The Geometry structure, energy levels, light-harvesting ability and ultraviolet-visible absorption spectra were calculated by using Density Functional Theory (DFT) and Time-Dependent-DFT. The results show that incorporating spacer with moderate electron-deficient ability can extend the absorption range (400-950 nm) and adjust the molecular orbital energy levels, improving the photovoltaic performance devices. The investigated dye reveals that SP-SO sensitizers showed absorbance in the visible region (400-950 nm) with higher oscillator strength (f) (1.1178and LHE (0.9237).

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The electronic structures and charge transfer properties of tetra(naphthalene-dione)porphyrins and tetra(naphthalene-dithione)porphyrins as dye-sensitized solar cell skeleton

Cited by 9 publications

References 40 publications

Panchromatic π‐Extended Porphyrins from Conjugation with Quinones

Panchromatic π‐Extended Porphyrins from Conjugation with Quinones

Exploring the relevance of thiophene rings as bridge unit in acceptor‐bridge‐donor dyes on self‐aggregation and performance in DSSCs

Triphenylamine Based Organic Dyes with Different Spacers for Dye-Sensitized Solar Cells: A First Principle Study

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