Rational modifications on champion porphyrin dye SM315 using different electron-withdrawing moieties toward high performance dye-sensitized solar cells

Ji, Zhang; Zhang, Jian-Zhao; Li, Haibin; Wu, Yong; Geng, Yun; Su, Zhong‐Min

doi:10.1039/c4cp03355h

Cited by 45 publications

(27 citation statements)

References 84 publications

(94 reference statements)

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“…However, to the best of our knowledge, TPz has only been examined in DSC dyes with both donor and acceptor groups substituted on the thiophene a single time potentially due to a synthetically challenging desymmeterization, which is needed to give directional electron flow across the molecule . Encouragingly, several computational reports are available with donor–acceptor substituted TPz bridges at the thiophene positions with interesting predicted properties such as increased absorption intensity, increased absorption breadth, and high tunability of dye energy levels. − Only the donor–acceptor structural arrangement utilizes the proaromatic nature of the pyrazine ring for maximum light absorption according to valence bond theory.…”

Section: Introductionmentioning

confidence: 99%

Thieno[3,4-b]pyrazine as an Electron Deficient π-Bridge in D–A−π–A DSCs

Liyanage

Yella

Nazeeruddin

et al. 2016

ACS Appl. Mater. Interfaces

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Thieno[3,4-b]pyrazine (TPz) is examined as an electron deficient π-bridge enabling near-infrared (NIR) spectral access in dye-sensitized solar cells (DSCs). Seven dissymmetric dyes for DSCs were synthesized (NL2-NL8) with TPz as the π-bridge utilizing palladium catalyzed C-H activation methodology. C-H bond cross-coupling was uniquely effective among the cross-couplings and electrophilic aromatic substitution reactions analyzed in monofunctionalizing the TPz building block. The TPz-based NL2-NL8 dyes examine the effects of various donors, π-spacers, and acceptors within the donor-π bridge-acceptor (D-π-A) dye design. Proaromatic TPz stabilizes the excited-state oxidation potential (E(s+/s*)) of the dyes by maintaining aromaticity upon excitation of the dye molecule. This leads to concise conjugated systems capable of accessing the NIR region. Through judicious structural modifications, dye band gaps were reduced to 1.48 eV, and power conversion efficiencies (PCEs) reached 7.1% in this first generation TPz-dye series.

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Section: Introductionmentioning

confidence: 99%

Thieno[3,4-b]pyrazine as an Electron Deficient π-Bridge in D–A−π–A DSCs

Liyanage

Yella

Nazeeruddin

et al. 2016

ACS Appl. Mater. Interfaces

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“…When charge separation distance is not enough to overcome the electrostatic attraction between electrons and holes and charge recombination occurs . The rate of charge recombination decreases with increasing distances between dye cation holes and TiO 2 surfaces (R) . As shown in Figure , the R decrease in the order of D3‐L4 (13.95 Å) > D3‐L3 (13.66 Å) > D3‐L2 (11.02 Å) > D3‐L1 (10.62 Å) > D3 (7.15 Å).…”

Section: Resultsmentioning

confidence: 85%

Push‐Pull N‐Annulated Perylene‐Based Sensitizers for Dye‐Sensitized Solar Cells: Theoretical Property Tuning by DFT/TDDFT

Hadsadee

Rattanawan

Tarsang³

et al. 2017

ChemistrySelect

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We evaluate the effects of donor and π‐linker moieties on power‐conversion efficiency for a series of push‐pull type, N‐annulated perylene dyes for dye‐sensitized solar cells. Triphenylamine and diphenylamine are used as electron donors. We investigate the structural, optical, and electronic properties of dyes by performing density functional theory (DFT) calculations at the B3LYP level, using the 6‐311G(d,p) basis set. Electronic absorption wavelengths were investigated using time dependent DFT (TD‐DFT) calculations on M062x/6‐311G(d,p) in THF. Our calculated results reveal that the diphenylamine (DPA) donor provides a small dihedral angle between diphenylamine and the perylene core, resulting in a red‐shifted absorption spectrum. Introduction of an O‐methoxy substituent into diphenylamine improves its donor properties, red‐shifts the absorption wavelength, and increases the dipole moment, indicating increased intramolecular charge transfer in the O‐methoxy substituted dye. Incorporation of a C‐C triple bond in linker extends the π‐conjugation system and decreases the dihedral angle between N‐annulated perylene and cyanoacrylic acid; the dye adopts a planar structure, causing a red‐shift in the absorption spectrum. Our results demonstrate that use of computational design can to help the experimentalist for out looking future developments to identify push‐pull perylene sensitizers for highly efficient solar cells.

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“…Here we want to bring it to readers notice that recent reports have shown that the Electron Withdrawing Groups (EWG), NTz of structure 39 containing two fused 1, 2, 5‐thiadiazole rings lower the band gap, enhance the inter‐chain packing and also improve the charge mobility in polymer studies . Besides Zhang et al in their computational study has recently predicted structure 39 as a promising candidate for DSC. However replacement of BTD with dithieno 3, 2‐b: 2′, 3′‐d pyrrole (in structure 35 and 36) has significantly lowered the potential of LUMO.…”

Section: Resultsmentioning

confidence: 93%

Molecular design of porphyrin dyes for dye sensitized solar cells: A quantitative structure property relationship study

Madugula

Soujanya

2017

Int J Quantum Chem

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Porphyrins dyes are known as promising sensitizers for dye sensitized solar cell (DSC) devices because of their intrinsic features with maximum reported light-to-electricity conversion efficiency of about 12%. Our objective in this study is to rationally design new porphyin sensitizers with enhanced photovoltaic (PV) properties, V oc (open-circuit voltage), or J sc (short-circuit current density) for DSC applications. We have used quantitative structure-property relationship technique following a heuristic approach to build a structure-property (PV) relationship on a dataset of 45 experimentally reported push-pull Zn-porphyrin based sensitizers. The model is further used to predict PV properties; V oc and J sc of 71 new structures. The model includes a unique combination of constitutional, topological, and electrostatic descriptors along with the widely used quantum chemical descriptors to establish a structure-property relationship. The results furnished guide-in principles in identifying 8 structures as potential candidates based on their frontier molecular orbital energies, absorption in visible-near IR region (extending up to 900 nm), reorganization energies, in addition to favorable PV properties. In conclusion, the study has demonstrated how a subtle variation in porphyrin structure particularly of the auxiliary groups can be used to modulate their PV properties. K E Y W O R D S descriptors, dye sensitized solar cell, Porphyrin sensitizers, quantitative structure-property relationship, Voc and Jsc Int J Quantum Chem. 2017;117:e25385.

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Rational modifications on champion porphyrin dye SM315 using different electron-withdrawing moieties toward high performance dye-sensitized solar cells

Cited by 45 publications

References 84 publications

Thieno[3,4-b]pyrazine as an Electron Deficient π-Bridge in D–A−π–A DSCs

Thieno[3,4-b]pyrazine as an Electron Deficient π-Bridge in D–A−π–A DSCs

Push‐Pull N‐Annulated Perylene‐Based Sensitizers for Dye‐Sensitized Solar Cells: Theoretical Property Tuning by DFT/TDDFT

Molecular design of porphyrin dyes for dye sensitized solar cells: A quantitative structure property relationship study

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