Effect of structural modification on the performances of phenothiazine-dye sensitized solar cells

Liu, Xuxu; Long, Jun; Guo, Wei; Pei, Yong; Zhao, Bin; Tan, Songting

doi:10.1016/j.dyepig.2015.05.012

Cited by 39 publications

(17 citation statements)

References 58 publications

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“…There was absorbance of PTZTID solutions at λ max 518 nm over the concentration range 1 × 10 −5 M to 2 × 10 −4 M, but this deviated from Beer's law when concentration exceeded 7 × 10 −5 M. Linear fitting of the absorbance concentration plot in the 1–7 × 10 −5 M concentration range gave a slope or molar extinction coefficient (ε) = 3.05 × 10 4 with a regression coefficient (R 2 ) of 0.9966 (Figure b). Noticeably, the obtained molar extinction coefficient was close to that reported for similar compounds and could be attributed to a better delocalization of electrons over the π‐conjugated molecules when thiophene or indandione were used as additional acceptor units …”

Section: Resultssupporting

confidence: 71%

Synthesis and photophysical studies on a new fluorescent phenothiazine‐based derivative

et al. 2020

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A new typical phenothiazine compound functionalized with thienyl-indandione derivative (PTZTID) was synthesized and characterized using spectral analysis (ultraviolet-visible (UV-vis) light, infrared (IR), 1 H nuclear magnetic resonance (NMR) and 13 C NMR tools). The UV-vis absorption spectra of the PTZTID solution in 1,4-dioxane showed two absorption bands attributed to localized aromatic π-π* transitions of conjugated aromatic moieties and intramolecular charge transfer with the characteristics of a π-π* transition. The fluorescence spectra exhibited a maximum emission wavelength at 580 nm. The effect of concentration on photophysical properties took the form of a minor hypsochromic shift, which was attributed to some extent to the occurrence of H-type aggregation of the PTZTID derivative. Binary solvent effects on the spectroscopic behaviour of PTZTID were measured at different H 2 O/1,4-dioxane ratios. Similarly, when increasing the water content, a hypsochromic shift was observed that resulted from H-type aggregation.Furthermore, geometry and electronic configurations of PTZTID were studied at density functional theory /B3LYP level and indicated that the compound had a nonplanar (butterfly structure). K E Y W O R D Scomputational studies, density functional theory, fluorescence, PTZTID

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Section: Resultssupporting

confidence: 71%

Synthesis and photophysical studies on a new fluorescent phenothiazine‐based derivative

et al. 2020

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“…The key intermediate 2 was synthesized by Vilsmeier reaction from compound 1 in a yield of 46%; the alkylthio substituted intermediate 4 was prepared in a yield of 68% by the selective Br/Li exchange in compound 3 and quenching the formed anion with N,N-dimethylformamide (DMF); [34,35] and the alkyl substituted aldehyde intermediate 6 was produced according to the reported method. [36] The dialdehyde precursors (7, 8, and 9) were synthesized by Stille coupling of bis(stannyl) compound 5 and monoaldehyde compounds (6, 2, or 4) in yields of ≈90%. Finally, Knoevenagel condensation of dialdehyde precursors 7, 8, and 9 with 1,1-dicyanomethylene-5,6-difluoro-3-indanone afforded the aimed acceptors IDTCN-C, IDTCN-O, and IDTCN-S in yields of 66%, 63%, and 61%, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…The facile synthetic routes of IDTCN‐C , IDTCN‐O, and IDTCN‐S are shown in Scheme . The key intermediate 2 was synthesized by Vilsmeier reaction from compound 1 in a yield of 46%; the alkylthio substituted intermediate 4 was prepared in a yield of 68% by the selective Br/Li exchange in compound 3 and quenching the formed anion with N , N ‐dimethylformamide (DMF); and the alkyl substituted aldehyde intermediate 6 was produced according to the reported method . The dialdehyde precursors ( 7 , 8, and 9 ) were synthesized by Stille coupling of bis(stannyl) compound 5 and monoaldehyde compounds ( 6 , 2, or 4 ) in yields of ≈90%.…”

Section: Resultsmentioning

confidence: 99%

High‐Efficiency As‐Cast Organic Solar Cells Based on Acceptors with Steric Hindrance Induced Planar Terminal Group

Liu

Yang

et al. 2019

Advanced Energy Materials

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A series of alkyl, alkoxyl, and alkylthio substituted A–π–D–π–A type nonfullerene acceptors (NFAs) IDTCN‐C, IDTCN‐O, and IDTCN‐S are designed and synthesized. The introduction of a lateral side chain at the outer position of the π bridge unit can endow the terminal moiety with a confined planar conformation due to the steric hindrance. Thus, compared with nonsubstituted NFA (IDTT2F), these acceptors tend to form favorable face‐on orientation and exhibit strong crystallinity as verified with grazing‐incidence wide‐angle X‐ray scattering measurement. Moreover, the variation of side chain can significantly change the lowest unoccupied molecular orbital (LUMO) energy level of acceptors. As state‐of‐the‐art NFAs, a power conversion efficiency of 13.28% (Voc = 0.91 V, Jsc = 19.96 mA cm−2, and FF = 73.2%) is obtained for the as‐cast devices based on IDTCN‐O, which is among the highest value reported in literature. The excellent photovoltaic performance for IDTCN‐O can be attributed to its slightly up‐shifted LUMO level and more balanced charge transport. This research demonstrates side chain engineering is an effective way to achieve high efficiency organic solar cells.

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“…The high ε values confirmed the π–π* characteristics of the ground‐excited electronic transition and attributed to a better delocalization of electrons. [ 40,41 ]…”

Section: Resultsmentioning

confidence: 99%

Synthesis, photophysical properties, and density functional theory studies of phenothiazine festooned vinylcyclohexenyl‐malononitrile

et al. 2020

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A novel phenothiazine derivative conjugated with vinylcyclohexenyl-malononitrile (PTZ-CDN) was synthesized through the Knoevenagel reaction of 10-octyl-10H-phenothiazine-3,7-dicarbaldehyde with 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile and fully characterized. The UV-vis absorption spectra of PTZ-CDN in different solvents showed a λ max band at 497-531 nm with a high molar extinction coefficient attributed to intramolecular charge transfer (ICT) with the characteristics of a π-π* transition. Increasing the solvent polarity resulted in a bathochromic shift of λ max. The PTZ-CDN fluorescence emission spectra were more sensitive to increasing the solvent polarity than the absorption spectra; they displayed a blue shift of λ em by 85 nm. To understand the behaviour of the PTZ-CDN derivative, Stokes' shift (Δ νÞ with respect to the solvent polarity, Lippert-Mataga and linear solvation-energy relationship (LSER) models were applied in which the LSER showed better regression than the Lippert-Mataga plots (r 2 = 0.9627). Finally, the TD-density functional theory (DFT) electronic transition spectra in dioxane and dimethyl formamide (DMF) were calculated. The DFT data showed that λ max resulted from the support of the highest occupied molecular orbital to the lowest unoccupied molecular orbital transition with 74% and 99% in dioxane and DMF, respectively.

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Effect of structural modification on the performances of phenothiazine-dye sensitized solar cells

Cited by 39 publications

References 58 publications

Synthesis and photophysical studies on a new fluorescent phenothiazine‐based derivative

Synthesis and photophysical studies on a new fluorescent phenothiazine‐based derivative

High‐Efficiency As‐Cast Organic Solar Cells Based on Acceptors with Steric Hindrance Induced Planar Terminal Group

Synthesis, photophysical properties, and density functional theory studies of phenothiazine festooned vinylcyclohexenyl‐malononitrile

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