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Effect of different acceptors on N-hexyl carbazole moiety for dye-sensitized solar cells: design, characterization, molecular structure, and DSSC fabrications

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Abstract

Hexyl carbazole derivatives are one of the most prominent dye scaffolds in the dye-sensitized solar cells (DSSCs). New substituted carbazole dyes such as DRA-HC, DCA-HC, and DTC-HC were synthesized for DSSCs. These dyes are containing hexyl moiety as electron donor and rhodanine-3-acetic acid, cyanoacetic acid and tetracyanoethylene as an electron acceptor linked to carbazole moiety. The relation between dye structures, photophysical/electrochemical, molecular structure and DSSC manufacturing had been discussed. All structures showed more positive ground-state oxidation potential than I−/I−3 and more negative excited state oxidation potential than the conduction band edge of the semiconductor. The highest efficiency of the DSSCs was obtained in the case of DCA-HC dye (η = 1.41%, VOC = 708 mV, FF = 0.81, and JSC = 2.45 mA cm−2 with 100 mW cm−2) compared to other synthesized dyes.

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Abbreviations

DRA-HC:

2,2′-(((9-Hexyl-9H-carbazole-3,6-diyl)bis(methanylylidene))bis(4-oxo-2-thioxothiazolidin-3-yl-5-ylidene))diacetic acid

DCA-HC:

3-(6-(2-Carboxy-2-cyanovinyl)-9-hexyl-9H-carbazol-3-yl)-2-cyanoacrylic acid

DTC-HC:

2,2′-((((9-Hexyl-9H-carbazole-3,6-diyl)bis(methanylylidene))bis(hydrazin-1-yl-2-ylidene))bis(4,1-phenylene))bis(ethene-1,1,2-tricarbonitrile)

DSSCs:

Dye-sensitized solar cells

V OC :

Open-circuit voltage

J SC :

Short-circuit current density

D–π–A:

Donor–(π-conjugated spacer)–acceptor

TCNE:

Tetracyanoethylene

TLC:

Thin-layer chromatography

KBr:

Potassium bromide

SEM:

Scanning electron microscopy

CV:

Cyclic voltammetry techniques

TBP:

4-Tertbutylpyridine

ε :

Molar absorptivity

E 0–0 :

Band gap

E LUMO :

Lowest unoccupied molecular orbital

τe:

Electron lifetime

IP:

Ionization potential

η :

Absolute hardness

ω :

Electrophilicity index

ΔE :

Separation energy

S :

Global softness

η :

Power conversion efficiency

FF:

Fill factor

TiO2 :

Titanium dioxide

ICT:

Intermolecular charge transfer

TBAI:

Tetra-n-butylammonium iodide

DMSO-d6 :

Deuterated dimethyl sulfoxide

UV–Vis:

Ultraviolet–visible

EIS:

Electrochemical impedance spectroscopy

FTO:

Fluorine-doped tin oxide

DMF:

Dimethyl formamide

E ox :

Redox potentials

E HOMO :

Highest occupied molecular orbital

J–V :

Current–voltage density

TMS:

Tetra-methyl silane

σ :

Absolute softness

EA:

Electron affinity

ΔN max :

Maximum amount of electron transfer

χ :

Absolute electronegativity

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt

    Moustafa S. Abusaif, Mohamed R. Selim & Yousry A. Ammar

  2. Polymeric Materials Research Department, Advanced Technology and New Materials Research Institute, City of Scientific Research and Technological Applications (SRTA-City), New Borg El-Arab City, Alexandria, 21934, Egypt

    M. A. Abu-Saied

  3. Electronic Materials Department, Advanced Technology and New Materials Research Institute, City of Scientific Research and Technological Applications (SRTA-City), New Borg El-Arab City, Alexandria, 21934, Egypt

    M. Fathy & A. B. Kashyout

  4. Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt

    Ahmed A. El-Sherif

Authors
  1. Moustafa S. Abusaif
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  2. M. A. Abu-Saied
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  3. M. Fathy
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  4. Ahmed A. El-Sherif
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Correspondence to Ahmed A. El-Sherif.

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Abusaif, M.S., Abu-Saied, M.A., Fathy, M. et al. Effect of different acceptors on N-hexyl carbazole moiety for dye-sensitized solar cells: design, characterization, molecular structure, and DSSC fabrications. J IRAN CHEM SOC 18, 949–960 (2021). https://doi.org/10.1007/s13738-020-02082-y

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  • DOI: https://doi.org/10.1007/s13738-020-02082-y

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