Triphenylamine-Based Push-Pull σ-C60 Dyad As Photoactive Molecular Material for Single-Component Organic Solar Cells: Synthesis, Characterizations, and Photophysical Properties

Antoine Labrunie; Julien Gorenflot; Maxime Babics; Olivier Alévêque; Sylvie Dabos-Seignon; Ahmed H. Balawi; Zhipeng Kan; Markus Wohlfahrt; Eric Levillain; Piétrick Hudhomme; Pierre M. Beaujuge; Frédéric Laquai; Clément Cabanetos; Philippe Blanchard

doi:10.1021/acs.chemmater.8b01117

Triphenylamine-Based Push-Pull σ-C₆₀ Dyad As Photoactive Molecular Material for Single-Component Organic Solar Cells: Synthesis, Characterizations, and Photophysical Properties

Antoine Labrunie, Julien Gorenflot, Maxime Babics, Olivier Alévêque, Sylvie Dabos-Seignon, Ahmed H. Balawi, Zhipeng Kan, Markus Wohlfahrt, Eric Levillain, Piétrick Hudhomme, Pierre M. Beaujuge, Frédéric Laquai^*, Clément Cabanetos, Philippe Blanchard

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

53 Scopus citations

Abstract

A push-pull σ-C₆₀ molecular dyad was synthesized via Huisgen-type click chemistry and used as photoactive material for single-component organic solar cells. Steady-state photoluminescence (PL) experiments of the dyad in solution show a significant quenching of the emission of the push-pull moiety. Spin-casting of a solution of the dyad results in homogeneous and smooth thin films, which exhibit complete PL quenching in line with ultrafast photoinduced electron-transfer in the solid state. Spectroelectrochemistry reveals the optical signatures of radical cations and radical anions. Evaluation of the charge carrier mobility by space-charge limited current measurements gives an electron-mobility of μ_e = 4.3 × 10^-4 cm² V^-1 s^-1, ca. 50 times higher than the hole-mobility. Single-component organic solar cells yield an open-circuit voltage V_oc of 0.73 V and a short-circuit current density of 2.1 mA cm^-2 however, a poor fill factor FF (29%) is obtained, resulting in low power conversion efficiency of only 0.4%. Combined transient absorption (TA) and time-delayed collection field (TDCF) experiments show mostly ultrafast photon-to-charge conversion and a small component of diffusion-limited exciton dissociation, revealing the presence of pure fullerene domains. Furthermore, a strong field dependence of charge generation is observed, governing the device fill factor, which is further reduced by a competition between extraction and fast recombination of separated charges.

Original language	English (US)
Pages (from-to)	3474-3485
Number of pages	12
Journal	Chemistry of Materials
Volume	30
Issue number	10
DOIs	https://doi.org/10.1021/acs.chemmater.8b01117
State	Published - May 22 2018

Bibliographical note

Funding Information:
The RFI LUMOMAT from the Reǵ ion Pays de la Loire is acknowledged for the PhD grant of A. Labrunie. We thank also the PIAM (Plateforme d’Ingeńierie et Analyses Molećulaires) of the University of Angers for the characterization of organic compounds and R. Mallet, from the SCIAM of the University of Angers for TEM experiments. Jonhson Mattey is acknowledged for the gift of PdCl2 used for the preparation of Pd(PPh3)4 catalyst. The research reported in this publication was supported by funding from King Abdullah University of Science and Technology (KAUST). M.W. acknowledges a VSRP internship from KAUST.

Publisher Copyright:
Copyright © 2018 American Chemical Society.

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering
Materials Chemistry

Access to Document

10.1021/acs.chemmater.8b01117

Cite this

Labrunie, A., Gorenflot, J., Babics, M., Alévêque, O., Dabos-Seignon, S., Balawi, A. H., Kan, Z., Wohlfahrt, M., Levillain, E., Hudhomme, P., Beaujuge, P. M., Laquai, F., Cabanetos, C., & Blanchard, P. (2018). Triphenylamine-Based Push-Pull σ-C₆₀ Dyad As Photoactive Molecular Material for Single-Component Organic Solar Cells: Synthesis, Characterizations, and Photophysical Properties. Chemistry of Materials, 30(10), 3474-3485. https://doi.org/10.1021/acs.chemmater.8b01117

@article{686cfee6522f4d2dad355aa91fa6f47d,

title = "Triphenylamine-Based Push-Pull σ-C60 Dyad As Photoactive Molecular Material for Single-Component Organic Solar Cells: Synthesis, Characterizations, and Photophysical Properties",

abstract = "A push-pull σ-C60 molecular dyad was synthesized via Huisgen-type click chemistry and used as photoactive material for single-component organic solar cells. Steady-state photoluminescence (PL) experiments of the dyad in solution show a significant quenching of the emission of the push-pull moiety. Spin-casting of a solution of the dyad results in homogeneous and smooth thin films, which exhibit complete PL quenching in line with ultrafast photoinduced electron-transfer in the solid state. Spectroelectrochemistry reveals the optical signatures of radical cations and radical anions. Evaluation of the charge carrier mobility by space-charge limited current measurements gives an electron-mobility of μe = 4.3 × 10-4 cm2 V-1 s-1, ca. 50 times higher than the hole-mobility. Single-component organic solar cells yield an open-circuit voltage Voc of 0.73 V and a short-circuit current density of 2.1 mA cm-2 however, a poor fill factor FF (29%) is obtained, resulting in low power conversion efficiency of only 0.4%. Combined transient absorption (TA) and time-delayed collection field (TDCF) experiments show mostly ultrafast photon-to-charge conversion and a small component of diffusion-limited exciton dissociation, revealing the presence of pure fullerene domains. Furthermore, a strong field dependence of charge generation is observed, governing the device fill factor, which is further reduced by a competition between extraction and fast recombination of separated charges.",

author = "Antoine Labrunie and Julien Gorenflot and Maxime Babics and Olivier Al{\'e}v{\^e}que and Sylvie Dabos-Seignon and Balawi, {Ahmed H.} and Zhipeng Kan and Markus Wohlfahrt and Eric Levillain and Pi{\'e}trick Hudhomme and Beaujuge, {Pierre M.} and Fr{\'e}d{\'e}ric Laquai and Cl{\'e}ment Cabanetos and Philippe Blanchard",

note = "Funding Information: The RFI LUMOMAT from the Reǵ ion Pays de la Loire is acknowledged for the PhD grant of A. Labrunie. We thank also the PIAM (Plateforme d{\textquoteright}Inge{\'n}ierie et Analyses Mole{\'c}ulaires) of the University of Angers for the characterization of organic compounds and R. Mallet, from the SCIAM of the University of Angers for TEM experiments. Jonhson Mattey is acknowledged for the gift of PdCl2 used for the preparation of Pd(PPh3)4 catalyst. The research reported in this publication was supported by funding from King Abdullah University of Science and Technology (KAUST). M.W. acknowledges a VSRP internship from KAUST. Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = may,

day = "22",

doi = "10.1021/acs.chemmater.8b01117",

language = "English (US)",

volume = "30",

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Labrunie, A, Gorenflot, J, Babics, M, Alévêque, O, Dabos-Seignon, S, Balawi, AH, Kan, Z, Wohlfahrt, M, Levillain, E, Hudhomme, P, Beaujuge, PM, Laquai, F, Cabanetos, C & Blanchard, P 2018, 'Triphenylamine-Based Push-Pull σ-C₆₀ Dyad As Photoactive Molecular Material for Single-Component Organic Solar Cells: Synthesis, Characterizations, and Photophysical Properties', Chemistry of Materials, vol. 30, no. 10, pp. 3474-3485. https://doi.org/10.1021/acs.chemmater.8b01117

Triphenylamine-Based Push-Pull σ-C₆₀ Dyad As Photoactive Molecular Material for Single-Component Organic Solar Cells: Synthesis, Characterizations, and Photophysical Properties. / Labrunie, Antoine; Gorenflot, Julien; Babics, Maxime et al.
In: Chemistry of Materials, Vol. 30, No. 10, 22.05.2018, p. 3474-3485.

Research output: Contribution to journal › Article › peer-review

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T2 - Synthesis, Characterizations, and Photophysical Properties

AU - Labrunie, Antoine

AU - Gorenflot, Julien

AU - Babics, Maxime

AU - Alévêque, Olivier

AU - Dabos-Seignon, Sylvie

AU - Balawi, Ahmed H.

AU - Kan, Zhipeng

AU - Wohlfahrt, Markus

AU - Levillain, Eric

AU - Hudhomme, Piétrick

AU - Beaujuge, Pierre M.

AU - Laquai, Frédéric

AU - Cabanetos, Clément

AU - Blanchard, Philippe

N1 - Funding Information: The RFI LUMOMAT from the Reǵ ion Pays de la Loire is acknowledged for the PhD grant of A. Labrunie. We thank also the PIAM (Plateforme d’Ingeńierie et Analyses Molećulaires) of the University of Angers for the characterization of organic compounds and R. Mallet, from the SCIAM of the University of Angers for TEM experiments. Jonhson Mattey is acknowledged for the gift of PdCl2 used for the preparation of Pd(PPh3)4 catalyst. The research reported in this publication was supported by funding from King Abdullah University of Science and Technology (KAUST). M.W. acknowledges a VSRP internship from KAUST. Publisher Copyright: Copyright © 2018 American Chemical Society.

PY - 2018/5/22

Y1 - 2018/5/22

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