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A bis(diketopyrrolopyrrole) dimer-containing ligand in platinum(II) polyyne oligomer exhibiting ultrafast photoinduced electron transfer with PCBM and solar cell properties

Melodie Nos 1 Gabriel Marineau-Plante 2 Di Gao 1 Muriel Durandetti 3 Julie Hardouin 4, 5 Paul-Ludovic Karsenti 2 Gaurav Gupta 6 Ganesh Datt Sharma 6 Pierre Harvey 2 Cyprien Lemouchi 1 Loïc Le Pluart 1
1 LCMT - Laboratoire de chimie moléculaire et thioorganique
2 UdeS - Université de Sherbrooke
3 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
4 PBS - Polymères Biopolymères Surfaces
5 Plate-forme de Protéomique PISSARO
6 LMNIIT - LNM Institute of Information Technology
Abstract : Two polyyne oligomers using the thiophene–(diketopyrrolopyrrole)–thiophene unit, T–DPP–T, and the organometallic synthon trans-Pt(PBu3)2(C[triple bond, length as m-dash]C)2, [Pt], ([L1]–[Pt])m (P1), here used for comparison purposes, and ([L4]–[Pt])m (P4), where L1 and L4 are T–DPP–T and (T–DPP–T)2, respectively, were synthesized by CuI-catalyzed dehydrohalogenation and fully characterized. The optical and electrochemical properties were investigated by UV-visible absorption and cyclic voltammetry, and P4 was found to exhibit a very low band gap. DFT (density functional theory) and TD-DFT (time-dependent DFT) computations were undertaken to address the polymers’ geometry, their electronic structures and calculated HOMO and LUMO energies. The S1 level is best described as a ππ* excited state. P1 and P4 exhibit fluorescence lifetime in ps timescale and the fs-TAS data indicate an ultrafast electron transfer to PC61BM ((1Px* + PC61BM → Px+˙ + (PC61BM)−˙; time scale < 113–128 fs) evidenced by an increased formation of the triplet state upon back electron transfer (Px+˙ + (PC61BM)−˙) → 1,3Px* + PC61BM; x = 1, 4). The timescale of recombination for P4 (P4+˙ + (PC61BM)−˙ → 3P4* + PCBM) is found to be ∼3 ps. The photovoltaic performance of Px was investigated by fabricating the photovoltaic solar cells (PSCs) with conventional device structure ITO/PEDOT:PSS/(P1 or P4):PC71BM/PFN/Al. After solvent vapour annealing with THF, the power conversion efficiencies, PCEs, are 7.36% (P1; Jsc = 12.94 mA cm−2, Voc = 0.92 V, FF = 0.62) and 9.54% (P4; Jsc = 16.24 mA cm−2, Voc = 0.89 V, FF = 0.66). The higher PCE of P4 may be related to the faster extraction and longer charge carrier lifetime for P4 based PSCs as compared to P1.
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Journal articles
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02431901
Contributor : Madeleine Roux-Merlin <>
Submitted on : Wednesday, January 8, 2020 - 11:22:34 AM
Last modification on : Friday, April 16, 2021 - 10:40:04 AM

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COMUE-NORMANDIE | INC-CNRS | INSA-ROUEN | UNIROUEN | ENSICAEN | LCMT | COBRA | INSA-GROUPE | UNICAEN | CNRS | PBS | UNILEHAVRE

Citation

Melodie Nos, Gabriel Marineau-Plante, Di Gao, Muriel Durandetti, Julie Hardouin, et al.. A bis(diketopyrrolopyrrole) dimer-containing ligand in platinum(II) polyyne oligomer exhibiting ultrafast photoinduced electron transfer with PCBM and solar cell properties. Journal of Materials Chemistry C, Royal Society of Chemistry, 2020, 8 (7), pp.2363-2380. ⟨10.1039/C9TC03487K⟩. ⟨hal-02431901⟩

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