A bis(diketopyrrolopyrrole) dimer-containing ligand in platinum(<scp>ii</scp>) polyyne oligomers exhibiting ultrafast photoinduced electron transfer with PCBM and solar cell properties

Nos, Melodie; Marineau-Plante, Gabriel; Gao, Di; Durandetti, Muriel; Hardouin, Julie; Karsenti, Paul‐Ludovic; Gupta, Gaurav; Sharma, Ganesh D.; Harvey, Pierre D.; Lemouchi, Cyprien; Pluart, Loïc Le

doi:10.1039/c9tc03487k

Cited by 7 publications

(26 citation statements)

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“…They are, respectively, shifted by 0.13 and −0.38 ppm for PA , and 0.20 and −0.35 for PB and PC (Figures S27–S29, SI). Those observations are in good agreement with the previously reported 1 H NMR data concerning the analogue P1 . For PA , PB , and PC , one signal is observed at 3.80 ppm in the 1 H decoupled 31 P NMR spectra, it is flanked by 195 Pt satellites with coupling constants J ( 31 P– 195 Pt) of 2299, 2302,, and 2312 Hz, respectively (Figures S22, S24, and S26, SI).…”

Section: Resultssupporting

confidence: 92%

“…Then, the triisopropylsilyl (TIPS) protected triple bonds were introduced using a Sonogashira coupling reaction with (triisopropylsilyl)acetylene and 4 . Unlike our previous work, TIPS groups were chosen for their enhanced robustness compared to trimethylsilyl (TMS). Moreover, they turned out to be more compatible with the various reaction conditions used and significantly increased the stability of the compounds.…”

Section: Resultsmentioning

confidence: 99%

“…The charge mobilities, cyclic voltammograms, and photophysical properties of these polymers were studied. The efficiency of the active layer in solar cells was also evaluated, but the devices exhibited modest photoconversion efficiencies until recently when a very promising 9.54% has been obtained . Great effort has been devoted to studying the impact of the self-assembly of DPP − and [Pt]- based − homopolymers on their electronic, optical, and photophysical properties.…”

Section: Introductionmentioning

confidence: 99%

“…We report the synthesis of three ( [Pt] -DPP) n polymers ( PA , PB , and PC ) bearing various mesogenic side groups. Their properties are compared to a polymer deprived of any organizing side groups ( P1 ) whose synthesis was previously reported (Scheme ). Cyanobiphenyl ( LA , PA ), − alkyloxybiphenyl ( LB , PB ), and triphenylene ( LC , PC ) − side groups were selected for their demonstrated ability to promote self-assembly in various cases (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

“… a Synthetic schemes of PA , PB , and PC platinum(II) polyyne oligomers with molecular structures of L1 and P1 from ref . …”

Section: Introductionmentioning

confidence: 99%

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Effect of Mesogenic Side Groups on the Redox, Photophysical, and Solar Cell Properties of Diketopyrrolopyrrole-trans-bis(diphosphine)diethynylplatinum(II) Polymers

Marineau-Plante

Nos

Gao

et al. 2021

ACS Appl. Polym. Mater.

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Three ([Pt]-DPP) n polymers PA, PB, and PC bearing cyanobiphenyl, alkyloxyphenyl, and triphenylene self-assembling groups were synthesized. The optical, electrochemical, photophysical, and solar cell properties were investigated and compared to analogue polymer P1 deprived of any organizing group. Significant differences lie in the more stabilized lowest unoccupied molecular orbital (LUMO) level for PA and the highest occupied molecular orbital (HOMO) level for PC. X-ray diffraction analyses on thin films evidenced π-aggregation of molecules for PA and PB. Nanosecond timescale fluorescent lifetimes were measured for PA, PB, and PC. An ultrafast photoinduced electron transfer between these polymers and phenyl-C61-butyric acid methyl ester (PC61BM) was brought out from femtosecond transient absorption spectroscopy (fs-TAS). It is faster for PC than for PA and PB. The recombination leads to singlet- and triplet-state formation (([Pt]-DPP) n )•+ + PC61BM•– → 3([Pt]-DPP) n * + ([Pt]-DPP) n + PC61BM. Solar cells were fabricated using polymers blended with an acceptor (PC71BM or IT-4F) as an active layer in conventional device structure indium tin oxide (ITO)/poly(3,4-ethylenedioxythiophene):polystyrene sulfonate (PEDOT:PSS)/active layer/poly[(9,9-dioctyl-2,7-fluorene)-alt-(9,9-bis(3′-(N,N-dimethylamino)propyl)-2,7-fluorene)] (PFN)/Al. Unlike PA, polymers PB and PC exhibit better photovoltaic performances than P1. Higher power conversion efficiencies (PCEs) were reached with IT-4F, PB:IT-4F (PCE = 10.83%, J sc = 17.83 mA cm–2, V oc = 0.98 V), and PC:IT-4F (PCE = 13.26%, J sc = 18.95 mA cm–2, V oc = 1.06 V). This work highlights the beneficial impact of triphenylene self-assembling groups on photovoltaic properties. PC exhibits a record-high PCE (13.26%) for [Pt]-containing polyyne oligomers and small molecules.

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Section: Resultssupporting

confidence: 92%

Section: Resultsmentioning

confidence: 99%