Cyanoacrylic- and (1-cyanovinyl)phosphonic acid anchoring ligands for application in copper-based dye-sensitized solar cells

Baumgartner, Yann; Klein, Y. Maximilian; Constable, Edwin C.; Housecroft, Catherine E.; Willgert, Markus

doi:10.1039/c6ra20375b

Cited by 11 publications

(12 citation statements)

References 41 publications

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“…Electrochemical impedance spectroscopy (EIS) has become a fundamental tool for investigating the electrochemical properties of DSCs. 22,23,54,55,56,57,58,59 Key parameters that can be determined with the help of fitting circuit models are the recombination resistance (R rec ), transport resistance (R tr ) and chemical capacitance (C μ ). A common way to display the EIS measurements is using a Nyquist plot (Fig.…”

Section: Electrochemical Impedance Spectroscopy (Eis): Introductionmentioning

confidence: 99%

The way to panchromatic copper(i)-based dye-sensitized solar cells: co-sensitization with the organic dye SQ2

et al. 2017

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Section: Electrochemical Impedance Spectroscopy (Eis): Introductionmentioning

confidence: 99%

The way to panchromatic copper(i)-based dye-sensitized solar cells: co-sensitization with the organic dye SQ2

et al. 2017

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“…The second design feature to consider is the anchoring domain. Of the different anchors that we have investigated in copper(I) dyes, phosphonic acids (or phosphonates because the protonation state of the adsorbed anchor is not clear [39]) with a phenyl spacer between the PO(OH) 2 and bpy units are superior to carboxylic and cyanoacrylic acids if one considers both synthetic accessibility and DSSC performance [40][41][42]. Finally, we come to the ancillary ligand where there is near-infinite scope for functional group modification.…”

Section: Introductionmentioning

confidence: 99%

The Versatile SALSAC Approach to Heteroleptic Copper(I) Dye Assembly in Dye-Sensitized Solar Cells

2018

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Surface-bound heteroleptic copper(I) dyes [Cu(L anchor )(L ancillary )] + are assembled using the "surfaces-as-ligands, surfaces as complexes" (SALSAC) approach by three different procedures. The anchoring and ancillary ligands chosen are ((6,6 -dimethyl-[2,2 -bipyridine]-4,4 -diyl)-bis(4,1-phenylene))bis(phosphonic acid) (3) and 4,4 -bis(4-iodophenyl)-6,6 -diphenyl-2,2 -bipyridine (4), respectively. In the first SALSAC procedure, the FTO/TiO 2 electrode is functionalized with 3 in the first dye bath, and then undergoes ligand exchange with the homoleptic complex [Cu (4)

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“…The phosphonic acid anchoring ligand 6 (Scheme 6) was chosen because it exhibits enhanced binding to TiO 2 with respect to carboxylic acids [24]. Taking both DSC performance and efficient ligand synthesis into account, we have previously established that copper(I) dyes with phosphonic acid or phosphonate anchors [37] containing a phenylene spacer between the anchor and copper-binding domains are favored over those with carboxylic acid (or carboxylate) and cyanoacrylic acid (or cyanoacrylate) anchors [34,38,39]. The solid-state absorption spectra of the dye-functionalized electrodes are shown in Figure 8.…”

Section: Solar Cell Fabrication and Performancesmentioning

confidence: 99%

Schiff Base Ancillary Ligands in Bis(diimine) Copper(I) Dye-Sensitized Solar Cells

Lüthi

Cortés

Prescimone

et al. 2020

IJMS

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Five 6,6′-dimethyl-2,2′-bipyridine ligands bearing N-arylmethaniminyl substituents in the 4- and 4′-positions were prepared by Schiff base condensation in which the aryl group is Ph (1), 4-tolyl (2), 4-tBuC6H4 (3), 4-MeOC6H4 (4), and 4-Me2NC6H4 (5). The homoleptic copper(I) complexes [CuL2][PF6] (L = 1–5) were synthesized and characterized, and the single crystal structure of [Cu(1)2][PF6]·Et2O was determined. By using the “surfaces-as-ligands, surfaces-as-complexes” (SALSAC) approach, the heteroleptic complexes [Cu(6)(Lancillary)]+ in which 6 is the anchoring ligand ((6,6′-dimethyl-[2,2′-bipyridine]-4,4′-diyl)bis(4,1-phenylene))bis(phosphonic acid)) and Lancillary = 1–5 were assembled on FTO-TiO2 electrodes and incorporated as dyes into n-type dye-sensitized solar cells (DSCs). Data from triplicate, fully-masked DSCs for each dye revealed that the best-performing sensitizer is [Cu(6)(1)]+, which exhibits photoconversion efficiencies (η) of up to 1.51% compared to 5.74% for the standard reference dye N719. The introduction of the electron-donating MeO and Me2N groups (Lancillary = 4 and 5) is detrimental, leading to a decrease in the short-circuit current densities and external quantum efficiencies of the solar cells. In addition, a significant loss in open-circuit voltage is observed for DSCs sensitized with [Cu(6)(5)]+, which contributes to low values of η for this dye. Comparisons between performances of DSCs containing [Cu(6)(1)]+ and [Cu(6)(4)]+ with those sensitized by analogous dyes lacking the imine bond indicate that the latter prevents efficient electron transfer across the dye.

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Cyanoacrylic- and (1-cyanovinyl)phosphonic acid anchoring ligands for application in copper-based dye-sensitized solar cells

Abstract: Replacing phosphonic acid by (1-cyanovinyl)phosphonic acid anchors in heteroleptic bis(diimine)copper(i) dyes in DSCs gives a gain in JSC; a dye with a bpy-based anchor gives improved performance over one with a phen-based anchor.

Cited by 11 publications

References 41 publications

The way to panchromatic copper(i)-based dye-sensitized solar cells: co-sensitization with the organic dye SQ2

The way to panchromatic copper(i)-based dye-sensitized solar cells: co-sensitization with the organic dye SQ2

The Versatile SALSAC Approach to Heteroleptic Copper(I) Dye Assembly in Dye-Sensitized Solar Cells

Schiff Base Ancillary Ligands in Bis(diimine) Copper(I) Dye-Sensitized Solar Cells

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