A star-shaped sensitizer based on thienylenevinylene for dye-sensitized solar cells

Urbani, Maxence; Barea, Eva M.; Trevisan, Roberto; Aljarilla, Ana; Cruz, Pilar de la; Bisquert, Juan; Langa, Fernando

doi:10.1016/j.tetlet.2012.11.041

Cited by 6 publications

(4 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All the YD -series dyes show emission ranging from 639 to 686 nm. The Stokes shifts (110–858 cm –1 for YD22 – YD25 ; 305–513 cm –1 for YD26 – YD28 ) of these dyes were found to be relatively small compared to those of some metal-free dipolar organic dyes, ,− indicating a smaller energy required for geometrical reorganization of push–pull porphyrin dyes at photoexcited state.…”

Section: Results and Discussionmentioning

confidence: 94%

Influence of Phenylethynylene of Push–Pull Zinc Porphyrins on the Photovoltaic Performance

Chou

Reddy

et al. 2016

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

A series of zinc porphyrin dyes YD22-YD28 were synthesized and used for dye-sensitized solar cells. Dyes YD26-YD28 consist of zinc porphyrin (ZnP) as core unit, arylamine (Am) as electron-donating group, and p-ethynylbenzoic acid (EBA) as an electron-withdrawing/-anchoring group. The dyes YD22-YD25 contain additional phenylethynylene group (PE) bridged between Am and ZnP units. The influence of the PE unit on molecular properties as well as photovoltaic performances were investigated via photophysical and electrochemical studies and density functional calculations. With the insertion of PE unit, the dyes YD22-YD25 possess better light-harvesting properties in terms of significantly red-shifted Q-band absorption. The conversion efficiencies for dyes YD22-YD25 are better than those of dyes YD26-YD28 owing to larger J(SC) output. Natural transition orbitals and Mulliken charge analysis were used to analyze the electron injection efficiency for porphyrin dyes upon time-dependent DFT calculations. The results indicated that insertion of additional PE unit is beneficial to higher J(SC) by means of improved light-harvesting property due to broadened and red-shifted absorption.

show abstract

Section: Results and Discussionmentioning

confidence: 94%

Influence of Phenylethynylene of Push–Pull Zinc Porphyrins on the Photovoltaic Performance

Chou

Reddy

et al. 2016

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

show abstract

“…Push-pull type sensitizers with electron-withdrawing bridge groups have been explored, and molecular photoswitches have been studied with the intent to control sensitizer function by external stimuli . Structural changes in the bridge have been used to tune IET and recombination by “conformational trapping.” Several studies involved chromophores that contained multiple anchor groups − or star-shaped molecules. − However, in these examples, all anchor groups served the same function. The concept of employing multiple linkers with different functions, for example, one linker for stable chemical attachment to the surface and another one for promoting interaction between the sensitizer and the interface, is an approach that gives more flexibility in the design of sensitizers and can add functionalities beyond IET.…”

Section: Introductionmentioning

confidence: 99%

Conformational and Binding Effects on Interfacial Electron Transfer from Dual-Linker Sensitizers

et al. 2021

View full text Add to dashboard Cite

Interfacial electron transfer (IET) between novel dual-linker perylenes and TiO 2 was investigated by ultrafast spectroscopy and nonadiabatic quantum mechanics/molecular mechanics (QM/MM) simulations. The influence of the number of linkers (one vs two) and their substitution position (ortho vs peri) on IET was investigated. Perylene sensitizers derivatized with two acrylic acid linkers in the peri position, pDtBuPe-(C 2 H 2 COOH) 2 (bis-peri), and in the ortho position, oDtBuPe-(C 2 H 2 COOH) 2 (bis-ortho), were compared to their single-linker counterparts: pDtBuPeC 2 H 2 COOH (peri) and oDtBu-PeC 2 H 2 COOH (ortho). MM simulations of the bis-peri and bisortho sensitizers predicted that, in both cases, only one linker binds covalently to the {101} surface of anatase TiO 2 , while the second one binds weakly via vdW or hydrogen-bonding interactions. Results from QM/MM simulations corroborated experimental injection times for all compounds, thereby supporting single-linker binding to the surface for the dual-linker sensitizers. The study showed that, surprisingly, IET from bis-peri was significantly slower than that from peri. Theory attributes this behavior to small conformational changes caused by steric interactions. The degrees of freedom that are most strongly correlated with variations in IET times were identified by principal component analysis. Comparison between bis-ortho and ortho showed, as expected, that the dual-linker sensitizer injects faster than the single-linker variant. However, the influence of the substitution position on IET was much smaller than expected based on the difference in the static electronic structure. Finally, the strong effect of conformational changes on IET was also observed experimentally in modulations of IET due to coupling to vibrational modes, in excellent agreement with the QM/MM simulations. This study shows that small conformational changes and vibrational coupling can have a significant influence on IET even on the femtosecond time scale. The addition of linkers that differ in bonding strength and serve different functions opens up new avenues for controlling IET dynamics.

show abstract

“…[7][8][9][10] Whereas many push-pull sensitizers based on this model have been synthesized, examples of sensitizers with a simple p-A structure namely devoid of terminal donor group remain scarce. [12][13][14][15][16][17][18][19] Thiophene oligomers (nTs) have been frequently used p-conjugating spacers in D-p-A sensitizers, [7][8][9] but there are very few examples of sensitizers based on pure nTs. Thus, a PCE of 3.36% was obtained with a quinquethiophene derivative with two carboxylic groups.…”

Section: Introductionmentioning

confidence: 99%

“…During the past decade, a huge number of metal-free sensitizers have been synthesized and evaluated in DSSCs cells and PCE exceeding 10.0% have been reported. [12][13][14][15][16][17][18][19] Thiophene oligomers (nTs) have been frequently used a π-conjugating spacers in Dπ-A sensitizers, 7-9 but there are very few examples of sensitizers based on pure nTs. 11,12 Most of metal-free sensitizers possess a D-π-A structure where "D" represents an electron-donating moiety such as a diarylamine or carbazole, "π" a π-conjugating spacer and "A" an electron-accepting moiety.…”

mentioning

confidence: 99%

Linearly π-conjugated oligothiophenes as simple metal-free sensitizers for dye-sensitized solar cells

et al. 2015

View full text Add to dashboard Cite

International audience

Four linear oligothiophenes containing 4, 5 and 7 thiophene rings substituted by a variable number of octyl chains attached at the beta-position of some of the thiophene rings and possessing a terminal cyanoacrylic acid anchoring group have been synthesized. Results of UV-Vis absorption spectroscopy and cyclic voltammetry show that as expected the extension of the π-conjugated system leads to a decrease of the optical gap with an increase of the HOMO level. The four compounds have been evaluated as sensitizers in dye-sensitized solar cells (DSSCs) using a iodide/triiodide liquid electrolyte and the results are discussed in terms of the structure–property relationship with regard to the extension of the conjugated system and the number and position of the octyl side chains using N719 as the reference system. A power conversion efficiency of ~7.30% corresponding to 90% of the value given by N719 under identical conditions has been obtained with one of the heptamers.

show abstract

A star-shaped sensitizer based on thienylenevinylene for dye-sensitized solar cells

Cited by 6 publications

References 38 publications

Influence of Phenylethynylene of Push–Pull Zinc Porphyrins on the Photovoltaic Performance

Influence of Phenylethynylene of Push–Pull Zinc Porphyrins on the Photovoltaic Performance

Conformational and Binding Effects on Interfacial Electron Transfer from Dual-Linker Sensitizers

Linearly π-conjugated oligothiophenes as simple metal-free sensitizers for dye-sensitized solar cells

Contact Info

Product

Resources

About