Facile synthesis of metal-free organic dyes featuring a thienylethynyl spacer for dye sensitized solar cells

Al-Eid, Manal; Lim, Sung‐Hwan; Park, Kwang Won; Fitzpatrick, Brian; Han, Chi Hwan; Kwak, Kyungwon; Hong, Jongin; Cooke, Graeme

doi:10.1016/j.dyepig.2014.01.004

Cited by 43 publications

(26 citation statements)

References 21 publications

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“…Recently the precursor aldehyde 5 was reported by Cooke and collaborators through the Sonogashira coupling in 40% yield using different experimental conditions (Pd/C (10%); CuI, Ph 3 P, K 2 CO 3 , H 2 O/DME (1:1) [51]. However, the same compound 5 was prepared by us in a much higher yield (77%) using different reaction conditions (Pd(PPh 3 ) 2 Cl 2 , CuI, TEA, THF).…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells

Fernandes

Mesquita

Andrade

et al. 2017

Organic Electronics

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a b s t r a c tFive push-pull heterocyclic dyes 4e7, and 9 were synthesized and characterized in order to study the variations in the optical, electronic and photovoltaic properties induced by structural modifications, i.e. different spacer units and anchoring groups. The final push-pull conjugated dyes 6e7 and 9 are formed by a N,N-dimethylaniline donor moiety conjugated with bithiophene, ethynyl-bithiophene or ethynylthieno[3,2-b]thiophene spacers and cyanoacetic acid or rhodanine-3-acetic acid as anchoring group. The synthesis of the precursor aldehydes 4e5 was accomplished through a Sonogashira coupling, on the other hand, compound 8 was prepared by Suzuki coupling. Knoevenagel condensation of aldehydes 4, 5 and 8 with cyanoacetic acid or rhodamine-3-acetic acid afforded the final push-pull dyes 6, 7 and 9. Information on conformation, electronic structure and electron distribution was obtained by DFT and TDDFT calculations. This multidisciplinary study regarding the evaluation of the optical, redox and photovoltaic properties of the dyes reveals that compound 7, bearing an ethynyl-bithiophene spacer conjugated with a cyanoacetic acid anchoring group, has the highest conversion efficiency (3.51%) as dye sensitizer in nanocrystalline TiO 2 solar cells. Co-adsorption studies were also performed for dyes 6e7 with N719 as co-adsorbent, and this enhanced dye efficiencies by 33e45%. The best cell performance was obtained by co-adsorbing N719 and dye 7 (75/25 vol%) with 4.66% efficiency.

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Section: Synthesis and Characterizationmentioning

confidence: 99%

Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells

Fernandes

Mesquita

Andrade

et al. 2017

Organic Electronics

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“…27 On the other hand, the increase of the overall conversion efficiency of the DSSC (η) 5b to double value that of 5a can be ascribed to the better donating ability of this dye compared to dye 5a. The promising results; J SC values (2.46 × 10 -2 and 4.07 × 10 -2 mA/cm 2 ), the V OC values (0.429 V and 0.426 V) and the fill factor value (FF = 0.66 %) compared with other organic and natural sensitizer were due to the better interaction between the carboxyl and carbonyl groups of aryl azo molecule attached to the thiazolyl nucleus and the surface of TiO 2 porous film.…”

Section: Photovoltaic Performance Of the Dsscsmentioning

confidence: 99%

Synthesis of Novel Arylazothiazolyl-thiophene Dyes for Solar Cell and Nonlinear Optical Materials

Khalifa

Al-Amoudi

Gobouri

et al. 2016

ACSi

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Synthesis and investigation of new donor-acceptor conjugated N-(5-arylazothiazol-2-yl)-2-aminothiophene derivativeswith the aim to elucidate the contribution of their interaction with solvent molecules upon intramolecular charge transfer for their potential solar cells application is reported. The UV-visible and emission spectra measurements indicated that the properties of the synthesized dyes had a significant effect on the visible absorption and emission maxima. The effect of the donor and acceptor groups were studied for the nonlinearity based on their HOMO-LUMO band gap energy. The dye-sensitized solar cells (DSSCs) were assembled by using the newly synthesized aryl thiazolyl-thiophene dyes as sensitizers. The promising results of J SC (2.46 × 10 -2 and 4.07 × 10 -2 mA/cm 2 ), the V OC (0.429 V and 0.426 V) and the FF (0.66 %) values obtained compared to other organic and natural sensitizer were due to the better interaction between the carboxyl and carbonyl groups of aryl azo molecule attached to the thiazolyl nucleus and the surface of TiO 2 porous film.

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“…1) and their optical and electrochemical properties comparing with in depth theoretical calculations. 15 We also demonstrate the influence of soaking time and co-adsorbate over the performance of the DSSCs.…”

Section: Introductionmentioning

confidence: 99%

Coplanar D-π-A organic sensitizers featuring a thienylethynyl spacer for efficient dye-sensitized solar cells

Park¹,

Ahn²,

Baek³

et al. 2017

mat express

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We simply synthesize coplanar metal-free organic sensitizers featuring a thienylethynyl spacer, CSD-01 and CSD-02, from commercially available thiophene derivatives. The dye-sensitized solar cells (DSSCs) based on the CSD-01 and CSD-02 without any coadsorbate show the power conversion efficiencies ( ) of 4.60% and 5.32%, respectively. The study in the dye-adsorption time suggests the increase in the organic DSSC performance with decreasing soaking time.

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Facile synthesis of metal-free organic dyes featuring a thienylethynyl spacer for dye sensitized solar cells

Cited by 43 publications

References 21 publications

Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells

Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells

Synthesis of Novel Arylazothiazolyl-thiophene Dyes for Solar Cell and Nonlinear Optical Materials

Coplanar D-π-A organic sensitizers featuring a thienylethynyl spacer for efficient dye-sensitized solar cells

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