Dithienothiophene (DTT)-based dyes for dye-sensitized solar cells: synthesis of 2,6-dibromo-DTT.

School of Chemistry, Bio21 Institute, University of Melbourne , Parkville, Vic 3010, Australia.
The Journal of Organic Chemistry (Impact Factor: 4.56). 05/2011; 76(10):4088-93. DOI: 10.1021/jo2001484
Source: PubMed

ABSTRACT A one-pot synthesis of 2,6-dibromodithieno[3,2-b;2',3'-d]thiophene (dibromo-DTT, 4) was developed. A key step was bromodecarboxylation of DTT-2,6-dicarboxylic acid, obtained by saponification of the diester 1. The donor-acceptor dye DAHTDTT (13), based on a central 2,6-bis[2'-(3'-hexylthienyl)]dithieno[3,2-b;2',3'-d]thiophene core (9), was prepared and incorporated in a dye-sensitized solar cell (DSC), which exhibited an energy conversion efficiency of 7.3% with V(oc) of 697 mV, J(sc) of 14.4 mA/cm(2), and ff of 0.73 at 1 sun.

  • [Show abstract] [Hide abstract]
    ABSTRACT: We have synthesized and characterized four organic dyes (H1-H4) based on a 3,6-disubstituted carbazole donor as sensitizers in dye-sensitized solar cells. These dyes have high molar extinction coefficients and energy levels suitable for electron transfer from an electrolyte to nanocrystalline TiO(2) particles. Under standard air mass 1.5 global (AM 1.5 G) solar irradiation, a device using dye H4 exhibits a short-circuit current density (J(sc)) of 13.7 mA cm(-2), an open-circuit voltage (V(oc)) of 0.68 V, a fill factor (FF) of 0.70, and a calculated efficiency of 6.52%. This performance is comparable to that of a reference cell based on N719 (7.30%) under the same conditions. After 1000 hours of visible-light soaking at 60 °C, the overall efficiency remained at 95% of the initial value.
    Chemistry - An Asian Journal 12/2011; 7(2):343-50. · 4.57 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: Two new carbazole-based organic dye sensitizers are designed and investigated in silico. These dyes are designed through chemical modifications of the π-conjugated bridge of a reference organic sensitizer known as Carbz-PAHTDDT (S9) dye. The aim of designing these dyes was to reduce the energy gap between their highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) and to red-shift their absorption response compared to those of the reference S9 dye sensitizer. This reference dye has a reported promising efficiency when coupled with ferrocene-based electrolyte composition. To investigate geometric and electronic structure, density functional theory (DFT) and timedependent DFT (TD-DFT) calculations were conducted on the new dyes as well as the reference dye. The present study indicated that the long-range correction to the theoretical model in the TD-DFT simulation is important to produce accurate absorption wavelengths. The theoretical studies have shown a reduced HOMO-LUMO gap and red-shifted absorption spectra for both of the new candidate dyes. In particular, the new S9-D1 dye is found to have significant reduced HOMO–LUMO energy gap, greater push–pull character and higher wavelengths of absorption when compared to the reference dye. Such findings suggest that the new dyes are promising and suitable for optoelectronic applications.
    Journal of Molecular Modeling 03/2014; 20(3). · 1.98 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: The critical review on the recent development of novel narrow bandgap polymers for high-efficiency polymer solar cells concentrates on (i) the structural design of narrow bandgap polymers, which occupy a central place in recent advances in high-efficiency polymer solar cells, (ii) the intrinsic physics and chemistry of special properties, such as absorption, bandgap and energy levels, and (iii) the correlation of polymer structure and device fabrication with their photovoltaic performances. The statistical summaries of their device parameters are also discussed. The description of these structure–property correlations may guide the rational design of polymer structures and the reasonable evaluation of their photovoltaic performance.
    Progress in Polymer Science. 09/2012; 37(9):1292–1331.


1 Download
Available from
Oct 1, 2014
Available from