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: 4.72). 05/2011; 76(10):4088-93. DOI: 10.1021/jo2001484
Source: PubMed


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.

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Available from: David John Jones, Oct 01, 2014
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    • "A common design rule for the small molecule donor material is connecting central building blocks and terminal electron withdrawing units with an oligothiophene linker232425262728. Based on our previous work29, dithieno[3,2-b;2′,3′-d]thiophene (DTT) was used as the central building block and 3′,3″-dihexyl-2,2′:5′,2″-tertthiophene13 was used as the linkage. Octyl cyanoacetate and octyl cyanoacetamide served as electron withdrawing groups to end cap the small molecules (Figure 1). "
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    ABSTRACT: Small molecules with dithieno[3,2-b;2',3'-d]thiophene as central building block and octyl cyanoacetate and octyl cyanoacetamide as different terminal building blocks have been designed and synthesized. The amide containing small molecule can form intermolecular hydrogen bonding between N-H…O = C of the amide group. The photovoltaic properties and active layer morphologies of the two molecules in bulk heterojunction solar cells are compared to study the influence of hydrogen bonding on the active layer morphology. New methanofullerene compound containing amide group has also been synthesized and compared with conventional fullerene electron acceptors.
    Scientific Reports 07/2014; 4:5701. DOI:10.1038/srep05701 · 5.58 Impact Factor
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    • "The optimization of this component has resulted in the development of new compounds to improve the absorption, morphology and stability. Ruthenium [5], triarylamines [6], squarines [7], thiophenes [8] [9], porphyrins [10] [11] and π-extended tetrathiafulvalenes (exTTFs) [12] have been incorporated and tested with promising results. In the past decades, there has been a growing interest in finding new sensitizers that are easy to prepare, exhibit high efficiency in solar energy conversion and can be prepared from easily available materials in order to avoid the high cost of the most efficient dyes, which contain ruthenium(II) [13]. "
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    ABSTRACT: Four new organic dyes, 1-4, containing triphenylamine (TPA) donors connected through different acetylene linkages to fluorene bridges and cyanoacrylic acid acceptors were designed and synthetized for photoconversion in dye sensitized solar cells (DSSCs). Their absorption spectra, electrochemical and photovoltaic properties were investigated. Shortening the bridge between the TPA moiety and the anchoring group leads to a dramatic increase in the overall photoconversion efficiency (1 > 3 > 4 > 2).
    Solar Energy Materials and Solar Cells 02/2014; 121:61–68. DOI:10.1016/j.solmat.2013.10.035 · 5.34 Impact Factor
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    • "A slight tilt from planarity in the conjugation bridge has been found to be beneficial for charge collection despite displaying blueshifted absorption [22]. Various conjugated segments such as carbazole [23] [24], fluorene [25e27], spirobifluorene [28], phenoxazine [29], oligothiophene [30], dithienothiophene [31], and thienothiophene [32] have been used as the p-bridge between the electron donor and electron acceptor for tuning the absorption parameters and photovoltaic performance. Incorporation of an acetylene segment is an interesting approach to increase the pconjugation in dyes that provide enhanced photovoltaic properties and ensure an efficient intramolecular charge separation with high photocurrent generation and slow recombination [33]. "
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    ABSTRACT: New organic dyes based on diphenylaminofluorene donors, cyanoacrylic acid acceptors and either ethynylbenzene or ethynylthiophene π-spacers have been synthesized and characterized as sensitizers for dye-sensitized solar cells. The dye with thiophene in the conjugation pathway exhibited longer wavelength absorption due to the significant lowering of the LUMO level when compared to the phenyl analog. However, the dye with the phenylacetylene linker displayed promising DSSC characteristics such as short circuit current, open circuit voltage and fill factor indicative of efficient charge generation and injection. The solvatochromic behavior of the dyes were examined in solvents of different polarity and found to exhibit negative solvatochromism of the fluorescence emission suggestive of a nonpolar solvent stabilized excited state with a significant structural reorganization. The TDDFT computations were used to explain the optical properties of the dyes.
    Dyes and Pigments 12/2012; 95(3):523-533. DOI:10.1016/j.dyepig.2012.06.004 · 3.97 Impact Factor
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