Dithienothiophene (DTT)-Based Dyes for Dye-Sensitized Solar Cells: Synthesis of 2,6-Dibromo-DTT
Tae-Hyuk Kwon, Vanessa Armel, Andrew Nattestad, Douglas R MacFarlane, Udo Bach, Samuel J Lind, Keith C Gordon, Weihua Tang, David J Jones, Andrew B Holmes
Journal of Organic Chemistry | AMER CHEMICAL SOC | Published : 2011
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.
Awarded by Australian Government
We thank the Australian Research Council, the Australian Government [DIISR ISL (CG10059)], and the Victorian State Government DPI (SERD) and DBI (VSA SPF) Program VICOSC for financial support. We thank Drs. Joseph Frey and Michael Armitage (University of Cambridge) for their early observations on the bromodecarboxylation reactions of DTT-carboxylic acids.