Journal of Organic Chemistry 2011-05-20

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

Index: J. Org. Chem. 10th ed., 76 , 4088-4093, (2011)

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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.