Dithienothiophene (DTT)-Based Dyes for Dye-Sensitized Solar Cells: Synthesis of 2,6-Dibromo-DTT

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.

D–A copolymer with high ambipolar mobilities based on dithienothiophene and diketopyrrolopyrrole for polymer solar cells and organic field-effect transistors

“…We synthesized 2,6-bis(tri-n-butylstannyl) dithieno [3,2- [44][45][46] and 3,6-bis(5-bromothien-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo [3,4-c]pyrrole-1,4(2H,5H)-dione (2) [47] according to the previously published literature. All air-and water-sensitive reactions were performed under a nitrogen atmosphere.…”

Fused-Thiophene Based Materials for Organic Photovoltaics and Dye-Sensitized Solar Cells

“…In addition, Bach et al developed sensitizer 60 based on a 2,6-bis[2-(3-hexylthienyl)]dithieno [3,2-b;2,3-d]thiophene core as the π-spacer [54]. Structural modification through an additional double bond and 3-hexylthiophene in the spacer caused it to exhibit a broad absorption spectrum and inhibited the electron recombination from the TiO2 nanoparticle to the radical cation of the dye, due to the presence of the hexyl substituents.…”

Characterization of photo-induced electron and hole transfer in a porphyrin based ambipolar organic molecule with cascade energy levels

“…An efficiency up to 13.0% has been shown recently with a D-A structured diphenylamine modified porphyrin dye in dye-sensitized solar cells (DSSC) by Gr€ atzel and coworkers [14]. As the electronic donor, metalloporphyrins have lower oxidation potentials than those of the corresponding metalfree porphyrins, which are used extensively in photo-induced electron transfer of organic solar cells or DSSC and obtained high efficiency (>10%) [19e25].…”