Connecting Direct C-H Arylation Reactions with Dye-Sensitized Solar Cells: A Shortcut to D-A-π-A Organic Dyes.

A step-economical synthetic strategy is developed to target thieno[3,4-c]pyrrole-4,6-dione (TPD)-based D-A-π-A organic dyes for dye-sensitized solar cells (DSSCs). Through sequential Pd-catalyzed direct C-H (hetero)arylation reaction, synthesis of the push-pull-type small molecules is reduced from the traditional six steps to two steps. In this report, we focus on the optimization of the key C-H monoarylation of TPD by screening ligands, acid additives, bases, and solvents. The reaction proves versatile toward new D-A-π-A organic dyes with a variety of different donor groups, and several derivatives are efficiently prepared under optimum reaction conditions. The sensitive aldehyde functionality that is a required intermediate for conversion into anchoring groups for TiO2 is well tolerated. Based on our synthetic study, DSSCs are fabricated and characterized using two designed sensitizers. The photovoltaic characterization of the devices affords an open-circuit voltage of 0.60-0.69 V, a short-circuit current density of 10.85-11.07 mA cm(-2), and a fill factor of 69.9-70.8 %, which corresponds to an overall power conversion efficiency of 4.61-5.33 %.