A domino sequence, involving a phosphinoauration and a gold-catalyzed 6-endo-dig cyclization step, was developed. Starting from modular and simple-to-prepare phosphadiynes, π-extended phosphoniumfluorenes were synthesized. The mechanistic proposal was supported by kinetic measurements and by the trapping of key intermediates. These led to important conclusions for the gold-catalyzed hydroarylation mechanism. Cyclic voltammetry (CV) and UV/Vis spectroscopy measurements indicated interesting properties for materials science. The phosphoniumfluorene structure was tested as a hole-blocking layer in perovskite solar cells of inverted architecture. Devices with the phosphoniumfluorene exhibited an efficiency of 14.2 %, which was much higher than that of devices without (10.7 %).
Keywords: cyclization; domino reactions; gold; hole-blocking layer; solar cells.
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