Z-Axis-Oriented Pyrene Architectures: Regioselective Bipolar Engineering for Full Color-Tunable Emission

Controllably functionalizing pyrene at specific active sites along the Z-axis remains a significant synthetic challenge. In this work, we present a rationally designed synthetic strategy for the stepwise Z-axis functionalization of pyrene at the 1,3- and 6,8-positions, using a hydroxyl group at the 2-position as a directing group. This approach allows for the construction of novel Z-axis-oriented bipolar pyrene-based molecules. By modulating electron-withdrawing or -donating groups at the 6- and 8-positions, the products demonstrated tunable luminescence ranging from deep blue (426 nm) to orange red (627 nm) with a high fluorescence quantum efficiency.