Intramolecular pi-stacking interaction in a rigid molecular hinge substituted with 1-(pyrenylethynyl) units.

Synthesis of a tetrakis(1-pyrenylethynyl)-substituted rigid hinge-like molecule (1) is described. The intramolecular pi-stacking interaction of the pyrene units is studied by 1H NMR and fluorescence spectroscopy. Due to intramolecular pi-stacking interactions, chemical shifts of the pyrene protons in 1 are highly shielded in the NMR spectrum. Fluorescence from the static excimer state is observed due to pi-stacking interactions among the pyrene units in the ground state of 1. Based on the spectroscopic evidence, conformations and dynamics of 1, arising from the hindered rotation of the major axis, are proposed.