Chiral Diazatriptycene Exhibiting Acid‐Induced Ternary Circularly Polarized Luminescence Switching and Crystal Morphology Changes

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Doubly N ‐doped triptycene 2,6‐diazatriptycene 1 was synthesized as the first example of triptycene‐bearing intrinsic chirality in its core. The resolved enantiomers exhibited an acid‐induced ternary circularly polarized luminescence (CPL) switching behavior, enabling on/off and +/− control, with a dissymmetry factor ( g lum ) of approximately 10 −3 . Density functional theory calculations indicated that these ternary CPL changes were derived from modulation of through‐space conjugation within the triptycene skeleton. In addition, single‐crystal X‐ray analysis of 1 and the salt 1 •(TfOH) n revealed the presence of herringbone arrangements, trimer clusters, chiral porous tubes, and 2D charge‐segregated array structures. These results demonstrate that precise change of the molecular assembly can be achieved using N ‐doped chiral triptycene facilitated by ionic hydrogen bonding and donor‐acceptor π‐π stacking.