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Tuning Solid‐State Emission Behavior of Janus‐Type Anthracenes by Addition of Shielding Bridges

Von Wiley-VCH zur Verfügung gestellt

Janus-type anthracenes were synthesized to tune their luminescence behavior in the solid state. One face is free from steric hindrance, which allows for π-π stacking. The other face was shielded with joint-clip-shaped straps. The small and large clips recognized the edges of anthracene and themselves in the crystal, leading to green and blue luminescence, respectively. Anthracenes with moderate clips exhibited mechanofluorochromism.


Traditional π-face shielding is a useful technique to prepare emissive organic crystals. In this study, clip-shaped ether bridges with silicon spacers were introduced into Janus-type anthracenes with one shielded and one free π-face to tune emission behavior systematically. Single-crystal X-ray structure analysis and emission spectra revealed that packing structures, emission color, and responsivity to stimuli depended on the size of the bridges. Anthracene molecules with short bridges resulted in clip-anthracene and π-π interactions between anthracene rings, leading to green emission in the solid state. In contrast, anthracenes with long bridges resulted in clip-clip interactions without π-π interactions, resulting in blue emission in the solid state. Hirshfeld surface analysis revealed that anthracenes with moderate bridges resulted in weak clip-clip interactions in the crystal structure, which displayed mechanofluorochromism from blue to green emission.

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