Multi-Directional Mechanofluorochromism of Acetyl Pyrenes and Pyrenyl Ynones

A series of acetyl pyrenes and pyrenyl ynones with and without tert-butyl groups showed distinct mechanofluorochromism (MFC). Four pairs of polymorphic solids were found out of six compounds and interestingly, each of them showed hypsochromic, bathochromic or off-to-on MFC. The MFC properties were rationalized by categorizing the packing schemes into herringbone, sandwich, beta and gamma motifs depending on the relative contributions of C⋅⋅⋅C (or π-π) against C⋅⋅⋅H contacts. The bulky tert-butyl and trimethylsilyl groups served not only to reduce the number of aggregation patterns but also to prohibit the complete back reactions in solid state. Our results suggest that the simple pyrene derivatives may be promising candidates for a novel group of mechanically-sensitive materials.