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Mechanofluorochromic Anthryl Phosphonate/Benzoic Acid Cocrystals with a Large Blue Shift: The Role of P=O⋅⋅⋅H Interactions
Author(s) -
Prusti Banchhanidhi,
Chakravarty Manab
Publication year - 2020
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202000689
Subject(s) - cocrystal , benzoic acid , crystallography , blueshift , non covalent interactions , chemistry , materials science , crystal engineering , molecule , hydrogen bond , crystal structure , supramolecular chemistry , organic chemistry , optoelectronics , photoluminescence
Organophosphonates have a rich and diverse chemistry, but their mechanofluorochromic features have rarely been documented. Herein, we report on cocrystals of anthranylphosphonate with (E)‐4‐(2‐(anthracen‐9‐yl)vinyl)benzoic acid that exhibit reversible mechanofluorochromic properties with large blue shifts. Anisotropic grinding (or pressure of just 25 kPa) maintains the co‐crystals emission features but leads to a pronounced 59 nm (2087 cm −1 ) blue‐shift. Such an impressive blue‐shift for a cocrystal has not been reported to date. The underlying causes for the blue‐shift were validated by X‐ray diffraction (powder and single crystal) studies and Hirshfeld surface analysis. Twisted molecular conformations and P=O⋅⋅⋅ H/C=O⋅⋅⋅H/C⋅⋅⋅H noncovalent interactions afford molecular arrangements via slip‐stacks with two different pitch angles and relatively larger interlayer distances. The new compound was established as a potential medium for optical recording and security display.