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Fluorescent Rotary Switches: Four- vs Three-Substituted Phthalimide Boron Difluoride Schiff Base Complexes
Dancho Yordanov1,2, Rastislav Smolka3, Kosuke Nakashima4
1Department of Organic Chemistry, University of Chemical Technology and Metallurgy, 8 St. Kliment Ohridski blvd, 1756 Sofia, Bulgaria.
Abstract:
The influence of the substitution pattern in phthalimide boron difluoride Schiff base complexes as fluorescent molecular rotors has been investigated. Due to their ground-state zwitterionic structures, they have exhibited negative solvatochromism in absorption and blue-green emission with moderate to satisfactory photoluminescence quantum yields in solution. Ground-state and excited-state theoretical calculations and time-resolved emission spectroscopy revealed that the excited-state rotation is triggered by planar-induced charge transfer, resulting in switched emission toward the green region. Fluorescence lifetime measurements and species-associated emission spectra exhibited two emitting excited species in equilibrium via a planar transition-state barrier. The substitution pattern models showed different behavior in solid-state mechanochromic switching and were analyzed by subcell unit packing obtained from X-ray structure data. We have attempted to gain in-depth insight into the fluorescence mechanism and photoluminescence properties associated with the substitution pattern of the phthalimide motif in order to understand the structure-property-function relationship.
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Colors and Magnetism
When atoms or molecules absorb light at the proper frequency, their electrons are excited to higher-energy orbitals. For many main group atoms and molecules, the absorbed photons are in the ultraviolet range of the electromagnetic spectrum, which cannot be detected by the human eye. For coordination compounds, the energy difference between the d orbitals often allows photons in the visible range to be absorbed and emitted, which is seen as colors by the human...