Novel intramolecular pi-pi-interaction in a BODIPY system by oxidation of a single selenium center: geometrical stamping and spectroscopic and spectrometric distinctions

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A new BODIPY system displaying an intramolecular pi-pi-interaction was synthesized and studied. When the selenium center was oxidized, the substituted phenyl group undergoes pi-pi stacking with one side of the BODIPY core. The oxidized form showed, not only a down-field shift in the NMR peak, but also splitting due to geometrical changes that arise when going from C-s to C-1. The compound was characterized by X-ray diffraction; DFT methods helped elucidate the influence of the unexpected pi-pi stack and its connection to the photophysical properties imparted by the Se oxidation.
Publisher
ROYAL SOC CHEMISTRY
Issue Date
2017-03
Language
English
Article Type
Article
Keywords

AGGREGATION-INDUCED EMISSION; LIVING CELLS; TURN-ON; FLUORESCENT-PROBES; CANCER-CELLS; ORGANOSELENIUM CHEMISTRY; HYPOCHLOROUS ACID; SOLVENT POLARITY; SE-BODIPY; TELLURIUM

Citation

DALTON TRANSACTIONS, v.46, no.12, pp.4111 - 4117

ISSN
1477-9226
DOI
10.1039/c7dt00555e
URI
http://hdl.handle.net/10203/223510
Appears in Collection
CH-Journal Papers(저널논문)
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