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Issue 12, 2017
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Novel intramolecular π–π-interaction in a BODIPY system by oxidation of a single selenium center: geometrical stamping and spectroscopic and spectrometric distinctions

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Abstract

A new BODIPY system displaying an intramolecular π–π-interaction was synthesized and studied. When the selenium center was oxidized, the substituted phenyl group undergoes π–π 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 Cs to C1. The compound was characterized by X-ray diffraction; DFT methods helped elucidate the influence of the unexpected π–π stack and its connection to the photophysical properties imparted by the Se oxidation.

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

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Publication details

The article was received on 14 Feb 2017, accepted on 02 Mar 2017, published on 02 Mar 2017 and first published online on 02 Mar 2017


Article type: Paper
DOI: 10.1039/C7DT00555E
Citation: Dalton Trans., 2017,46, 4111-4117
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    Novel intramolecular π–π-interaction in a BODIPY system by oxidation of a single selenium center: geometrical stamping and spectroscopic and spectrometric distinctions

    Y. Kim, T. Jun, S. V. Mulay, S. T. Manjare, J. Kwak, Y. Lee and D. G. Churchill, Dalton Trans., 2017, 46, 4111
    DOI: 10.1039/C7DT00555E

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