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On/off fluorescence emission induced by encapsulation, exchange and reversible encapsulation of a BODIPY-guest in self-assembled organometallic cages

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Abstract

A dynamic guest-binding study of BODIPY-derivative 3 (3 = 1,3,5,7,8-pentamethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) with two Cp*RhIII-based organometallic cages [Cp*6Rh6(μ-CA)3(tpt)2](OTf)6 1 (H2CA = chloranilic acid, tpt = 2,4,6-tripyridyl-1,3,5-triazine) and [Cp*6Rh6(μ-DHNA)3(tpt)2](OTf)6 2 (H2DHNA = 6,11-dihydroxynaphthacene-5,12-dione) have been demonstrated. While guest 3 displays a strong green fluorescence emission, the host–guest complexes 31 and 32 exhibit almost no emission. However, fluorescence emission can be again ‘turned on’ by adding coronene (4) or pyrene (5) into the solution of 31 and 32. Guests 4 and 5 show stronger binding affinities toward the organometallic cages 1 and 2 due to the strong electrostatic interactions between the electron-rich guest and electron-deficient tpt resulting in the displacement of 3 by 4 or 5, which eventually helps the fluorescence enhancement. Further guest-binding studies using a Job's plot experiment illustrate the formation of discrete 1 : 1 host–guest complexes which are also supported by 1H NMR spectroscopy and ESI mass spectrometry. The anion-exchange study with sodium chloride reveals that the chloride ion can effectively disassemble the host frameworks of 1 and 2 releasing the fluorescent guest 3 which can be again encapsulated into the cavity of reassembled cages promoted by the addition of silver triflate.

Graphical abstract: On/off fluorescence emission induced by encapsulation, exchange and reversible encapsulation of a BODIPY-guest in self-assembled organometallic cages

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Publication details

The article was received on 24 Dec 2018, accepted on 21 Jan 2019 and first published on 22 Jan 2019


Article type: Paper
DOI: 10.1039/C8DT05103H
Citation: Dalton Trans., 2019, Advance Article

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    On/off fluorescence emission induced by encapsulation, exchange and reversible encapsulation of a BODIPY-guest in self-assembled organometallic cages

    X. Gou, J. Peng, R. Das, Y. Wang and Y. Han, Dalton Trans., 2019, Advance Article , DOI: 10.1039/C8DT05103H

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