Luminescent Anion Sensing by Transition Metal Dipyridylbenzene Complexes Incorporated into Acyclic, Macrocyclic and Interlocked Hosts

Chemistry : a European Journal
Richard Charles KnightonPd D Beer

Abstract

A series of novel acyclic, macrocyclic and mechanically interlocked luminescent anion sensors have been prepared via incorporation of the isophthalamide motif into dipyridylbenzene to obtain cyclometallated complexes of platinum (II) and ruthenium (II). Both the acyclic and macrocyclic derivatives 7·Pt , 7·Ru·PF 6 , 10·Pt and 10·Ru·PF 6 are effective sensors for a range of halides and oxoanions. The near-infrared emitting ruthenium congeners exhibited an increased binding strength compared to platinum due to the cationic charge and thus additional electrostatic interactions. Intramolecular hydrogen-bonding between the dipyridylbenzene ligand and the amide carbonyls increases the preorganisation of both acyclic and macrocyclic metal derivatives resulting in no discernible macrocyclic effect. Interlocked analogues were also prepared, and preliminary luminescent chloride anion spectrometric titrations with 12·Ru·(PF 6 ) 2 demonstrate a marked increase in halide binding affinity due to the complementary chloride binding pocket of the [2]rotaxane. 1 H NMR binding titrations indicate the interlocked dicationic receptor is capable of chloride recognition even in competitive 30% aqueous mixtures.

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Citations

May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mauro FormicaEnrique García-España
Mar 6, 2021·Angewandte Chemie·Pachaiyappan RajamalliEli Zysman-Colman
May 14, 2021·Organic & Biomolecular Chemistry·Hui Min Tay, Paul Beer
Jun 11, 2021·Coordination Chemistry Reviews·Chenxing GuoJonathan L Sessler
Jul 29, 2021·Chemistry : a European Journal·Yuen Cheong TsePaul D Beer

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Methods Mentioned

BETA
size‐exclusion chromatography
X‐ray
NMR
column chromatography

Software Mentioned

WINEQNMR2
SPECFIT

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