Development of fluorophoric [2]pseudorotaxanes and [2]rotaxane: selective sensing of Zn(II).

Abstract

Fluorophoric [2]pseudorotaxanes {NiPR1(ClO4)2-NiPR3(ClO4)2} are synthesized by utilizing newly designed fluorophoric bidentate ligands (L1-L3) and a heteroditopic naphthalene containing macrocycle (NaphMC) with high yields via Ni(II) templation and π-π stacking interactions. Subsequently, a fluorophoric [2]rotaxane (NAPRTX) is established through a Cu(I) catalysed click reaction between an azide terminated pseudorotaxane, {NiPR4(ClO4)2}, which contains the newly designed fluorophoric ligand L4, and alkyne terminated bulky stopper units. All these fluorophoric [2]pseudorotaxanes and the [2]rotaxane were characterized using numerous techniques such as mass spectrometry, NMR, UV/Vis, PL, and elemental analysis, wherever applicable. Furthermore, to investigate the effect of the fluorophoric moieties, the coordinating ability of chelating units, and size and shape of the three dimensional cavity generated by the mechanical bond in the interlocked [2]rotaxane (NAPRTX), we have performed a sensing study of various metal ions. Thus, the interlocked [2]rotaxane is found to have potential as a selective fluorescent sensor for Zn(II) metal ions over other transition, alkali and alkaline earth metal ions, where the 2,2'-bipyridyl arylvinylene moiety of the axle acts as a fluorescence signalling unit.