A fluorene based probe: Synthesis and “turn-on” water sensitivity of the in-situ formed Cu2+ complex: Application in bio-imaging

Abstract

A new fluorene based probe (FTH) has been evaluated for its photo-physical properties in solution as well as in the aggregated state/viscous environment. Addition of a poor solvent (water) to the solution of the probe in a good (acetonitrile) solvent significantly enhanced the otherwise weak emission due to aggregation induced emission (AIE). The emission enhancement is also related to the increase in viscosity of the solution, leading to the restricted intramolecular rotation of the peripheral (phenyl) groups. Interestingly, the emission behaviour of the non-emissive in-situ formed Cu2+ complex is drastically modulated in the presence of water. The solution of the putative Cu2+ complex of the probe turns highly emissive (yellow colour) upon addition of a small fraction of water (up to 7.6 wt %), but the yellow emission diminishes upon increasing higher water fraction. We propose that the initially formed Cu2+ complex undergoes hydrolysis in the presence of higher water content releasing the free amine possessing the diaryl amino rotors thus rendering the solution non-emissive. Thus the current probe being reported herein discloses its potential to generate trace water sensitive turn-on Cu2+ complex. Additionally, the bio-imaging potential of FTH for live cancer cells and its sensitivity towards intracellular presence of Cu2+ ions has been demonstrated. © 2021 Elsevier B.V.