Hydrazinopyrimidine derived novel Al3+ chemosensor: molecular logic gate and biological applications. (10th May 2018)

• Record Type: Journal Article
• Authors: Das, Bhriguram; Dey, Satyajit; Maiti, Guru Prasad; Bhattacharjee, Ankita; Dhara, Anamika; Jana, Atanu
• Is Part Of: New journal of chemistry. Volume 42:Number 12(2018)
• Page Start: 9424
• Page End: 9435
• Publication Date: 2018-05-10
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c7nj05095j
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : For the first time, a hydrazinopyrimidine based chemosensor has been designed for sensing Al 3+ through CHEF-PET-ESIPT fluorescence mechanisms and by building an 'INHIBIT' molecular logic gate. Abstract : Cost-effective and highly sensitive biocompatible probes for the detection of Al 3+ have tremendously important practical applications. Herein, we report for the first time, the hydrazinopyrimidine based Al 3+ chemosensorL (1-[(4, 6-dimethyl-pyrimidin-2-yl)-hydrazonomethyl]-naphthalen-2-ol) prepared by the condensation of 2-hydroxy-1-naphthaldehyde and 4, 6-dimethyl-2-hydrazino-pyrimidine. Our as-synthesized chemosensorL ( Φ = 0.0066) shows ∼15 fold fluorescence enhancement in the presence of Al 3+ ( Φ = 0.0955, K a = 1.9 × 10 4 M −1 ) via chelation enhanced fluorescence (CHEF), excited state intramolecular proton transfer (ESIPT), and inhibited photo-induced electron transfer (PET) phenomena. The limit of detection (LOD) and limit of quantification (LOQ) were estimated to be 2.78 μM and 9.27 μM, respectively. Furthermore, for the first time, a hydrazino pyrimidine based 'INHIBIT' molecular logic gate for Al 3+ was successfully developed using the fluorescence properties ofL . The experimental sensing mechanisms ofL for Al 3+ were corroborated by theoretical calculations. Biocompatibility and good water-solubility properties of a pyrimidine moiety ofL inspired us to investigate Al 3+ imaging in human embryonic kidney cell lines, HEK293, and the results for practical applications are highly promising.