A Triphenyl Amine-Based Solvatofluorochromic Dye for the Selective and Ratiometric Sensing of OCl− in Human Blood Cells

• Published in: Chemistry, an Asian journal Vol. 10; no. 3; pp. 694 - 700
• Main Authors: Goswami, Shyamaprosad, Aich, Krishnendu, Das, Sangita, Pakhira, Bholanath, Ghoshal, Kakali, Quah, Ching Kheng, Bhattacharyya, Maitree, Fun, Hoong-Kun, Sarkar, Sabyasachi
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.03.2015; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: Amines - chemistry; Blood; blood-cell imaging; Chemistry; Crystallography; Erythrocytes - chemistry; Fluorescent Dyes - chemistry; fluorescent probes; Humans; hypochlorite; Hypochlorous Acid - chemistry; Models, Molecular; Molecular Structure; ratiometric; sensors; solvatofluorochromism; ratiometric; hypochlorite; sensors; solvatofluorochromism; fluorescent probes; blood-cell imaging
• ISSN: 1861-4728; 1861-471X; 1861-471X
• DOI: 10.1002/asia.201403234

A new visible‐light‐excitable fluorescence ratiometric probe for OCl− has been developed based on a triphenylamine‐diamiomaleonitrile (TAM) moiety. The structure of the dye was confirmed by single‐crystal X‐ray analysis. It behaves as a highly selective and sensitive probe for OCl− over other analytes with a fast response time (∼100 s). OCl− reacts with the probe leading to the formation of the corresponding aldehyde in a mixed‐aqueous system. The detection limit of the probe is in the 10−8 M range. The probe (TAM) also exhibits solvatofluorochromism. Changing the solvent from non‐polar to polar, the emission band of TAM largely red‐shifted. Moreover, the probe shows an excellent performance in real‐life application in detecting OCl− in human blood cells. The experimentally observed changes in the structure and electronic properties of the probe after reaction with OCl− were studied by DFT and TDDFT computational calculations. Green means danger! A new triphenyl amine‐diaminomaleonitrile‐based probe was synthesized. This probe acts as a polarity probe with a strong positive emission solvatofluorochromism. It exclusively detects OCl− in a ratiometric manner in a mixed aqueous system with a detection limit of about 10−8 M. Moreover, it can detect OCl− in vivo in human blood cells.