Near-Infrared-Emitting Probes for Detection of Nanomolar Hydrazine in a Complete Aqueous Medium with Real-Time Application in Bioimaging and Vapor-Phase Hydrazine Detection

Abstract

Hydrazine is a highly reactive inorganic compound that is commonly used as a thruster propellant in rocket fuels. In this report, the synthesis of a naphthofluorescein-based simple, sensitive, and selective colorimetric and fluorescent probe for the qualitative and quantitative determination of hydrazine is described. An ultrasensitive NIR probe is employed for the nanomolar detection of hydrazine with real-time applicability. The probe is capable of detecting hydrazine in a completely aqueous medium without the interference of other analytes. The probe reacts selectively with hydrazine and exhibits turn-on NIR emission with quantum yields ranging from Φ = 0.0011 to Φ = 0.5338. This enables the probe to selectively detect extremely low concentrations of hydrazine (∼47 nM). As a consequence, practical utility of the probe is greatly augmented. Eco-friendly test strips were prepared to monitor the hydrazine under aqueous and vapor phases. The potential of the probe was verified by monitoring the presence of hydrazine in a living system by fluorescence bioimaging studies of living cells.

Monitoring isoniazid metabolism in vivo using a near-infrared fluorescent probe

“…Hydrazine, as a synthetic intermediate, exists in some important drugs, such as carbidopa, isoniazid, and azilide hydrochloride. [1][2][3][4] The drug isoniazid, one of the four rst-line drugs used to treat tuberculosis, produces hydrazine during its metabolic process in vivo. [5][6][7] Nevertheless, hydrazine was further oxidized to reactive metabolites and involved in isoniazid hepatotoxicity, which was proposed to be mediated by microsomal P450s, especially CYP2E.…”

Phthalimide conjugation turns the AIE-active tetraphenylethylene unit non-emissive: its use in turn-on sensing of hydrazine in solution and the solid- and vapour-phase

“…Fluorimetric sensing, which involves interacting analyte with compatible organic molecules, offers crucial advantages such as high sensitivity, selectivity and cost-effectiveness, and has attracted many researchers in recent times. 15,16 A good number of chemosensors have been developed for uorimetric detection of hydrazine [17][18][19] based on well-known conventional dye molecules such as rhodols, 20 uorescein, 21 BODIPY, 22 dansyl, 23 resorun, 24 coumarin, [25][26][27] and many others. [28][29][30][31][32][33] In most of these reported methods, hydrazine has been assayed by evaluating the intensity changes in the uorescence output of the probe molecule by varying the concentration of the analyte in solution phase by the use of a uorimeter.…”

Diethyl Malonate-Based Turn-On Chemical Probe for Detecting Hydrazine and Its Bio-Imaging and Environmental Applications With Large Stokes Shift

“…During the last few decades, a series of turn-on probes were applied to detect N 2 H 4 in living biosamples (Cui et al, 2014 ; Goswami et al, 2014a , b , 2015 ; Liu et al, 2014 , 2019 ; Qian et al, 2014 ; Qu et al, 2014 ; Raju et al, 2014 ; Sun et al, 2014 , 2015 ; Xiao et al, 2014 ; Jin et al, 2015 ; Nandi et al, 2015 ; Yu et al, 2015 ; Zhang et al, 2015 ; Zhou J. et al, 2015 ; Dai et al, 2016 ; Reja et al, 2016 ; Chen et al, 2017 ; Li et al, 2017 , 2018 , 2019 ; Ma et al, 2017 ; Mahapatra et al, 2017 ; Jung et al, 2019 ; Paul et al, 2019 ; Shi et al, 2019 ; Xing et al, 2019 ; Fang et al, 2020 ; Han et al, 2020 ; Hou et al, 2020 ; Vijay and Velmathi, 2020 ), a few of which were constructed by cleavage of C = C bond (Sun et al, 2014 ; Reja et al, 2016 ; Li et al, 2017 , 2018 , 2019 ; Liu et al, 2019 ; Hou et al, 2020 ). Many examples were developed by the deprotection group from the fluorescent group (Cui et al, 2014 ; Goswami et al, 2014a , 2015 ; Liu et al, 2014 ; Qian et al, 2014 ; Qu et al, 2014 ; Raju et al, 2014 ; Jin et al, 2015 ; Sun et al, 2015 ; Yu et al, 2015 ; Zhang et al, 2015 ; Zhou J. et al, 2015 ; Chen et al, 2017 ; Ma et al, 2017 ; Mahapatra et al, 2017 ; Shi et al, 2019 ; Xing et al, 2019 ; Fang et al, 2020 ; Vijay and Velmathi, …”