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

Abstract

A new AIE-based fluorimetric probe (TPE-PMI) has been successfully developed utilizing Gabriel reaction for the selective detection of hydrazine in solid, liquid and vapour phases.

Mechanochemical Synthesis of Organic Dyes and Fluorophores

“…Since the invention of aggregation-induced emission-active silole molecules by Tang’s group in 2001, this field has been the focus of extensive research in the last two decades . However, there are only limited attempts of to make AIEgens using mechanochemistry. , …”

“…51 However, there are only limited attempts of to make AIEgens using mechanochemistry. 52,53 Very recently, Hiremath et al reported the mechanochemical synthesis of a tetraphenylethylene (TPE)-based probe for the selective detection of hydrazine (Figure 6). 52 In a solvent-free approach, TPE-NH 2 (54) was condensed with phthalic anhydride in a mixer mill (MM400) in SS jar for 1 h at 30 Hz followed by heating in a sand bath for 2 h at 230 °C to afford the probe (55) in excellent yield (94%).…”

“…52,53 Very recently, Hiremath et al reported the mechanochemical synthesis of a tetraphenylethylene (TPE)-based probe for the selective detection of hydrazine (Figure 6). 52 In a solvent-free approach, TPE-NH 2 (54) was condensed with phthalic anhydride in a mixer mill (MM400) in SS jar for 1 h at 30 Hz followed by heating in a sand bath for 2 h at 230 °C to afford the probe (55) in excellent yield (94%). Probe 55 exhibits a fluorescence turn-on response upon interaction with hydrazine by cleavage of an imide moiety in a typical "Gabriel synthesis" pathway to release AIE-active 54 and phthalhydrazide as the side product (Figure 6A,B).…”

A fluorescent probe for the detection of N2H4 in solution, steam, and the biological system

“…40 Currently, the development of fluorescent probes with high sensitivity, high selectivity, and low toxicity for N 2 H 4 recognition remains challenging. 41–44…”

A new ratiometric switch “two-way” detects hydrazine and hypochlorite via a “dye-release” mechanism with a PBMC bioimaging study

“…12 Such oxidative stress can lead to a variety of diseases involving DNA mutations, aberrant electron transport, disruption of calcium homeostasis, activation of apoptosis, cardiovascular diseases, neuron degeneration, arthritis, and cancer. 13 Several studies have been reported so far by researchers based on the adverse impact of both hydrazine and hypochlorite towards flora and fauna, [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33] albeit there is significant room for improvement.…”