A chromogenic and fluorogenic rhodol-based chemosensor for hydrazine detection and its application in live cell bioimaging

Mechanochemical Duff Reaction in Solid Phase for Easy Access to Mono- and Di-formyl Electron-Rich Arenes

“…To date, mechanochemistry is mostly limited to single-step chemical transformations, and tandem processes are scantily demonstrated . We envisaged that a mechanochemical tandem reaction is possible for the synthesis of a common commercial dye (e.g., a rhodol derivative) that involves TFA as the reaction media. , First, in a stepwise manner, 2-(4-(diethylamino)-2-hydroxybenzoyl)­benzoic acid ( 5a ) was synthesized via a Friedel–Craft reaction by milling 3-(diethylamino)­phenol ( 1q ) mixing with a stoichiometric amount of phthalic anhydride in the presence of 2 equiv of H 2 SO 4 and silica as the matrix in 96% yields within 1 h (Scheme ). Further, compound 5a was milled with resorcinol ( 1p ) for 2 h at 25 Hz to give the rhodol derivative ( 5b ) in an excellent yield (95%).…”

“…Notably, in a tandem process without isolating 5a , the same reaction afforded the rhodol derivative, 5b , in 88% without any significant drop in overall yield. However, the conventional synthesis of the dye using toluene and TFA as the media under refluxing conditions for long hours in a stepwise manner results in a lower yield of 55% for 5b over two-steps . In addition, the mechanochemical protocol is devoid of a work-up step.…”

Synthesis, characterization, and hydrazine sensing property of two covalent organic frameworks

“…However, after adding hydrazine to TAPB-DHE, hydrazine can react with the ester group in TAPB-DHE and convert the ester group into hydroxyl group. [28][29][30] Because the hydroxyl group is an electron-donor group, the ICT process from triphenylbenzene to hydroxyl group is inhibited, leading to a significant enhancement of the fluorescence. Compared with TAPB-DHE, TAPT-DHE has two groups, triazine and ester group, but both triazine and ester groups are electron-acceptor groups, and there is no ICT process from triazine to ester group.…”

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.…”