In this work, with the aim of developing effective molecular probes and investigating the structure–reactivity correlation, a short series of phenothiazine‐based fluorescent probes are designed for the detection of ClO− with differing electron push‐pull groups. Sensing experiment results and single‐crystal X‐ray analysis with the aid of time‐dependent DFT (TD‐DFT) calculations reveal that substituting groups with increasing electron‐withdrawing ability can increase the dihedral angle of the phenothiazine moiety and reduce the gap energy of the probes, leading to enhanced reactivity toward ClO−. Both PT1 and PT2 show two‐color switching upon detection of ClO−. PT1, with the strong electron‐donating group thiophene, shows a fluorescence color switch from salmon to blue. PT2, with a medium electron‐donating/accepting group benzothiazole, shows a fluorescence color switch from red to green. However, both PT1 and PT2 show almost no response to ONOO−. Through the introduction of strong electron‐withdrawing ketone combined with a cyano group, PT3 shows a cyan emission upon detection of ClO− and weak red emission upon detection of ONOO−. HRMS and 1H NMR results confirm that PT1 and PT2 have the same sensing mode, in which the divalent sulfur of phenothiazine can be oxidized to sulfoxide by ClO−. Upon reaction with ClO−, PT3 experiences two‐step reactions. It is first oxidized into the sulfone structure by ClO−, and then transformed into sulfoxide phenothiazine aldehyde. Upon encountering ONOO−, PT3 changes into an aldehyde structure and some nonfluorescent byproducts. Owing to their special selectivity and high sensitivity, PT1 and PT2 are applied to image the endogenous ClO− in macrophage cells and zebrafish larvae. This study is expected to provide useful guidelines for probe design for various applications.
Chemistry - A European Journal – Wiley
Published: Jan 7, 2018
Keywords: ; ; ; ;
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