A highly sensitive fluorescent probe for ozone based on coumarin-benzothiazole derivative

Abstract

Ozone is widely used in daily life, but studies have shown that O3 can damage human trachea and lungs, leading to diseases such as asthma, emphysema, and bronchitis. Therefore, it is of great significance to develop a simple and efficient detection method for monitoring O3 in living cells. In this study, 3-(but-3-en-1-yl)-2-(7-(but-3-en-1-yloxy)-2-oxo-2H-chromen-3-yl)benzo[d]thiazol-3-ium (BCT) as a new type of water-soluble fluorescent probe was synthesized by substitution reaction of 4-bromo-1-butene and hydroxycoumarin-benzothiazole derivatives, which can specifically detect ozone in aqueous solution. The interaction of ozone on the probe can be completed within 20 min, the fluorescence intensity is significantly enhanced, and it has the advantages of high sensitivity (detection limit LOD = 43 nM). The influence of pH on the fluorescent performance of BCT shows that the probe with super stability under weak alkali and acidic environment, which provides the necessary conditions for its detection of ozone in physiological system detection. Therefore, BCT is expected to become an effective tool for detecting ozone in cellular organisms.

A minireview of recent developments in ozone detection using optical chemodosimeters

“…Recently, chemodosimeter 9 based on a coumarin-benzothiazole derivative for selective sensing of ozone has been devised by Chen et al 58 The free OH group and N atoms were blocked by 4-bromo-1-butene in chemodosimeter 9 , resulting in a faint fluorescence. When the chemodosimeter reacted with ozone in a PBS buffer solution, the protecting groups were destroyed and product 9a was formed, resulting in a rise in fluorescence at 550 nm ( λ ex = 425 nm) that peaked in 20 minutes.…”

One-pot, simple, and facile synthesis of 4-(3-benzylbenzo[d]thiazol-2(3H)-ylidene)-cyclohexa-2,5-dien-1-one derivatives via a novel three-component reaction

“…7,8 Derivatives of benzothiazole have been reported to show a wide spectrum of pharmacological activities and agrochemical applications like anti-convulsant, 9 antiallergy, 10 antifungal, 10 anti-microbial, 11 anti-oxidant, 12 anti-inflammatory, 12 anti-diabetic, 13 neuroprotective, and many others 14 (Figure 1). On the other hand, benzothiazoles are also widely used in a variety of consumer and industrial products such as nonlinear optics (NLOs), organic light-emitting diodes (OLEDs), fluorescent probes, luminescence, chemosensors, 15–17 and liquid crystals. 18 In this paper, the results of studies involving new, easy, and catalyst-free multicomponent reactions of 2-chlorobenzothiazole ( 1) , benzyl bromides ( 2) , and phenols ( 3) for the preparation of 4-(3-benzylbenzo[ d ]thiazol-2(3 H )-ylidene)-cyclohexa-2,5-dien-1-one derivatives 4a–i are reported (Scheme 1 and Scheme 2).…”