A new type of dioxetane bearing a 3-(cyanomethyl)phenyl (1a), 3-(methoxycarbonylmethyl)phenyl (1b), 3-(benzoylmethyl)phenyl (1c), or 3-[cyano(methoxycarbonyl)methyl]phenyl group (1d) decomposed through an intermediary dioxetane bearing a benzylic carbanion to afford crimson to yellow light on treatment with TBAF in DMSO.
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Food Chem
July 2024
Xiangya School of Pharmaceutical Sciences, Central South University, Changsha 410013, PR China; Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Changsha 410013, PR China. Electronic address:
Real-time optical sensing of mercury has been developed rapidly in recent years but remains challenging such as bearing background interference. Herein, a Hg and base dual-activatable ultrasensitive chemiluminescent probe CL-Hg based on benzothiazole-phenoxyl-dioxetane with profits of excitation light-free and minimal interference is presented. The photophysical properties study and sensing performance verified CL-Hg is coupled with unique advantages of long-term detection (more than 400 min), ultrahigh sensitivity (LOD = 0.
View Article and Find Full Text PDFRSC Chem Biol
August 2023
Department of Chemistry, Koç University, Rumelifeneri Yolu Istanbul 34450 Turkey
Hydrogen sulfide (HS) as a critical messenger molecule plays vital roles in regular cell function. However, abnormal levels of HS, especially mitochondrial HS, are directly correlated with the formation of pathological states including neurodegenerative diseases, cardiovascular disorders, and cancer. Thus, monitoring fluxes of mitochondrial HS concentrations both and with high selectivity and sensitivity is crucial.
View Article and Find Full Text PDFAnalyst
July 2023
School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai 201203, China.
By constructing 2-(benzoylthio)benzoate and a 2-fluoro-4-nitrobenzoate structure in an adamantylidene-dioxetane system, we designed and synthesized two novel chemiluminescent probes for the detection of HS from other RSS. Under the same conditions, the maximum luminescence emission intensity of the probe CL-HP2 could reach 150 times that of the probe CL-HP1, and the chemiluminescence signal still existed at low concentrations. Therefore, CL-HP2 was more suitable for HS detection as a chemiluminescent probe.
View Article and Find Full Text PDFOrg Lett
June 2023
Molecular Synthesis Center and Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China.
The triethylamine-promoted cascade Henry reaction/elimination of HNO/cyclization reaction of 2-oxoaldehydes with nitroalkanes bearing various remote functionalities is described. Both chiral and achiral nitroalkanes were applicable to this protocol, leading to a variety of oxacycles, such as chromenes, chromanes, cyclic hemiacetals, and polycyclic acetals. An unexpected regioselective photooxygenation occurred without sensitizer during derivatization to convert a derived diene product into a dioxetane by reaction with singlet oxygen, which provided chromen-2-one and benzaldehyde after fragmentation.
View Article and Find Full Text PDFJ Org Chem
January 2023
Department of Chemistry, Yeungnam University, Gyeongsan, Gyeongbuk 38541, Korea.
Photooxygenation reactions of electron-deficient enaminoesters bearing an oxophilic silyl tether at the α-position of the nitrogen atom using methylene blue (MB) were explored to develop a mild and efficient photochemical strategy for oxidative C-C double bond cleavage reactions via singlet oxygen (O). Photochemically generated O, through energy transfer from the triplet excited state of MB (MB*) to molecular oxygen (O), was added across a C-C double bond moiety of enaminoesters to form perepoxides, which rearranged to form dioxetane intermediates. The cycloreversion of the formed dioxetane via both C-C and O-O bond cleavage processes led to the formation of oxamates.
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