Design And Synthesis Of Fluorescent Probe For POh₃ And Biothiols Based On BODIPY

Triphenylphosphine, an important organic substance with a lone pair of electrons on phosphine, is a strong Lewis base and easy to form complexes with transition metals. In the chemical bonding in transition metal and phosphine generated. Therefore, PPh3 is ubiquitous for its nucleophilicity and reducing character. It is widely used in the synthesis of organic and organometallic compounds, such as Wittig reaction, Mitsunobu reaction, Mukaiyama-Corey lactonization, Appel reaction, Staudinger reaction, and as ligand in carbon–carbon bond formation reactions e.g. Suzuki, Heck, and Negishi coupling. The extensive use of PPh3 is inevitable to cause phosphorous pollution into the environment that would pose a potential danger to human health stimulating nerve, eyes, upper respiratory tract mucous membrane and skin. However, little attention had been paid for the detecting of PPh3. Traditionally, analysis of PPh3 in various matrices has been accomplished by spectrophotometric, titrimetric, chromatographic and high performance liquid chromatography(HPLC) methods. Unfortunately, those methods have limitations on the sensitivity and convenience. Therefore, in the chapter two of the thesis, we successfully design and synthesis the probe 1 based on Staudinger Legation, which is the product of commercial fluorescein reacting to 2-(2-azidophenyl)acetic acid. When the probe 1 react to PPh3, the fluorescence can be released.Fluorescent probes for biothiols including cysteine(Cys), homocysteine(Hcy), as well as reduced glutathione(GSH) have been the area of focus due to their significance in biological processes. Abnormal levels of Cys have been associated with many kinds of diseases such as slow growth, hair depigmentation, liver damage, loss of muscle and fat, skin lesion, and cancer. Hcy has been implicated in various types of vascular and renal diseases. Aberrant levels of GSH have been correlated with various diseases, such as cancer, AIDS, liver damage and neurodegenerative diseases. Thus, the detection of thiol is highly important for early diagnosis. In the chapter three of the thesis, based on the meso position of the dipyrrometheneboron difluoride(BODIPY), we use the acrylic ester and hydroquinone as the recognition groups to detect biothiols, formating the probe 3 and the probe 4.