The Synthesis And Application Of The Red And NIR BODIPY Fluorescent Sensors

4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes have been investigated intensively as labelling reagents, fluorescent switches, chemosensors and bioimaging owing to their favorable photophysical properties, such as high extinction coefficient, high fluorescence quantum yields (> 0.8), facile derivatization, and good photostability. In fluorescence bioimaging, fluorescence probes, which are used to recognize an anaylte, arouse more and more attention in the recent years. In order to get the useful bioimaging, the absorption and emission wavelength of fluorescence indicator in the range of "biological window" (650-1000 nm) become the interest of scientists. Herein, we successfully design and synthesize two series of fluorescence sensors in the near-infrared region and a series of one in the visible region, and also can be used to detect of an anaylte in the biological systems.We successfully achieve four chemosensors B7-B10 via through bond energy transfer in 2-(thiophen-2-yl)quinoline appended BODIPY cassettes. In particular, two energy transfer cassettes B7 and B10 consisting of 2-(thiophen-2-yl)quinoline (TQ) as a donor and BODIPY or NIR tetrastyryl-substituted BODIPY as an acceptor have been synthesized which produce ca.398 nm and 190 nm pseudo Stokes’shift for B10 and B7, respectively due to efficient through-bond energy transfer (up to 99%). Selectively binding between Fe (Ⅲ) and TQ significantly suppresses the excitation energy transfer and resulting in fluorescence quenching in aqueous solution and in living cells.With the different function moiety in the meso-position of BODIPY dyes, we have synthesized four novel compound B11-B14 of which 2-diphenylphosphinobenzstryl moiety is connected through a direct bond at 3,5-position. After oxidation of OH, the fluorescence intensity of compound B11-B14 has been increased. Other ROS and RNS failed to induce significant fluorescence amplification of compound B11-B14 in the NIR region with the emission band at 650 nm, making this system potentially valuable for studying the·OH in Hela cells upon stimulation of PMA.A novel selective fluorescent chemosensor B18 based on phenanthrene fused dipyrromethenes analogue binding with copper has been synthesized. It displays high selectivity and high sensitivity for H2S. The signal transduction occurs via separation of complex B18 to free compound of phenanthrene fused dipyrromethenes B17 and CuS. Utilization of metal-anion affinity that sulfide is known to react with copper ions to form a very stable CuS species for a low-solubility product constant has been reported as an important reason. Its potential for biological application is confirmed by employing it for fluorescence imaging of H2S in live cells.