Synthesis, Spectroscopic Properties And Application Of Novel BODIPY Fluorescent Dyes

BODIPY-based dyes as one of the versatile fluorophores have arousedtremendous attention because of their chemical stability, large molar absorptioncoefficients, high fluorescence quantum yields and narrow emission bands. In thepast few decades, these unique properties have attracted widespread interest ofapplications in fluorescent indicators, electroluminescent device, biotechnology andsolar concentrators. We have prepared thirteen BODIPY dyes with differentsubstituent group(B1-B13), two BODIPY dyes with thiol sulfu substituent group(L1-L2) as ligands, three coordination compound(C1-C3) use ligands of BODIPYand dipyridine. All newly synthesized BODIPY dyes are fully characterized by1H,13C,19F NMR spectroscopy and ESI mass spectrometry, the spectroscopic techniqueof the absorption and fluorescence are used to examin photophysical properties. Ourfocus on the application BODIPY dyes to photoelectric materials, fluorescentindicators and photocatalysis. Some significantly results are listed as follows:1. BODIPY dyes bearing oligo(ethylene glycol) groups on the meso-phenylping is expected to inhibit the intermolecular stacking and simultaneously todirect the molecular arrangement via C-H O and C-H F interactions in solid state.Indeed, we succeed in obtaining highly solid-state emissive BODIPY dyes byharnessing this simple strategy. In all cases, the meso-phenyl ring is nearlyperpendicular to the indacene plane. For B1, which has no substituents on themeso-phenyl ring, the molecules are arranged in a herringbone pattern in the abplane, the distance between neighboring indacene planes with partially overlappinghead-to-tail stacking being approximately3.8. For other ether chain decorateddyes B2B4, the alternate stacking of hydrophobic BODIPY cores and hydrophilicether chains results in the formation of a layered structure. Also, all the compoundsB1B5show strong photoluminescence with fluorescence quantum yields rangingfrom0.69to0.76and small Stokes shifts (~15nm) in dichloromethane. Uponexciting at365nm, B1in crystalline state merely exhibits weak fluorescence as aresult of ACQ, which is characteristic of Bodipy dyes in general. Gratifyingly,B2B4in crystalline state emit strongly in the red region with emission quantum yields of0.33,0.12, and0.06, respectively.2. The formation of dimers in the ground state is found to be responsible for thered emission in the condensed state and it displays concentration-dependentphotoluminescence in PMMA films. The PMMA films doped with B2-B4show twoseparated emission peaks; their relative intensity is concentration dependent, leadingto the fluorescence color varying from greenish yellow to red as the concentrationssuccessively increased from5to80wt%.3. Efficient OLEDs were fabricated by doping2wt%B2B4as emitters andgave high luminance, current efficiency, and external quantum efficiency of up to920cd m2,8.00cd A1, and2.15%, respectively, and these OLEDs also haveaggregation-induced photoluminescent change. Electrochemical and TGA studiessuggest that B1-B5are chemical and thermal stability, which is the basic of preparedstable OLEDs.4. BODIPY dyes bearing oligo(ethylene glycol) groups on the meso-phenylping, the lengthy hydrophilic ether will increase water soluble hydrophobic BODIPYcores, which attracted widespread interest of applications in drug carrier and cellimaging. As shown in the images of B5, these molecules can be easily taken up bythe cells. We did not observe any signs of morphological damage to the cells upontreatment with these chromophores for1to4h, which demonstrates their nontoxicity.5. The photocatalytic hydrogen production system make the realization ofhydrogen production ues undecorated BODIPY dyes (B1) as photosensitizer,whether electronic accepter or doner to the performance of BODIPY dyes (B6-B7)as photosensitizer is negative, and the effect of heavy atoms on the system of thehydrogen production rate of ascension is to shorten the system life of survival. Thenickel complexes(cat) as catalysts will decompose generate nanoparticles as the realcatalytic center, by modified BODIPY dyes (B8-B9) bring surface active uint tostable nanoparticles will improve the performance and live life of hydrogenproduction.Preliminary studies of complexes C1-C3show that the energy can bedelivered to the center of metal complexes from BODIPY, there is potentialapplications of organic dye and inorganic materials to efficient catalytic.