Synthesis And Investigation Of Bf-based Fluorescent Dyes

Nowadays,great attention has been paid by chemists,physicist,and biologists due to broad application of small organic fluorescent molecules in material science and structural biology.Among the dye families,several organic fluorescent compounds with great potential application have been systemically engineered,such as coumarin,maphthalimide,cyanine,porphyrin,xanthene,and acid onium salt compounds.Due to their excellent photo-physical properties,these dyes were used as bio-imaging,photo-sensitizer,organic light-emitting diodes,nano-emitter,molecular machine,probes,solar energy collector,digital des ign,and information storage.BODIP Y,is one the fluorescent dyes that has been intensively investigated in the past decades.It is configured by two pyrrole rings with boron atom coordinated with the nitrogen atoms.Most BODIP Y derivatives have excellent photo-physical properties,such as higher molar extinguish coefficient,fluorescence quantum yield,larger Stokes' shift,good thermal/photo stability.The absorption and emission spectra could be modulated by the structure modification of BODIP Y.In this dissertation,a series of BODIPY and BOPHY derivatives were developed and their basic spectra were investigated in detail.In chapter 1,the fluorescent dyes were introduced,including the framework of BODIP Y and spectral properties.Application of BODIP Y der ivatives were also provided in the f ields of molecular machine,fluorescent probes,bio-imaging,and photodynamic therapy.In chanter 2,a series of BOPHY derivatives were developed by halogenation and coupling reaction.Therefore,the conjugate system was extended and moved their emission toward longer wavelength.Detailed investigation about their absorption and emission in var ious solution,polybicarbonate,and solid powder was provided.Higher fluorescent quamtum yields were found for these derivative in solution,film,and solid powder.In chapter 3,aldehyde was introduced to the framework of BODIPY by Vilsmeier-Hacck reactioin.Subsequently,it was coupled with various alkyne and them condensed with indanone,yielding a series of red fluorescent BODIPY derivatives.Detailed absorption and emission behavior in solution and film were presented.In chapter 4,condensation between BODIP Y-CHO derivatives and di-?2-picoly?amine were carried out and yielded a series of fluorescent probes towards Zn²⁺,Cd²⁺,Hg²⁺,Ba²⁺.Selectivity,sensitivity,and job plot were investigated in detail.In chapter 5,a photochromic triangle thiophene was condensed with di-?2-picoly?amine.Its response toward Zn²⁺ could be used to modulate the photoactivity of the triangle thiophene.Selectivity and thermal resistance were investigated.In chapter 6,conclusion and perspective were given.