Regioselective Functionalization Of BODIPY Dyes Based On Cross Dehydrogenation Coupling Reaction

Boron-dipyrromethene?BODIPY?dyes have attracted wide research interests in recent years due to their excellent properties,very outstanding physical and chemical properties.They have found applications in a highly diverse research fields in biological detection,analytical chemistry,optical engineering,and material science.BODIPY can be modified by the modification of functional groups to change the corresponding optical properties,thereby increasing the application value of BODIPY.Therefore,the functional modification of BODIPY is of great significance to the practical application of BODIPY.This thesis mainly consists of two chapters.In Chapter 1,We have developed a cross-dehydrogenative coupling?CDC?reaction,which can be used to functionalize the ?-position of BODIPY dyes in a highly regioselective way.We started from a range of BODIPY dyes and coupled them with allylic alkenes or ethers using a catalyst system consisting of tetrabutylammonium iodide?Bu₄NI?and tertbutylhydroperoxide?tBuOOH,TBHP?.We obtained ?-functionalized alkenes which were previously difficult to access.A plausible mechanism was proposed for this reaction as the first functionation of BODIPY through radical process.The optical properties of the synthetic compounds were studied in the end.In Chapter 2,we have developed a one-pot reaction of the 3,5-position BODIPY acylation.A series of 3,5-formyl?acyl?-BODIPY derivatives were synthesized via useing 1,3-dioxolane compounds for functionalization of the alpha region,followed by hydrolysis by a one-pot process.The reaction provided a direct Synthesis of 3,5-formyl?acyl?-BODIPY Method.A series of?-acyl-BODIPY derivatives were synthesized by the corresponding acid chloride under the action of BF₃·Et₂O.The BODIPY of partially 3,5-formyl?acyl?was characterized by single crystal X-ray diffraction and the spectral properties of the synthesized compounds were studied.