Synthesis And Properties Of [4] Helicene

Spiral phenomenon exists in nature throughout every corner of the modern life.In recent years,spiral compounds have become one of the hotspots of organic chemistry because of its structure.Functionalized spiral compounds not only have excellent optical and electrical properties,but also can be widely used in liquid crystal materials,nonlinear optical materials and chiral optical materials.Moreover,since the spiral compound has a stable conjugated skeleton,and Which can be used in chiral synthesis,asymmetric catalysis,chiral molecular recognition and molecular machinery.1,1'-bi-2-naphthol is a hexagonal aromatic compound with a C2 axis,which is a hot spot for scientists because of its special stereochemical properties.Binaphthol-based derivatization also show a broad application prospects because of its unique nature in many areas.At present,most researches on the synthesis and application of spiral compounds are only limited to achiral spiralenes and their analogues,but little is known about the synthesis and application of chiral spiralenes and their analogues.Because the existing synthesis methods of chiral spiralenes and their analogues are rare,their synthesis step is too long,the reaction conditions are harsh(mostly low temperature,absolute anhydrous anaerobic reaction),their yield is low,the enantioselective is poor,side effects is more and other deficiencies.Therefore,the chiral spiral ligand or catalyst which can be used in the asymmetric synthesis is still too little,and the asymmetric reaction catalyzed by chiral spiral is still limited.Therefore,we use(R)(S)chiral BINOL as the matrix,through a number of simple reactions and easy raw materials,selecting the highly selective reaction in BINOL before and after the two sides,trying to chiral power induce spiral phenomenon,finally could get series with the basic chiral [4]helicene and complex multi-helicene,and characterizetheir structure by using nuclear magneticspectroscopy,elemental analysis,and using of UV absorption spectroscopy,fluorescence spectroscopy in the photoelectric characteristics,in order to put them in molecular recognition and chiral catalysis.At the same time,on the basis of the binaphthyl dicarboxylate,the Wittig reaction with the phosphorus leiside reagent with the structure of stilbene was mild and the yield was high,and the binaphthol derivative with large conjugated structure was obtained.It is very important to synthesize the novel binaphthol derivatives.