The Synthesis And Application Of Fluorescent Probes Based On Chiral BINOL Derivatives

Heavy metals and transition metals on the sustainable development of human society and the environment have a great influence.In the human body,a strong interaction between proteins and enzymes can be generated by heavy metals and transition metals,and make them lose activity,it also maybe enrich in some of the organs.If they exceed the limits of the content of human body tolerated which can do harm to human body,such as acute toxicity,subacute toxicity and chronic toxicity.The main pollution sources of heavy metals and transition metals are derived form industrial pollution,the second are the traffic pollution and living garbage pollution.Therefore,using of fluorescent probe real-time,fast and efficient detection the content of heavy metals and transition metals ions in environment samples and industrial waste water is urgent.Fluorescent probe is a kind of molecules which have character fluorescent from ultraviolet to near-infrared light area,and fluorescent property varies in some degree with the change of the environment.As the advantages of highly sensitivity,highly selectivity and convenient operation,fluorescent probe is widely used for detecting of cation,anion and neutral molecule.Because BINOL and its derivatives have the obvious characteristic of special rigid structure,easy modification and the size of angle between two naphthalene ring plane easily adjusted,they are often used to design and synthesis of more efficient fluorescent probes which result in gaining increasing attention.Based on the versatile backbone of 1,1'-binaphthol,four new chiral fluorescent probes which could detect silver ion and copper ion were synthesized in this article.We studied them optical property and application,therefore,some meaningful results were obtained.The details are as follow:1)the concept,design idea and recognition mechanism of fluorescent probes were briefly introduced.Some fluorescent probes for the detection and identification of ions and small molecules were summarized in recent years.2)Two new chiral fluorescent probes M1 and M2 based on binaphthol connected with glucose were synthesized.The study shows that only addition of Ag⁺to the solution of M1 could result in almost complete quenching of the intensity of fluorescent in methanol,however,other metal ions had no obvious fluorescence response behavior,and fluorescent intensity would decrease with the increase of concentration of silver ion.It was meant that it could be used as a specific fluorescent probe for Ag⁺over a wide range of competing cations.At the same time,upon the addition of Cu²⁺,the fluorescent intensity of M2 could result in almost complete quenching,so M2 could be used as a specific fluorescent probe for Cu²⁺over a wide range of competing cations.The fluorescent probes M1 and M2 have a good selectivity to Ag⁺and Cu²⁺,respectively,and the recognition process are barely interfered by other competing cations.3)Two new chiral fluorescent probes M3 and M4 based on binaphthol connected with coumarin were synthesized.The study shows that M3 have no selective recognition effect for any ions in acetontrile.However,only addition of Cu²⁺to the solution of M4 could result in almost complete quenching of the intensity of fluorescent in acetontrile,and other metal ions had on obvious fluorescent response behavior,so M4 could be used as specific fluorescent probe for Cu²⁺over a wide range of competing cations.The fluorescent probe M4 has a good selectivity to Cu²⁺,and the recognition process is also barely interfered by other competing cations.