Synthesis of a BINOL Derivative Fluorescent Sensor S-N,N'-(2,2'-dimethoxy-[1,1'-binaphthalene] -6,6'-diyl)bis (ethane-1,2-diamine)

Optically active fluorescent sensor containing a 1,1′-binaphthyl core and N,N’-diamine was synthesized and characterized by NMR spectroscopy. S-N1,N1'-(2,2'-dimethoxy-[1,1'-binaphthalene]-6,6'-diyl)bis (ethane-1,2-diamine) was synthesized by coupling reaction with Pd(dppf)Cl2 and Cu(phen)Cl2. Introduction 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 [1-6]. Optically active fluorescent sensors are also having increased attentions because they can provide real time analysis for the enantiomeric composition of chiral compounds and enhance the sensitivity in the detection of chiral substrates [7-15]. 1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol, popularly known as BINOL, has the phenomenon of atropisomerism, one stereoisomerism finding in systems where the rotation around a single bond which is restricted to yield different stereoisomers. Among the enantioselective fluorescent sensors synthesized, which based on chiral structure of 1,10-bi-2-naphthol (BINOL) have been highly investigated, and a few highly enantioselective fluores-cent sensors have been found for the recognition of R-hydroxycarboxylic acids, chiral amines, amino acids and amino alcohols. Because BINOL and its derivatives have the obvious different characteristic of special rigid structure, easy modification and the size of angle between two naphthalene ring freely adjusted, they are usually used to design and synthesis of that more efficient fluorescent probes which result in gaining increasing attention. Based on the versatile backbone of 1,1’-binaphthol, one new chiral fluorescent probe S-N1,N1'-(2,2'-dimethoxy-[1,1'-binaphthalene]-6,6'-diyl)bis (ethane-1,2-diamine) which may use to detect metal ion was synthesized in this article. It provides a new way of thinking and a certain foundation for the chiral binaphthol fluorescent probes study. Experimental Section Characterization: 1H NMR and 13C NMR spectra were collected on a Bruker AM-400WB spectrometer in chloroform-d as solvent and tetramethylsilane (TMS) as the internal standard. The mass spectra were obtained by using a Bruker Daltonics Autoflex II TOF system. Materials: CH3I (99.8%, anhydrous), dimethyl sulfoxide (DMSO), DCM and Br2 were purchased from Aldrich. Cu(phen)Cl2 , Pd(dppf)Cl2 , Na2S2O3, was purchased from J&KCHEMICAL Co. All reagents and chemicals were purchased from commercial sources (Aldrich, Acros, and Guoyao) and used without further purification unless stated otherwise. All solvents were distilled over appropriate drying agent(s) prior to use and were purged with nitrogen. 3rd Annual International Conference on Advanced Material Engineering (AME 2017) Copyright © 2017, the Authors. Published by Atlantis Press. This is an open access article under the CC BY-NC license (http://creativecommons.org/licenses/by-nc/4.0/). Advances in Engineering Research, volume 110