Synthesis Of Methylthio Aryl Atriynes For Application In The Self-assembly Of Gold Nanoparticles

Many researchers have great interest in the field of nanotechnology with0.1~100nm nanoparticles in recent decades. With the in-depth studies, people have foundthat different scales of nanoparticle or nanoclusters have completely different materialproperties and movement rules. In many literatures, it is suggested that methylthioarylethynes with different sizes, geometric shapes and numbers of–SCH3groups,have great influence in the field of gold nanoparticle cluster assembly.5-arylpenta-2,4-diyn-1-ols can be used in the field of organic synthesis asimportant synthetic intermediate due to the unsaturated acetylene bond, high chemicalactive hydroxyl and conjugated structure with rich electrons. Many functionalconjugate arayl diynes compounds and heterocyclic compounds can be obtainedthrough modification of terminal hydroxyl. Many bioactive drug intermediates canbe synthesized though intramolecular or intermolecular cyclization which haveextensive applications in the field of medicine. Moreover,5-arylpenta-2,4-diyn-1-olswith high optical activity have important research value and promising future in thefield of optoelectronic materials.The purpose of this study was to present an universal and efficient method for thesynthesis of different5-arylpenta-2,4-diyn-1-ols. On the basis of our laboratorialworks, we expanded terminal functional buliding blocks from methylthio arylethynes,methylthio aryl diynes to the methylthio aryl atriynes. It will have importantapplication in the field of on gold nanoparticle self-assembly. This main contents ofthis article as follows:Firstly, the application of acetylene alcohols in organic synthesis, generalsynthetic method of acetylene alcohols and methylthio arylethynes, the field of goldnanoparticle self-assembly were introduced. On the basis of previous works of ourlaboratory, we came up with the purpose of this study.Secondly, we came up with the method based on Cadiot-Chodkiewicz coupling tosynthesize5-arylpenta-2,4-diyn-1-ol after comparing the two kinds of diffierentsynthetic methods. Different substituted aromatic acetylene bromide were synthesizedthrough diazotization, Sonogashira coupling, NBS bromination methods. TraditionalCadiot-Chodkiewicz coupling conditions were changed to improve the yield ofdifferent substituted5-arylpenta-2,4-diyn-1-ols. Thirdly, the modified Ogura method was used to prepare MP-S. Methylthio arylatriynes with active links groups was synthesized from5-(4-iodophenyl)penta-2,4-diyn-1-ol through oxidation reaction, one-pot reaction. This method has theadvantages of simple operation, available raw materials, high yield in the synthesis ofmethylthio arylethynes...