Selenium containing macrocycles:transformation between Se-N/Se-S/Se-Se bonds  

作　　者：Shaobo Ji Hicham El Mard Mario Smet Wim Dehaen Huaping Xu 

机构地区：[1]Key Laboratory of Organic Optoelectronics and Molecular Engineering,Department of Chemistry,Tsinghua University,Beijing 100084,China [2]Department of Chemistry,University of Leuven,Celestijnenlaan 20OF,B-3001 Heveriee(Leuven),Belgium

出　　处：《Science China Chemistry》2017年第9期1191-1196,共6页中国科学（化学英文版）

基　　金：supported by the National Science Foundation for Distinguished Young Scholars(21425416);the National Basic Research Program of China(2013CB834502);the Foundation for Innovative Research Groups of the National Natural Science Foundation of China(21421064);the National Natural Science Foundation of China(91427301)

摘　　要：Macrocycles possess potential applications in supramolecular chemistry and biosystems. Thus development of new kinds of macrocycles is of significance. Herein, novel macrocycles containing Se-Se/Se-S bonds were synthesized via transformation between selenium related dynamic covalent bonds. A monomer containing two ebselen moieties was synthesized (M1). The Se-N bonds in M1 were reduced by dithiothreitol, forming Se-S linked dimer (D1). To realize the transformation from Se-S bonds to Se-Se bonds, guest molecules were added as template, triggering the formation of Se-Se linked dimer (D2). The formation of these two new kinds of macrocycles was determined by H-1 NMR and Se-77 NMR, and the necessity of guest molecules was also confirmed. The introduction of ebselen moieties and Se-S bonds or Se-Se bonds into macrocycles may endow it with new responsiveness and bioactivities, as well as new types of host-guest chemistry.Macrocycles possess potential applications in supramolecular chemistry and biosystems.Thus development of new kinds of macrocycles is of significance.Herein,novel macrocycles containing Se-Se/Se-S bonds were synthesized via transformation between selenium related dynamic covalent bonds.A monomer containing two ebselen moieties was synthesized(M1).The Se-N bonds in M1 were reduced by dithiothreitol,forming Se-S linked dimer(D1).To realize the transformation from Se-S bonds to Se-Se bonds,guest molecules were added as template,triggering the formation of Se-Se linked dimer(D2).The formation of these two new kinds of macrocycles was determined by ~1H NMR and ^(77)Se NMR,and the necessity of guest molecules was also confirmed.The introduction of ebselen moieties and Se-S bonds or Se-Se bonds into macrocycles may endow it with new responsiveness and bioactivities,as well as new types of host-guest chemistry.

关 键 词：macrocycles  selenium  dynamic COVALENT BONDS 

分 类 号：O641.3[理学—物理化学]