An efficient synthesis of 4,4 ',5,5 '-tetraiododibenzo-24-crown-8 and its highly conjugated derivatives

作者：Pak JJ^*; Mayo JL; Shurdha E

来源：Tetrahedron Letters, 2006, 47(2): 233-237.

DOI：10.1016/j.tetlet.2005.10.147

• crown ether
• pseudorotaxane
• self-assembly
• alkyne
• conjugation

4,4',5,5'-Tetraiododibenzo-24-crown-8 (9), a practical building block, was prepared under efficient and mild reaction conditions starting from the simple starting material, catechol (1). Highly conjugated 4,4',5,5'-tetraethynyldibenzo-24-crown-8 (10a,b) were prepared via a Sonogashira, coupling reaction from tetraiodocrown ether 9. These highly conjugated crown ethers form complexes in CD2Cl2 with dibenzylammonium hexafluorophosphate in a 1:1 ratio. Emission spectrum of pseudorotaxane 11 shows a dramatic shift from the non-complexed precursor.

• 出版日期2006-1-9