Document Detail


Clickable Di- and Tetra-Functionalized Pillar[n]arenes (n = 5, 6) by Oxidation-Reduction of Pillar[n]arene Units.
MedLine Citation:
PMID:  23198965     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
We report a new route for the selective synthesis of di- and tetra-functionalized pillararenes via oxidation and reduction of the pillararene units. Hypervalent-iodine oxidation of perethylated pillar[5]arene afforded pillar[5]arene derivatives containing one benzoquinone unit and two benzoquinones at the A,B- and A,C-units. A pillar[6]arene derivative containing one benzoquinone unit was also synthesized. Reduction of the benzoquinone units yielded position-selective di- and tetra-hydroxylated pillararene derivatives. This methodology avoids the generation of many constitutional isomers and overcomes the isolation problem of numerous constitutional isomers. From these hydroxylated pillararenes, Huisgen reaction-based clickable di- and tetra-alkynylated pillar[5]arenes were prepared. Because of the highly selective and reactive nature of Huisgen alkyne-azide cycloaddition, these pillar[5]arenes can serve as key compounds for a large library of di- and tetra-functionalized pillararenes. Based on these di- and tetra-functionalized pillar[5]arenes as key compounds, fluorescent sensors were created by the modification of di- and tetra-pyrene moieties via Huisgen type click reactions.
Authors:
Tomoki Ogoshi; Daiki Yamafuji; Daisuke Kotera; Takamichi Aoki; Shuhei Fujinami; Tada-Aki Yamagishi
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-12-3
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 Dec 
Date Detail:
Created Date:  2012-12-3     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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