Nucleophilic Thioglycosylation of Pentafluorophenyl-Substituted Porphyrinoids: Synthesis of Glycosylated Calix[n]phyrin and [28]Hexaphyrin Systems

The use of carbohydrate thiolates for facile, high-yielding, regio- and stereoselective nucleophilic substitution reactions of complex pentafluorophenyl-substituted porphyrinoids is reported. The title reaction has successfully been applied to calix[4]­phyrin, calix[6]­phyrin, and [28]­hexaphyrin su...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 14; pp. 5417 - 5420
Main Authors Klingenburg, René, Stark, Christian B. W, Wiehe, Arno
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.07.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
EXPANDED PORPHYRINS
DESIGN
GLYCOCONJUGATED PHOTOSENSITIZERS
CALIXPHYRINS
DERIVATIVES
MACROCYCLES
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Summary:The use of carbohydrate thiolates for facile, high-yielding, regio- and stereoselective nucleophilic substitution reactions of complex pentafluorophenyl-substituted porphyrinoids is reported. The title reaction has successfully been applied to calix[4]­phyrin, calix[6]­phyrin, and [28]­hexaphyrin substrates. The novel glycoporphyrinoid products with their extraordinary structures and unique photophysical properties are soluble in aqueous solutions and can serve as platforms for applications in biomedicine, catalysis, coordination, or redox chemistry.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01542