Synthesis and metal-binding properties of oligo-calixarenes. an approach towards the calix[4]arene-based dendrimers

Pavel Lhotak, Seiji Shinkai

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

A series of bis-calix[4]arene derivatives 4a-h (cone conformation) linked through the phenolic oxygens with the help of a single aliphatic chain (lower rim-lower rim connection) was obtained in high yields (50-80%) by alkylation of 25, 26, 27-tripropoxy-28-hydroxycalix[4]arenes 2a, 2b with 0.5 equiv. of Br-(CH2)n-Br in the presence of NaH. The same reaction with excess dibromides yielded corresponding bromoalkyl derivatives 3a-c which were used for construction of oligo-calix[4]arenes (bis, tris, pentakis) - a new family of calix[4]arene derivatives representing the first step on the way towards the calixarene-based dendrimers. The metal complexation behavior of newly prepared compounds was investigated with the help of 1H NMR spectroscopy.

Original languageEnglish
Pages (from-to)7681-7696
Number of pages16
JournalTetrahedron
Volume51
Issue number28
DOIs
Publication statusPublished - Jul 10 1995

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Calixarenes
Dendrimers
Metals
Derivatives
Alkylation
Magnetic Resonance Spectroscopy
Oxygen
Complexation
Nuclear magnetic resonance spectroscopy
Conformations
Cones
calix(4)arene

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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Synthesis and metal-binding properties of oligo-calixarenes. an approach towards the calix[4]arene-based dendrimers. / Lhotak, Pavel; Shinkai, Seiji.

In: Tetrahedron, Vol. 51, No. 28, 10.07.1995, p. 7681-7696.

Research output: Contribution to journalArticle

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