Design and synthesis of a C4-symmetrical hard-soft ditopic metal receptor by calixarene-porphyrin coupling

Takeshi Nagasaki, Hiroyuki Fujishima, Masayuki Takeuchi, Seiji Shinkai

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

A tetraphenylporphyrin capped with a calix[4]aryl amide through L-alanine pillars (compound 1) has been synthesized. Owing to C4 symmetry in both the tetraphenylporphyrin and the calix[4]arene this molecule still retains C4 symmetry. As the calix[4]aryl amide moiety can bind alkali metal cations, and the porphyrin moiety can bind transition metal cations, compound 1 acts as a host molecule with a hard-soft ditopic metal-binding site. It was found that the ZnII complex of 1 (complex 1-ZnII) can bind KI very strongly with log Kass = 5.23 (CHCI3:MeCN = 4:1 v/v; 25 °C) whereas KC104 is scarcely captured by 1-ZnII. Absorption and fluorescence spectroscopic studies showed that I- ion is bound to this cavity, interacting with both calix[4]arene-bound K+ through electrostatic attraction and porphyrin-bound ZnII through coordination as an axial ligand. The results establish that complex 1-ZnII acts as a unique ditopic receptor for I- ion.

Original languageEnglish
Pages (from-to)1883-1888
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
Publication statusPublished - Jan 1 1995

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Calixarenes
Porphyrins
Amides
Cations
Metals
Ions
Alkali Metals
Molecules
Alanine
Transition metals
Electrostatics
Fluorescence
Binding Sites
Ligands
calix(4)arene
tetraphenylporphyrin

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Design and synthesis of a C4-symmetrical hard-soft ditopic metal receptor by calixarene-porphyrin coupling. / Nagasaki, Takeshi; Fujishima, Hiroyuki; Takeuchi, Masayuki; Shinkai, Seiji.

In: Journal of the Chemical Society, Perkin Transactions 1, 01.01.1995, p. 1883-1888.

Research output: Contribution to journalArticle

Nagasaki, Takeshi ; Fujishima, Hiroyuki ; Takeuchi, Masayuki ; Shinkai, Seiji. / Design and synthesis of a C4-symmetrical hard-soft ditopic metal receptor by calixarene-porphyrin coupling. In: Journal of the Chemical Society, Perkin Transactions 1. 1995 ; pp. 1883-1888.
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