Porphyrin capped with calix[4]arene derivative via hydrogen bonds

Satoshi Arai, Haruki Ohkawa, Shinsuke Ishihara, Toshimichi Shibue, Shinji Takeoka, Hiroyuki Nishide

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

A calix[4]arene-porphyrin duplex was prepared by mixing equimolar amounts of hydroxy or carboxy calix[4]arene derivatives and pyridyl or o-aminophenylporphyrin derivatives. Electrospray ionization mass spectrometry (ESI-MS) was applied to screen a suitable pair of a calix[4]arene and a porphyrin. meso-Tetra(2-pyridyl)porphyrin formed a duplex with tetrahydroxy or tetrahydroxymethylcalix[4]arene via triple or quadruple hydrogen bonds. 1H NMR spectra showed that the tetrahydroxycalix[4]arene was symmetrically located upon the porphyrin ring, whereas trihydroxycalix[4]arene was slanted on the porphyrin ring. The duplex of meso-tetra(2-pyridyl) porphyrinatocobalt(II) and tetrahydroxymethylcalix[4]arene formed a complex with benzylimidazole, which was capable of reversible dioxygen-binding. The capping structure upon porphyrin provided by calix[4]arene raised the life-time of dioxygen-adduct compared with the porphyrin without calix[4]arene.

Original languageEnglish
Pages (from-to)2007-2013
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume78
Issue number11
DOIs
Publication statusPublished - 2005

ASJC Scopus subject areas

  • Chemistry(all)

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