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 journalArticle

17 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

Fingerprint

Porphyrins
Hydrogen bonds
Derivatives
Oxygen
Electrospray ionization
calix(4)arene
Mass spectrometry
Nuclear magnetic resonance

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Porphyrin capped with calix[4]arene derivative via hydrogen bonds. / Arai, Satoshi; Ohkawa, Haruki; Ishihara, Shinsuke; Shibue, Toshimichi; Takeoka, Shinji; Nishide, Hiroyuki.

In: Bulletin of the Chemical Society of Japan, Vol. 78, No. 11, 2005, p. 2007-2013.

Research output: Contribution to journalArticle

Arai, Satoshi ; Ohkawa, Haruki ; Ishihara, Shinsuke ; Shibue, Toshimichi ; Takeoka, Shinji ; Nishide, Hiroyuki. / Porphyrin capped with calix[4]arene derivative via hydrogen bonds. In: Bulletin of the Chemical Society of Japan. 2005 ; Vol. 78, No. 11. pp. 2007-2013.
@article{077b96e1c9b94063a56a616a8787bfb9,
title = "Porphyrin capped with calix[4]arene derivative via hydrogen bonds",
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.",
author = "Satoshi Arai and Haruki Ohkawa and Shinsuke Ishihara and Toshimichi Shibue and Shinji Takeoka and Hiroyuki Nishide",
year = "2005",
doi = "10.1246/bcsj.78.2007",
language = "English",
volume = "78",
pages = "2007--2013",
journal = "Bulletin of the Chemical Society of Japan",
issn = "0009-2673",
publisher = "Chemical Society of Japan",
number = "11",

}

TY - JOUR

T1 - Porphyrin capped with calix[4]arene derivative via hydrogen bonds

AU - Arai, Satoshi

AU - Ohkawa, Haruki

AU - Ishihara, Shinsuke

AU - Shibue, Toshimichi

AU - Takeoka, Shinji

AU - Nishide, Hiroyuki

PY - 2005

Y1 - 2005

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=33745730360&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33745730360&partnerID=8YFLogxK

U2 - 10.1246/bcsj.78.2007

DO - 10.1246/bcsj.78.2007

M3 - Article

AN - SCOPUS:33745730360

VL - 78

SP - 2007

EP - 2013

JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

SN - 0009-2673

IS - 11

ER -