Coreceptor molecules. Synthesis of metalloreceptors containing porphyrin subunits and formation of mixed substrate supermolecules by binding of organic substrates and of metal ions

Andrew Hamilton, Jean Marie Lehn, Jonathan L. Sessler

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Abstract

Three coreceptor molecules, two macrotetracycles 1 and 2 and one macropentacycle 3, containing [18]-N2O4 macrocyclic and porphyrinic subunits, have been synthesized and characterized. They form metalloreceptors by complexation of transition-metal ions like Zn(II) or Cu(II) with the porphyrin groups. Binding of α,ω-diammonium cations to the [18]-N2O4 units occurs with substrate inclusion, yielding η2-cryptates like 27, 28, and 31, as indicated by very large upfield shifts of the CH2 proton NMR signals of the substrates. Similarly, these organic cations also bind to the Zn(II)-containing metalloreceptors 19, 20 and 22, giving organic/inorganic mixed substrate supermolecules, such as 29, 30, and 32. In these and similar species, the simultaneous complexation of several substrates opens the way to the study of mutual interactions within supramolecular structures and of regulation effects on physical and chemical properties.

Original languageEnglish (US)
Pages (from-to)5158-5167
Number of pages10
JournalJournal of the American Chemical Society
Volume108
Issue number17
StatePublished - 1986

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Porphyrins
Metal ions
Cations
Metals
Ions
Crown Ethers
Molecules
Substrates
Complexation
Protons
Positive ions
Chemical properties
Transition metals
Physical properties
Nuclear magnetic resonance

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "Three coreceptor molecules, two macrotetracycles 1 and 2 and one macropentacycle 3, containing [18]-N2O4 macrocyclic and porphyrinic subunits, have been synthesized and characterized. They form metalloreceptors by complexation of transition-metal ions like Zn(II) or Cu(II) with the porphyrin groups. Binding of α,ω-diammonium cations to the [18]-N2O4 units occurs with substrate inclusion, yielding η2-cryptates like 27, 28, and 31, as indicated by very large upfield shifts of the CH2 proton NMR signals of the substrates. Similarly, these organic cations also bind to the Zn(II)-containing metalloreceptors 19, 20 and 22, giving organic/inorganic mixed substrate supermolecules, such as 29, 30, and 32. In these and similar species, the simultaneous complexation of several substrates opens the way to the study of mutual interactions within supramolecular structures and of regulation effects on physical and chemical properties.",
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AU - Hamilton, Andrew

AU - Lehn, Jean Marie

AU - Sessler, Jonathan L.

PY - 1986

Y1 - 1986

N2 - Three coreceptor molecules, two macrotetracycles 1 and 2 and one macropentacycle 3, containing [18]-N2O4 macrocyclic and porphyrinic subunits, have been synthesized and characterized. They form metalloreceptors by complexation of transition-metal ions like Zn(II) or Cu(II) with the porphyrin groups. Binding of α,ω-diammonium cations to the [18]-N2O4 units occurs with substrate inclusion, yielding η2-cryptates like 27, 28, and 31, as indicated by very large upfield shifts of the CH2 proton NMR signals of the substrates. Similarly, these organic cations also bind to the Zn(II)-containing metalloreceptors 19, 20 and 22, giving organic/inorganic mixed substrate supermolecules, such as 29, 30, and 32. In these and similar species, the simultaneous complexation of several substrates opens the way to the study of mutual interactions within supramolecular structures and of regulation effects on physical and chemical properties.

AB - Three coreceptor molecules, two macrotetracycles 1 and 2 and one macropentacycle 3, containing [18]-N2O4 macrocyclic and porphyrinic subunits, have been synthesized and characterized. They form metalloreceptors by complexation of transition-metal ions like Zn(II) or Cu(II) with the porphyrin groups. Binding of α,ω-diammonium cations to the [18]-N2O4 units occurs with substrate inclusion, yielding η2-cryptates like 27, 28, and 31, as indicated by very large upfield shifts of the CH2 proton NMR signals of the substrates. Similarly, these organic cations also bind to the Zn(II)-containing metalloreceptors 19, 20 and 22, giving organic/inorganic mixed substrate supermolecules, such as 29, 30, and 32. In these and similar species, the simultaneous complexation of several substrates opens the way to the study of mutual interactions within supramolecular structures and of regulation effects on physical and chemical properties.

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