Complexation of hydrogen bonding-driven preorganized di- and hexacationic bisporphyrin receptors for C60C(CO2-)2 in aqueous and DMSO media

doi:10.1016/j.tetlet.2007.08.029

Tetrahedron Letters

Volume 48, Issue 41, 8 October 2007, Pages 7327-7331

https://doi.org/10.1016/j.tetlet.2007.08.029 Get rights and content

Abstract

This Letter reports the synthesis of three dicationic and two hexacationic receptors in which two porphyrin units are connected with an aryl amide linker. ¹H NMR and X-ray crystal structure analysis for model compounds show that in aqueous or DMSO medium the receptors could adopt preorganized U-styled conformation due to intramolecular hydrogen bonding-induced rigidity of the amide linker. ¹H NMR, UV–vis and fluorescent investigations revealed that the ionic receptors efficiently complex C₆₀C $({CO}_{2}^{-})_{2}$ in aqueous medium with cooperative intermolecular electrostatic and donor–acceptor interactions as driving forces. A 1:1 binding stoichiometry has been established for the complexes and the related association constants have been evaluated.

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Acknowledgments

We thank the National Natural Science Foundation and the National Basic Research Program (2007CB808000) of China for financial support.

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Complexation of hydrogen bonding-driven preorganized di- and hexacationic bisporphyrin receptors for C60C(CO2-)2 in aqueous and DMSO media

Abstract

Graphical abstract

Section snippets

Acknowledgments

Eur. J. Org. Chem.

Eur. J. Biochem.

Chem. Asian J.

J. Am. Chem. Soc.

Angew. Chem., Int. Ed.

Org. Lett.

Acc. Chem. Res.

Curr. Opin. Chem. Biol.

Chem. Rev.

Curr. Opin. Chem. Biol.

Nature Chem. Biol.

Chem. Biodivers.

Top. Curr. Chem.

Acc. Chem. Res.

J. Org. Chem.

J. Am. Chem. Soc.

Angew. Chem., Int. Ed.

Chem. Commun.

J. Fluorine Chem.

Complexation of hydrogen bonding-driven preorganized di- and hexacationic bisporphyrin receptors for C₆₀ $C ({CO}_{2}^{-})_{2}$ in aqueous and DMSO media