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Synthesis of porphyrin-bis(polyazamacrocycle) triads via Suzuki coupling reaction

Institut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB, UMR 6302), 9 Avenue Alain Savary — BP 47870, 21078 Dijon Cedex, France

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Kiril P. Birin

Institut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB, UMR 6302), 9 Avenue Alain Savary — BP 47870, 21078 Dijon Cedex, France

Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky pr. 31, GSP-1, 119071 Moscow, Russia

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Sankar Muniappan

Institut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB, UMR 6302), 9 Avenue Alain Savary — BP 47870, 21078 Dijon Cedex, France

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Elena Ranyuk

Institut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB, UMR 6302), 9 Avenue Alain Savary — BP 47870, 21078 Dijon Cedex, France

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Yulia Yu. Enakieva

Institut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB, UMR 6302), 9 Avenue Alain Savary — BP 47870, 21078 Dijon Cedex, France

Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky pr. 31, GSP-1, 119071 Moscow, Russia

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Yulia G. Gorbunova

Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky pr. 31, GSP-1, 119071 Moscow, Russia

SPP full member in good standing.

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Christine Stern

Institut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB, UMR 6302), 9 Avenue Alain Savary — BP 47870, 21078 Dijon Cedex, France

SPP full member in good standing.

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Alla Bessmertnykh-Lemeune

Institut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB, UMR 6302), 9 Avenue Alain Savary — BP 47870, 21078 Dijon Cedex, France

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, and

Roger Guilard

Institut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB, UMR 6302), 9 Avenue Alain Savary — BP 47870, 21078 Dijon Cedex, France

Corresponding author, tel: +33 (0)380-396-111, fax: +33 (0)380-396-117.

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https://doi.org/10.1142/S1088424614500084Cited by:2

Abstract

Suzuki–Miyaura cross-coupling reaction has been used for the synthesis of tricyclic architectures based on trans-A₂B₂-porphyrins and bisaminal-protected polyazamacrocycles which are linked directly or by a p-phenylene spacer. This modular approach allowed the synthesis of ligands with various substituted porphyrin macrocycles and bisaminal-protected tetraazamacrocycles possessing different cavity sizes. These molecules can be assembled into dimers using a DABCO linker. Deprotection of these compounds afforded porphyrin-bis(polyazamacrocycle) triads.

Dedicated to Professor Aslan Tsivadze on the occasion of his 70th birthday

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Received 7 January 2014

Accepted 25 January 2014

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Synthesis of porphyrin-bis(polyazamacrocycle) triads via Suzuki coupling reaction

Abstract

References

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