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14. Expanding the Porphycene Core: Modification and Metalation.

Author

Brewster II, James T., Anguera, Gonzalo, and Sessler, Jonathan L.

Subjects
*METALATION, *CHEMICAL properties, *STRUCTURAL isomers, *CORE & periphery (Economic theory), *PORPHYRINS, *ISOMERS
Abstract

Porphycenes, the first structural isomer of porphyrin, display unique chemical and photophysical properties. In this Account , we detail our group's individual and collaborative efforts in elucidating further the chemical properties of porphycene. Particular emphasis will be placed on recent efforts devoted to expanding the porphycene core. 1 Introduction 2 Exploring the Chemistry of Porphycene 3 Synthesis and Metalation of an Expanded Porphycene 4 Conclusion [ABSTRACT FROM AUTHOR]

Published
2019
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19. Naphthylbipyrrole-Containing Amethyrin Analogue: A New Ligand for the Uranyl (UO22+) Cation

Author

Anguera, Gonzalo, Brewster, James T., Moore, Matthew D., Lee, Juhoon, Vargas-Zúñiga, Gabriela I., Zafar, Hadiqa, Lynch, Vincent M., and Sessler, Jonathan L.

Abstract

Using naphthobipyrrole as a functional building block, a new expanded porphyrin, naphthoisoamethyrin, was prepared in 85% yield under acid-catalyzed [4 + 2] MacDonald coupling conditions. Treatment of naphthoisoamethyrin with the nonaqueous uranyl silylamide salt [UO2[N(SiMe3)2]2·2THF] yielded the corresponding uranyl complex. Upon metalation, naphthoisoamethyrin undergoes a two-electron oxidation to yield a formal 22 π-electron aromatic species, as inferred from 1H NMR and UV–vis spectroscopy, as well as cyclic voltammetry.

Published
2024
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22. Porphycenes and Related Isomers: Synthetic Aspects.

Author

Anguera, Gonzalo and Sánchez-García, David

Subjects
*PORPHYCENES, *ISOMERS, *PORPHYRINS, *NAPHTHOL, *MATERIALS science
Abstract

Porphyrins, called the pigments of life, have been studied for decades. However, the first constitutional isomer of porphyrin, porphycene, was not synthesized until 1986. This milestone marked the beginning of a new era in the field of porphyrinoids and presented opportunities for the creation of an abundance of new pigments. The unique structural and electronic features of these compounds give rise to interesting physical and optical properties with applications in biomedicine and materials science. This review focuses on the synthetic methodologies available for the preparation of porphycenes (functionalized porphycenes, extended porphycenes, benzoporphycenes, naphthoporphycenes, and heteroanalogues) and the other known isomers, namely, corrphycene, hemiporphycene, and isoporphycene. Although the classical synthetic approaches are discussed, particular emphasis is placed on improvements to the known methodologies and recent advances in the field. [ABSTRACT FROM AUTHOR]

Published
2017
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24. Naphthylbipyrrole-Containing Amethyrin Analogue: A New Ligand for the Uranyl (UO 2 2+ ) Cation.

Author

Anguera G, Brewster JT 2nd, Moore MD, Lee J, Vargas-Zúñiga GI, Zafar H, Lynch VM, and Sessler JL

Abstract

Using naphthobipyrrole as a functional building block, a new expanded porphyrin, naphthoisoamethyrin, was prepared in 85% yield under acid-catalyzed [4 + 2] MacDonald coupling conditions. Treatment of naphthoisoamethyrin with the nonaqueous uranyl silylamide salt [UO 2 [N(SiMe 3 ) 2 ] 2 ·2THF] yielded the corresponding uranyl complex. Upon metalation, naphthoisoamethyrin undergoes a two-electron oxidation to yield a formal 22 π-electron aromatic species, as inferred from 1 H NMR and UV-vis spectroscopy, as well as cyclic voltammetry.

Published
2017
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