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

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

doi:10.1021/acs.inorgchem.7b01668

Title: Naphthylbipyrrole-Containing Amethyrin Analogue: A New Ligand for the Uranyl (UO₂²⁺) Cation

Abstract

Using naphthobipyrrole as a functional building block, a new expanded porphyrin, naphtho-isoamethyrin, was prepared in 85% yield under acid catalyzed [4+2] MacDonald coupling conditions. Here, treatment of naphtho-isoamethyrin with the non- aqueous uranyl silylamide salt, [UO₂[N(SiMe₃)₂]₂·2THF], yielded the corresponding uranyl complex. Upon metalation, naphtho-isoamethyrin undergoes a 2-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.

Authors:

^[1];

^[1]; Lee, Juhoon ^[1]; Vargas-Zúñiga, Gabriela I. ^[1];

^[1]; Lynch, Vincent M. ^[1];

^[1]

Univ. of Texas, Austin, TX (United States)

Publication Date:: Mon Aug 07 00:00:00 EDT 2017

Research Org.:: Univ. of Texas, Austin, TX (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES); R. A. Welch Foundation

OSTI Identifier:: 1735617

Grant/Contract Number:: FG02-01ER15186; F-0018

Resource Type:: Accepted Manuscript

Journal Name:: Inorganic Chemistry

Additional Journal Information:: Journal Volume: 56; Journal Issue: 16; Journal ID: ISSN 0020-1669

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Absorption; Ligands; Pyrroles; Cations; Macrocycles

Citation Formats


                    Anguera, Gonzalo, Brewster, II, James T., Moore, Matthew D., Lee, Juhoon, Vargas-Zúñiga, Gabriela I., Zafar, Hadiqa, Lynch, Vincent M., and Sessler, Jonathan L. Naphthylbipyrrole-Containing Amethyrin Analogue: A New Ligand for the Uranyl (UO22+) Cation.  United States: N. p., 2017. 
Web.  doi:10.1021/acs.inorgchem.7b01668.

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                    Anguera, Gonzalo, Brewster, II, James T., Moore, Matthew D., Lee, Juhoon, Vargas-Zúñiga, Gabriela I., Zafar, Hadiqa, Lynch, Vincent M., & Sessler, Jonathan L. Naphthylbipyrrole-Containing Amethyrin Analogue: A New Ligand for the Uranyl (UO22+) Cation.  United States.  https://doi.org/10.1021/acs.inorgchem.7b01668

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                    Anguera, Gonzalo, Brewster, II, James T., Moore, Matthew D., Lee, Juhoon, Vargas-Zúñiga, Gabriela I., Zafar, Hadiqa, Lynch, Vincent M., and Sessler, Jonathan L. Mon .  
"Naphthylbipyrrole-Containing Amethyrin Analogue: A New Ligand for the Uranyl (UO22+) Cation".  United States.  https://doi.org/10.1021/acs.inorgchem.7b01668.  https://www.osti.gov/servlets/purl/1735617.

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@article{osti_1735617,

  title        = {Naphthylbipyrrole-Containing Amethyrin Analogue: A New Ligand for the Uranyl (UO22+) Cation},

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

  abstractNote = {Using naphthobipyrrole as a functional building block, a new expanded porphyrin, naphtho-isoamethyrin, was prepared in 85% yield under acid catalyzed [4+2] MacDonald coupling conditions. Here, treatment of naphtho-isoamethyrin with the non- aqueous uranyl silylamide salt, [UO2[N(SiMe3)2]2·2THF], yielded the corresponding uranyl complex. Upon metalation, naphtho-isoamethyrin undergoes a 2-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.},

  doi          = {10.1021/acs.inorgchem.7b01668},

  journal      = {Inorganic Chemistry},

  number       = 16,

  volume       = 56,

  place        = {United States},

  year         = {Mon Aug 07 00:00:00 EDT 2017},

  month        = {Mon Aug 07 00:00:00 EDT 2017}

}

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Title: Naphthylbipyrrole-Containing Amethyrin Analogue: A New Ligand for the Uranyl (UO22+) Cation

Abstract

Citation Formats

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Title: Naphthylbipyrrole-Containing Amethyrin Analogue: A New Ligand for the Uranyl (UO₂²⁺) Cation

Molecular Design and Ordering Effects in π-Functional Materials for Transistor and Solar Cell Applications
journal, December 2011

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Synthetic and structural studies of sapphyrin, a 22-.pi.-electron pentapyrrolic "expanded porphyrin"
journal, March 1990

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journal, November 2003

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