Regioselective formylation of rhenium-oxo and gold corroles: substituent effects on optical spectra and redox potentials

Einrem, Rune F.; Jonsson, Einar Torfi; Teat, Simon J.; Settineri, Nicholas S.; Alemayehu, Abraham B.; Ghosh, Abhik

doi:10.1039/D1RA05525A

Title: Regioselective formylation of rhenium-oxo and gold corroles: substituent effects on optical spectra and redox potentials

Abstract

Vilsmeier–Haack formylation of ReO and Au meso-triarylcorroles over 16–18 hours affords moderate to good yields (47–65%) of the ReO-3-formyl and Au-3,17-diformyl derivatives in a highly regioselective manner. Formylation was found to effect substantial upshifts for redox potentials (especially the reduction potentials) as well as significant to dramatic redshifts for both the Soret and Q bands.

Authors:

Einrem, Rune F. ^[1]; Jonsson, Einar Torfi ^[1];

^[2];

^[3]; Alemayehu, Abraham B. ^[1];

^[1]

Department of Chemistry, UiT – The Arctic University of Norway, N-9037 Tromsø, Norway
Advanced Light Source, Lawrence Berkeley National Laboratory, Berkeley, CA 94720-8229, USA
Advanced Light Source, Lawrence Berkeley National Laboratory, Berkeley, CA 94720-8229, USA, Department of Chemistry, University of California, Berkeley, Berkeley, California 94720, USA

Publication Date:: 2021-10-18

Research Org.:: Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

Sponsoring Org.:: USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES). Materials Sciences & Engineering Division; Research Council of Norway; Arctic Center for Sustainable Energy at UiT

OSTI Identifier:: 1828088

Alternate Identifier(s):: OSTI ID: 1877587

Grant/Contract Number:: AC02-05CH11231; 262229; 324139

Resource Type:: Published Article

Journal Name:: RSC Advances

Additional Journal Information:: Journal Name: RSC Advances Journal Volume: 11 Journal Issue: 54; Journal ID: ISSN 2046-2069

Publisher:: Royal Society of Chemistry (RSC)

Country of Publication:: United Kingdom

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Einrem, Rune F., Jonsson, Einar Torfi, Teat, Simon J., Settineri, Nicholas S., Alemayehu, Abraham B., and Ghosh, Abhik. Regioselective formylation of rhenium-oxo and gold corroles: substituent effects on optical spectra and redox potentials.  United Kingdom: N. p., 2021. 
Web.  doi:10.1039/D1RA05525A.

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                    Einrem, Rune F., Jonsson, Einar Torfi, Teat, Simon J., Settineri, Nicholas S., Alemayehu, Abraham B., & Ghosh, Abhik. Regioselective formylation of rhenium-oxo and gold corroles: substituent effects on optical spectra and redox potentials.  United Kingdom.  https://doi.org/10.1039/D1RA05525A

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                    Einrem, Rune F., Jonsson, Einar Torfi, Teat, Simon J., Settineri, Nicholas S., Alemayehu, Abraham B., and Ghosh, Abhik. Mon .  
"Regioselective formylation of rhenium-oxo and gold corroles: substituent effects on optical spectra and redox potentials".  United Kingdom.  https://doi.org/10.1039/D1RA05525A.

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@article{osti_1828088,

  title        = {Regioselective formylation of rhenium-oxo and gold corroles: substituent effects on optical spectra and redox potentials},

  author       = {Einrem, Rune F. and Jonsson, Einar Torfi and Teat, Simon J. and Settineri, Nicholas S. and Alemayehu, Abraham B. and Ghosh, Abhik},

  abstractNote = {Vilsmeier–Haack formylation of ReO and Au meso-triarylcorroles over 16–18 hours affords moderate to good yields (47–65%) of the ReO-3-formyl and Au-3,17-diformyl derivatives in a highly regioselective manner. Formylation was found to effect substantial upshifts for redox potentials (especially the reduction potentials) as well as significant to dramatic redshifts for both the Soret and Q bands.},

  doi          = {10.1039/D1RA05525A},

  journal      = {RSC Advances},

  number       = 54,

  volume       = 11,

  place        = {United Kingdom},

  year         = {2021},

  month        = {10}

}

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Works referenced in this record:

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Title: Regioselective formylation of rhenium-oxo and gold corroles: substituent effects on optical spectra and redox potentials

Abstract

Citation Formats

Über die Einwirkung von Halogenphosphor auf Alkyl-formanilide. Eine neue Methode zur Darstellung sekundärer und tertiärer p -Alkylamino-benzaldehyde journal, January 1927

Heavy-element–ligand covalence: ligand noninnocence in molybdenum and tungsten Viking-helmet Corroles journal, January 2021

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Electrophilic Activation of Osmium-Nitrido Corroles: The OsN Triple Bond as a π-Acceptor Metallaligand in a Heterobimetallic Os VI N–Pt II Complex journal, March 2020

NIR-emissive iridium( iii ) corrole complexes as efficient singlet oxygen sensitizers journal, January 2015

Near-IR Phosphorescence of Iridium(III) Corroles at Ambient Temperature journal, July 2010

Selective Substitution of Corroles: Nitration, Hydroformylation, and Chlorosulfonation journal, May 2002

Rhenium Corrole Dimers: Electrochemical Insights into the Nature of the Metal–Metal Quadruple Bond journal, May 2021

Platinum corroles journal, January 2014

Stepwise Deoxygenation of Nitrite as a Route to Two Families of Ruthenium Corroles: Group 8 Periodic Trends and Relativistic Effects journal, April 2017

Gold Corroles as Near-IR Phosphors for Oxygen Sensing journal, September 2017

Amphiphilic aluminium(III) and gallium(III) corroles journal, March 2007

One-Pot Conversion of Fluorophores to Phosphorophores journal, November 2016

Gold corroles journal, February 2011

Synthesis and molecular structure of perhalogenated rhenium-oxo corroles journal, November 2020

Seven Clues to Ligand Noninnocence: The Metallocorrole Paradigm journal, March 2019

Fighting Cancer with Corroles journal, October 2016

Ambient-temperature near-IR phosphorescence and potential applications of rhenium-oxo corroles journal, January 2019

Oxidative Metalation as a Route to Size-Mismatched Macrocyclic Complexes: Osmium Corroles journal, October 2014

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Gold Tris(carboxyphenyl)corroles as Multifunctional Materials: Room Temperature Near-IR Phosphorescence and Applications to Photodynamic Therapy and Dye-Sensitized Solar Cells journal, July 2016

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Redox behavior of metallo oxtaethylporhyrins journal, August 1973

Relativistic effects in metallocorroles: comparison of molybdenum and tungsten biscorroles journal, January 2017

The Story of 5d Metallocorroles: From Metal–Ligand Misfits to New Building Blocks for Cancer Phototherapeutics journal, July 2021

Stable Platinum(IV) Corroles: Synthesis, Molecular Structure, and Room-Temperature Near-IR Phosphorescence journal, August 2018

Synthesis and Molecular Structure of Gold Triarylcorroles journal, December 2011

Vilsmeier Formylation of 5,10,15-Triphenylcorrole: Expected and Unusual Products journal, March 2003

SHELXT – Integrated space-group and crystal-structure determination journal, January 2015

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High-Valent Manganese Corroles and the First Perhalogenated Metallocorrole Catalyst journal, June 2001

Corrole photochemistry journal, September 2020

Synthesis and Molecular Structure of 99 Tc Corroles journal, November 2016

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Metal complexes of corrole
journal, June 2019

Electrophilic Activation of Osmium-Nitrido Corroles: The OsN Triple Bond as a π-Acceptor Metallaligand in a Heterobimetallic Os ^VI N–Pt ^II Complex
journal, March 2020

NIR-emissive iridium( iii ) corrole complexes as efficient singlet oxygen sensitizers
journal, January 2015

Near-IR Phosphorescence of Iridium(III) Corroles at Ambient Temperature
journal, July 2010

Selective Substitution of Corroles: Nitration, Hydroformylation, and Chlorosulfonation
journal, May 2002

Rhenium Corrole Dimers: Electrochemical Insights into the Nature of the Metal–Metal Quadruple Bond
journal, May 2021

Platinum corroles
journal, January 2014

Stepwise Deoxygenation of Nitrite as a Route to Two Families of Ruthenium Corroles: Group 8 Periodic Trends and Relativistic Effects
journal, April 2017

Gold Corroles as Near-IR Phosphors for Oxygen Sensing
journal, September 2017

Amphiphilic aluminium(III) and gallium(III) corroles
journal, March 2007

One-Pot Conversion of Fluorophores to Phosphorophores
journal, November 2016

Gold corroles
journal, February 2011

Synthesis and molecular structure of perhalogenated rhenium-oxo corroles
journal, November 2020

Seven Clues to Ligand Noninnocence: The Metallocorrole Paradigm
journal, March 2019

Fighting Cancer with Corroles
journal, October 2016

Ambient-temperature near-IR phosphorescence and potential applications of rhenium-oxo corroles
journal, January 2019

Oxidative Metalation as a Route to Size-Mismatched Macrocyclic Complexes: Osmium Corroles
journal, October 2014

Corroles as triplet photosensitizers
journal, January 2019

Gold Tris(carboxyphenyl)corroles as Multifunctional Materials: Room Temperature Near-IR Phosphorescence and Applications to Photodynamic Therapy and Dye-Sensitized Solar Cells
journal, July 2016

Metal-Ligand Misfits: Facile Access to Rhenium-Oxo Corroles by Oxidative Metalation
journal, December 2015

Redox behavior of metallo oxtaethylporhyrins
journal, August 1973

Relativistic effects in metallocorroles: comparison of molybdenum and tungsten biscorroles
journal, January 2017

The Story of 5d Metallocorroles: From Metal–Ligand Misfits to New Building Blocks for Cancer Phototherapeutics
journal, July 2021

Stable Platinum(IV) Corroles: Synthesis, Molecular Structure, and Room-Temperature Near-IR Phosphorescence
journal, August 2018

Synthesis and Molecular Structure of Gold Triarylcorroles
journal, December 2011

Vilsmeier Formylation of 5,10,15-Triphenylcorrole: Expected and Unusual Products
journal, March 2003

SHELXT – Integrated space-group and crystal-structure determination
journal, January 2015

Halterman Corroles and Their Use as a Probe of the Conformational Dynamics of the Inherently Chiral Copper Corrole Chromophore
journal, March 2018

Viking Helmet Corroles: Activating Inert Oxidometal Corroles
journal, September 2017

Synthesis and Molecular Structure of a Copper Octaiodocorrole
journal, May 2018

High-Valent Manganese Corroles and the First Perhalogenated Metallocorrole Catalyst
journal, June 2001

Corrole photochemistry
journal, September 2020

Synthesis and Molecular Structure of ⁹⁹ Tc Corroles
journal, November 2016

Rhenium-Imido Corroles
journal, April 2020

Metallocorroles as inherently chiral chromophores: resolution and electronic circular dichroism spectroscopy of a tungsten biscorrole
journal, January 2017

Strategies for Corrole Functionalization
journal, November 2016

Simple, Axial Ligand-Mediated Route to Water-Soluble Iridium Corroles
journal, June 2021

Gold(I) and Gold(III) Corroles
journal, October 2011

Functionalization of Corroles: Formylcorroles
journal, September 1997

Osmium-nitrido corroles as NIR indicators for oxygen sensors and triplet sensitizers for organic upconversion and singlet oxygen generation
journal, January 2016

Effect of Selective CF 3 Substitution on the Physical and Chemical Properties of Gold Corroles
journal, July 2017

Crystal structure refinement with SHELXL
journal, January 2015

Electrochemistry of Corroles in Nonaqueous Media
journal, November 2016

Tungsten Biscorroles: New Chiral Sandwich Compounds
journal, April 2016

Undecaphenylcorroles
journal, September 2012

Electronic Structure of Corrole Derivatives: Insights from Molecular Structures, Spectroscopy, Electrochemistry, and Quantum Chemical Calculations
journal, November 2016

A Metallocorrole with Orthogonal Pyrrole Rings
journal, March 2011