β-Octabromo- and β-Octakis(trifluoromethyl)isocorroles: New Sterically Constrained Macrocyclic Ligands

Thomas, Kolle E.; Beavers, Christine M.; Gagnon, Kevin J.; Ghosh, Abhik

doi:10.1002/open.201700035

Title: β-Octabromo- and β-Octakis(trifluoromethyl)isocorroles: New Sterically Constrained Macrocyclic Ligands

Abstract

Here, we present a study of the acid-induced demetalation of two sterically hindered copper corroles, Cu β-octabromo-meso-triphenylcorrole (Cu[Br₈TPC]) and β-octakis(trifluoromethyl)-meso-tris(p-methoxyphenyl)corrole (Cu[(CF₃)₈TpOMePC]). Unlike reductive demetalation, which affords the free-base β-octabromocorrole, demetalation of Cu[Br₈TPC] under non- reductive conditions (CHCl₃/H₂SO₄) resulted in moderate yields of free-base 5- and 10-hydroxy isocorroles. The isomeric free bases could be complexed to Co^II and Ni^II, affording stable complexes. Only reductive demetalation was found to work for Cu[(CF₃)₈TpOMePC], affording a highly saddled, hydrated corrole, H₃[5-OH,10-H-(CF₃)₈TpOMePC], where the elements of water had added across C5 and C10. Interaction of this novel free base with Co^II resulted in Co[iso-10-H-[CF₃)₈TpOMePC], a Co^II 10-hydro isocorrole. Finally, the new metal complexes were all characterized by single-crystal X-ray diffraction analysis and, despite their sterically hindered nature, were found to exhibit almost perfectly planar isocorrole cores.

Authors:

Thomas, Kolle E. ^[1]; Beavers, Christine M. ^[2]; Gagnon, Kevin J. ^[2];

^[1]

Arctic Univ. of Norway, Tromso (Norway). Dept. of Chemistry, Center for Theoretical and Computational Chemistry
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Advanced Light Source

Publication Date:: Fri May 26 00:00:00 EDT 2017

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

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

OSTI Identifier:: 1413727

Grant/Contract Number:: AC02-05CH11231

Resource Type:: Accepted Manuscript

Journal Name:: ChemistryOpen

Additional Journal Information:: Journal Volume: 6; Journal Issue: 3; Journal ID: ISSN 2191-1363

Publisher:: ChemPubSoc Europe

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; corroles; isocorroles; macrocyclic ligands; near-infrared; single-crystal x-ray crystallography

Citation Formats


                    Thomas, Kolle E., Beavers, Christine M., Gagnon, Kevin J., and Ghosh, Abhik. β-Octabromo- and β-Octakis(trifluoromethyl)isocorroles: New Sterically Constrained Macrocyclic Ligands.  United States: N. p., 2017. 
Web.  doi:10.1002/open.201700035.

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                    Thomas, Kolle E., Beavers, Christine M., Gagnon, Kevin J., & Ghosh, Abhik. β-Octabromo- and β-Octakis(trifluoromethyl)isocorroles: New Sterically Constrained Macrocyclic Ligands.  United States.  https://doi.org/10.1002/open.201700035

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                    Thomas, Kolle E., Beavers, Christine M., Gagnon, Kevin J., and Ghosh, Abhik. Fri .  
"β-Octabromo- and β-Octakis(trifluoromethyl)isocorroles: New Sterically Constrained Macrocyclic Ligands".  United States.  https://doi.org/10.1002/open.201700035.  https://www.osti.gov/servlets/purl/1413727.

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@article{osti_1413727,

  title        = {β-Octabromo- and β-Octakis(trifluoromethyl)isocorroles: New Sterically Constrained Macrocyclic Ligands},

  author       = {Thomas, Kolle E. and Beavers, Christine M. and Gagnon, Kevin J. and Ghosh, Abhik},

  abstractNote = {Here, we present a study of the acid-induced demetalation of two sterically hindered copper corroles, Cu β-octabromo-meso-triphenylcorrole (Cu[Br8TPC]) and β-octakis(trifluoromethyl)-meso-tris(p-methoxyphenyl)corrole (Cu[(CF3)8TpOMePC]). Unlike reductive demetalation, which affords the free-base β-octabromocorrole, demetalation of Cu[Br8TPC] under non- reductive conditions (CHCl3/H2SO4) resulted in moderate yields of free-base 5- and 10-hydroxy isocorroles. The isomeric free bases could be complexed to CoII and NiII, affording stable complexes. Only reductive demetalation was found to work for Cu[(CF3)8TpOMePC], affording a highly saddled, hydrated corrole, H3[5-OH,10-H-(CF3)8TpOMePC], where the elements of water had added across C5 and C10. Interaction of this novel free base with CoII resulted in Co[iso-10-H-[CF3)8TpOMePC], a CoII 10-hydro isocorrole. Finally, the new metal complexes were all characterized by single-crystal X-ray diffraction analysis and, despite their sterically hindered nature, were found to exhibit almost perfectly planar isocorrole cores.},

  doi          = {10.1002/open.201700035},

  journal      = {ChemistryOpen},

  number       = 3,

  volume       = 6,

  place        = {United States},

  year         = {Fri May 26 00:00:00 EDT 2017},

  month        = {Fri May 26 00:00:00 EDT 2017}

}

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Works referenced in this record:

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Copper β-Octakis(trifluoromethyl)corroles: New Paradigms for Ligand Substituent Effects in Transition Metal Complexes
journal, November 2008

Thomas, Kolle Ekaney; Wasbotten, Ingar H.; Ghosh, Abhik
Inorganic Chemistry, Vol. 47, Issue 22
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A Metallocorrole with Orthogonal Pyrrole Rings
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Works referencing / citing this record:

Isocorroles as Homoaromatic NIR-Absorbing Chromophores: A First Quantum Chemical Study
journal, August 2018

Foroutan-Nejad, Cina; Larsen, Simon; Conradie, Jeanet
Scientific Reports, Vol. 8, Issue 1
DOI: 10.1038/s41598-018-29819-3

Rapid one-pot synthesis of pyrrole-appended isocorroles
journal, January 2019

Larsen, Simon; McCormick, Laura J.; Ghosh, Abhik
Organic & Biomolecular Chemistry, Vol. 17, Issue 12
DOI: 10.1039/c9ob00168a

Magnetic Diversity in Heteroisocorroles: Aromatic Pathways in 10-Heteroatom-Substituted Isocorroles
journal, November 2018

Foroutan-Nejad, Cina; Ghosh, Abhik
ACS Omega, Vol. 3, Issue 11
DOI: 10.1021/acsomega.8b02626

Isocorroles as Homoaromatic NIR-Absorbing Chromophores: A First Quantum Chemical Study
journal, August 2018

Foroutan-Nejad, Cina; Larsen, Simon; Conradie, Jeanet
Scientific Reports, Vol. 8, Issue 1
DOI: 10.1038/s41598-018-29819-3

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Other research related to this record:

CCDC 1532292: Experimental Crystal Structure Determination: VEXPIA : (2,3,7,8,12,13,17,18-octabromo-10-hydroxy-5,10,15-triphenylisocorrole)-(triphenylphosphine)-cobalt(iii) benzene solvate
dataset, June 2018

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Cambridge Structural Database (CSD)
DOI: 10.5517/ccdc.csd.cc1nfgsb
This dataset is a supplement to the current record

CCDC 1532288: Experimental Crystal Structure Determination
dataset, January 2021

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Cambridge Crystallographic Data Centre
DOI: 10.5517/ccdc.csd.cc1nfgn6
This dataset is a supplement to the current record

CCDC 1532291: Experimental Crystal Structure Determination
dataset, January 2021

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DOI: 10.5517/ccdc.csd.cc1nfgr9
This dataset is a supplement to the current record

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dataset (3)

Title: β-Octabromo- and β-Octakis(trifluoromethyl)isocorroles: New Sterically Constrained Macrocyclic Ligands

Abstract

Citation Formats

Synthesis and Characterization of Free-Base, Copper, and Nickel Isocorroles journal, June 2010

Demetalation of Silver(III) Corrolates journal, July 2009

Template Synthesis of Alkyl-Substituted Metal Isocorroles: Template Synthesis of Alkyl-Substituted Metal Isocorroles journal, June 2016

Investigation of Complementary Reactions of a Dipyrromethane with a Dipyrromethanemonocarbinol Leading to a 5-Isocorrole journal, February 2010

Reductive demetalation of copper corroles: first simple route to free-base β-octabromocorroles journal, August 2008

Structure and spectroscopic characterization of free base and metal complexes of 5,5-dimethyl-10,15-bis(pentafluorophenyl)isocorrole journal, January 2011

Synthesis of isocorrole and the higher homologues journal, March 2006

Electronic Absorption, Resonance Raman, and Electrochemical Studies of Planar and Saddled Copper(III) meso -Triarylcorroles. Highly Substituent-Sensitive Soret Bands as a Distinctive Feature of High-Valent Transition Metal Corroles journal, July 2002

Molecular structure of a gold β-octakis(trifluoromethyl)- meso -triarylcorrole: an 85° difference in saddling dihedral relative to copper journal, April 2012

Synthesis and structure of isocorrole metal complexes journal, February 2009

One-step synthesis of isocorroles journal, December 2007

Spiroconjugation in Spirodicorrolato-Dinickel(II) journal, November 2003

One-pot synthesis of meso -alkyl substituted isocorroles: the reaction of a triarylcorrole with Grignard reagent journal, August 2010

Synthesis and Functionalization of m eso -Aryl-Substituted Corroles journal, January 2001

Synthesis and chiroptical property of C2-symmetric cyclohexapyrrole journal, February 2007

Functionalization of the corrole ring: the role of isocorrole intermediates journal, January 2011

Demetalation of copper undecaarylcorroles: Molecular structures of a free-base undecaarylisocorrole and a gold undecaarylcorrole journal, September 2016

Copper β-Octakis(trifluoromethyl)corroles: New Paradigms for Ligand Substituent Effects in Transition Metal Complexes journal, November 2008

A Metallocorrole with Orthogonal Pyrrole Rings journal, March 2011

Template Synthesis of Alkyl-Substituted Metal Isocorroles journal, July 2016

Copper β-Octakis(trifluoromethyl)corroles: New Paradigms for Ligand Substituent Effects in Transition Metal Complexes journal, December 2008

Isocorroles as Homoaromatic NIR-Absorbing Chromophores: A First Quantum Chemical Study journal, August 2018

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Magnetic Diversity in Heteroisocorroles: Aromatic Pathways in 10-Heteroatom-Substituted Isocorroles journal, November 2018

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Synthesis and Characterization of Free-Base, Copper, and Nickel Isocorroles
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Demetalation of Silver(III) Corrolates
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Template Synthesis of Alkyl-Substituted Metal Isocorroles: Template Synthesis of Alkyl-Substituted Metal Isocorroles
journal, June 2016

Investigation of Complementary Reactions of a Dipyrromethane with a Dipyrromethanemonocarbinol Leading to a 5-Isocorrole
journal, February 2010

Reductive demetalation of copper corroles: first simple route to free-base β-octabromocorroles
journal, August 2008

Structure and spectroscopic characterization of free base and metal complexes of 5,5-dimethyl-10,15-bis(pentafluorophenyl)isocorrole
journal, January 2011

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journal, March 2006

Electronic Absorption, Resonance Raman, and Electrochemical Studies of Planar and Saddled Copper(III) meso -Triarylcorroles. Highly Substituent-Sensitive Soret Bands as a Distinctive Feature of High-Valent Transition Metal Corroles
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Molecular structure of a gold β-octakis(trifluoromethyl)- meso -triarylcorrole: an 85° difference in saddling dihedral relative to copper
journal, April 2012

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journal, February 2009

One-step synthesis of isocorroles
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Spiroconjugation in Spirodicorrolato-Dinickel(II)
journal, November 2003

One-pot synthesis of meso -alkyl substituted isocorroles: the reaction of a triarylcorrole with Grignard reagent
journal, August 2010

Synthesis and Functionalization of m eso -Aryl-Substituted Corroles
journal, January 2001

Synthesis and chiroptical property of C2-symmetric cyclohexapyrrole
journal, February 2007

Functionalization of the corrole ring: the role of isocorrole intermediates
journal, January 2011

Demetalation of copper undecaarylcorroles: Molecular structures of a free-base undecaarylisocorrole and a gold undecaarylcorrole
journal, September 2016

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A Metallocorrole with Orthogonal Pyrrole Rings
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Template Synthesis of Alkyl-Substituted Metal Isocorroles
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Rapid one-pot synthesis of pyrrole-appended isocorroles
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Magnetic Diversity in Heteroisocorroles: Aromatic Pathways in 10-Heteroatom-Substituted Isocorroles
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