Nickel(II) meso-Hydroxyporphyrin Complexes Revisited: Palladium-Catalysed Synthesis, Electronic Structures of Derived Oxy Radicals, and Oxidative Coupling to a Dioxoporphodimethene Dyad.
Identifieur interne : 001A45 ( Main/Exploration ); précédent : 001A44; suivant : 001A46Nickel(II) meso-Hydroxyporphyrin Complexes Revisited: Palladium-Catalysed Synthesis, Electronic Structures of Derived Oxy Radicals, and Oxidative Coupling to a Dioxoporphodimethene Dyad.
Auteurs : Louisa J. Esdaile [Australie] ; Llew Rintoul [Australie] ; Mean See Goh [Australie] ; Khalissa Merahi [France] ; Nathalie Parizel [France] ; R Mark Wellard [Australie] ; Sylvie Choua [France] ; Dennis P. Arnold [Australie]Source :
- Chemistry (Weinheim an der Bergstrasse, Germany) [ 1521-3765 ] ; 2016.
Abstract
We report the synthesis and characterisation of new examples of meso-hydroxynickel(II) porphyrins with 5,15-diphenyl and 10-phenyl-5,15-diphenyl/diaryl substitution. The OH group was introduced by using carbonate or hydroxide as nucleophile by using palladium/phosphine catalysis. The NiPor-OHs exist in solution in equilibrium with the corresponding oxy radicals NiPor-O(.) . The 15-phenyl group stabilises the radicals, so that the (1) H NMR spectra of {NiPor-OH} are extremely broad due to chemical exchange with the paramagnetic species. The radical concentration for the diphenylporphyrin analogue is only 1 %, and its NMR line-broadening was able to be studied by variable-temperature NMR spectroscopy. The EPR signals of NiPor-O(.) are consistent with somewhat delocalised porphyrinyloxy radicals, and the spin distributions calculated by using density functional theory match the EPR and NMR spectroscopic observations. Nickel(II) meso-hydroxy-10,20-diphenylporphyrin was oxidatively coupled to a dioxo-terminated porphodimethene dyad, the strongly red-shifted electronic spectrum of which was successfully modelled by using time-dependent DFT calculations.
DOI: 10.1002/chem.201504252
PubMed: 26833709
Affiliations:
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Esdaile</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001</wicri:regionArea><wicri:noRegion>4001</wicri:noRegion></affiliation></author><author><name sortKey="Rintoul, Llew" sort="Rintoul, Llew" uniqKey="Rintoul L" first="Llew" last="Rintoul">Llew Rintoul</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001</wicri:regionArea><wicri:noRegion>4001</wicri:noRegion></affiliation></author><author><name sortKey="Goh, Mean See" sort="Goh, Mean See" uniqKey="Goh M" first="Mean See" last="Goh">Mean See Goh</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001</wicri:regionArea><wicri:noRegion>4001</wicri:noRegion></affiliation></author><author><name sortKey="Merahi, Khalissa" sort="Merahi, Khalissa" uniqKey="Merahi K" first="Khalissa" last="Merahi">Khalissa Merahi</name><affiliation wicri:level="4"><nlm:affiliation>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex</wicri:regionArea><wicri:noRegion>67008, Strasbourg Cedex</wicri:noRegion><orgName type="university">Université de Strasbourg</orgName><placeName><settlement type="city">Strasbourg</settlement><region type="region" nuts="2">Grand Est</region><region type="old region" nuts="2">Alsace (région administrative)</region></placeName></affiliation></author><author><name sortKey="Parizel, Nathalie" sort="Parizel, Nathalie" uniqKey="Parizel N" first="Nathalie" last="Parizel">Nathalie Parizel</name><affiliation wicri:level="4"><nlm:affiliation>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex</wicri:regionArea><wicri:noRegion>67008, Strasbourg Cedex</wicri:noRegion><orgName type="university">Université de Strasbourg</orgName><placeName><settlement type="city">Strasbourg</settlement><region type="region" nuts="2">Grand Est</region><region type="old region" nuts="2">Alsace (région administrative)</region></placeName></affiliation></author><author><name sortKey="Wellard, R Mark" sort="Wellard, R Mark" uniqKey="Wellard R" first="R Mark" last="Wellard">R Mark Wellard</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001</wicri:regionArea><wicri:noRegion>4001</wicri:noRegion></affiliation></author><author><name sortKey="Choua, Sylvie" sort="Choua, Sylvie" uniqKey="Choua S" first="Sylvie" last="Choua">Sylvie Choua</name><affiliation wicri:level="4"><nlm:affiliation>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex</wicri:regionArea><wicri:noRegion>67008, Strasbourg Cedex</wicri:noRegion><orgName type="university">Université de Strasbourg</orgName><placeName><settlement type="city">Strasbourg</settlement><region type="region" nuts="2">Grand Est</region><region type="old region" nuts="2">Alsace (région administrative)</region></placeName></affiliation></author><author><name sortKey="Arnold, Dennis P" sort="Arnold, Dennis P" uniqKey="Arnold D" first="Dennis P" last="Arnold">Dennis P. Arnold</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia. d.arnold@qut.edu.au.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001</wicri:regionArea><wicri:noRegion>4001</wicri:noRegion></affiliation></author></analytic><series><title level="j">Chemistry (Weinheim an der Bergstrasse, Germany)</title><idno type="eISSN">1521-3765</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">We report the synthesis and characterisation of new examples of meso-hydroxynickel(II) porphyrins with 5,15-diphenyl and 10-phenyl-5,15-diphenyl/diaryl substitution. The OH group was introduced by using carbonate or hydroxide as nucleophile by using palladium/phosphine catalysis. The NiPor-OHs exist in solution in equilibrium with the corresponding oxy radicals NiPor-O(.) . The 15-phenyl group stabilises the radicals, so that the (1) H NMR spectra of {NiPor-OH} are extremely broad due to chemical exchange with the paramagnetic species. The radical concentration for the diphenylporphyrin analogue is only 1 %, and its NMR line-broadening was able to be studied by variable-temperature NMR spectroscopy. The EPR signals of NiPor-O(.) are consistent with somewhat delocalised porphyrinyloxy radicals, and the spin distributions calculated by using density functional theory match the EPR and NMR spectroscopic observations. Nickel(II) meso-hydroxy-10,20-diphenylporphyrin was oxidatively coupled to a dioxo-terminated porphodimethene dyad, the strongly red-shifted electronic spectrum of which was successfully modelled by using time-dependent DFT calculations.</div></front></TEI><affiliations><list><country><li>Australie</li><li>France</li></country><region><li>Alsace (région administrative)</li><li>Grand Est</li></region><settlement><li>Strasbourg</li></settlement><orgName><li>Université de Strasbourg</li></orgName></list><tree><country name="Australie"><noRegion><name sortKey="Esdaile, Louisa J" sort="Esdaile, Louisa J" uniqKey="Esdaile L" first="Louisa J" last="Esdaile">Louisa J. Esdaile</name></noRegion><name sortKey="Arnold, Dennis P" sort="Arnold, Dennis P" uniqKey="Arnold D" first="Dennis P" last="Arnold">Dennis P. Arnold</name><name sortKey="Goh, Mean See" sort="Goh, Mean See" uniqKey="Goh M" first="Mean See" last="Goh">Mean See Goh</name><name sortKey="Rintoul, Llew" sort="Rintoul, Llew" uniqKey="Rintoul L" first="Llew" last="Rintoul">Llew Rintoul</name><name sortKey="Wellard, R Mark" sort="Wellard, R Mark" uniqKey="Wellard R" first="R Mark" last="Wellard">R Mark Wellard</name></country><country name="France"><region name="Grand Est"><name sortKey="Merahi, Khalissa" sort="Merahi, Khalissa" uniqKey="Merahi K" first="Khalissa" last="Merahi">Khalissa Merahi</name></region><name sortKey="Choua, Sylvie" sort="Choua, Sylvie" uniqKey="Choua S" first="Sylvie" last="Choua">Sylvie Choua</name><name sortKey="Parizel, Nathalie" sort="Parizel, Nathalie" uniqKey="Parizel N" first="Nathalie" last="Parizel">Nathalie Parizel</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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