Nickel(II) meso-Hydroxyporphyrin Complexes Revisited: Palladium-Catalysed Synthesis, Electronic Structures of Derived Oxy Radicals, and Oxidative Coupling to a Dioxoporphodimethene Dyad.
Identifieur interne : 002196 ( PubMed/Corpus ); précédent : 002195; suivant : 002197Nickel(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 ; Llew Rintoul ; Mean See Goh ; Khalissa Merahi ; Nathalie Parizel ; R Mark Wellard ; Sylvie Choua ; Dennis P. ArnoldSource :
- 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
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Nickel(II) meso-Hydroxyporphyrin Complexes Revisited: Palladium-Catalysed Synthesis, Electronic Structures of Derived Oxy Radicals, and Oxidative Coupling to a Dioxoporphodimethene Dyad.</title><author><name sortKey="Esdaile, Louisa J" sort="Esdaile, Louisa J" uniqKey="Esdaile L" first="Louisa J" last="Esdaile">Louisa J. Esdaile</name><affiliation><nlm:affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</nlm:affiliation></affiliation></author><author><name sortKey="Rintoul, Llew" sort="Rintoul, Llew" uniqKey="Rintoul L" first="Llew" last="Rintoul">Llew Rintoul</name><affiliation><nlm:affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</nlm:affiliation></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><nlm:affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</nlm:affiliation></affiliation></author><author><name sortKey="Merahi, Khalissa" sort="Merahi, Khalissa" uniqKey="Merahi K" first="Khalissa" last="Merahi">Khalissa Merahi</name><affiliation><nlm:affiliation>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex, France.</nlm:affiliation></affiliation></author><author><name sortKey="Parizel, Nathalie" sort="Parizel, Nathalie" uniqKey="Parizel N" first="Nathalie" last="Parizel">Nathalie Parizel</name><affiliation><nlm:affiliation>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex, France.</nlm:affiliation></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><nlm:affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</nlm:affiliation></affiliation></author><author><name sortKey="Choua, Sylvie" sort="Choua, Sylvie" uniqKey="Choua S" first="Sylvie" last="Choua">Sylvie Choua</name><affiliation><nlm:affiliation>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex, France.</nlm:affiliation></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><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></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2016">2016</date><idno type="RBID">pubmed:26833709</idno><idno type="pmid">26833709</idno><idno type="doi">10.1002/chem.201504252</idno><idno type="wicri:Area/PubMed/Corpus">002196</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002196</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Nickel(II) meso-Hydroxyporphyrin Complexes Revisited: Palladium-Catalysed Synthesis, Electronic Structures of Derived Oxy Radicals, and Oxidative Coupling to a Dioxoporphodimethene Dyad.</title><author><name sortKey="Esdaile, Louisa J" sort="Esdaile, Louisa J" uniqKey="Esdaile L" first="Louisa J" last="Esdaile">Louisa J. Esdaile</name><affiliation><nlm:affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</nlm:affiliation></affiliation></author><author><name sortKey="Rintoul, Llew" sort="Rintoul, Llew" uniqKey="Rintoul L" first="Llew" last="Rintoul">Llew Rintoul</name><affiliation><nlm:affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</nlm:affiliation></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><nlm:affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</nlm:affiliation></affiliation></author><author><name sortKey="Merahi, Khalissa" sort="Merahi, Khalissa" uniqKey="Merahi K" first="Khalissa" last="Merahi">Khalissa Merahi</name><affiliation><nlm:affiliation>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex, France.</nlm:affiliation></affiliation></author><author><name sortKey="Parizel, Nathalie" sort="Parizel, Nathalie" uniqKey="Parizel N" first="Nathalie" last="Parizel">Nathalie Parizel</name><affiliation><nlm:affiliation>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex, France.</nlm:affiliation></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><nlm:affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</nlm:affiliation></affiliation></author><author><name sortKey="Choua, Sylvie" sort="Choua, Sylvie" uniqKey="Choua S" first="Sylvie" last="Choua">Sylvie Choua</name><affiliation><nlm:affiliation>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex, France.</nlm:affiliation></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><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></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><pubmed><MedlineCitation Status="Publisher" Owner="NLM"><PMID Version="1">26833709</PMID><DateCreated><Year>2016</Year><Month>02</Month><Day>26</Day></DateCreated><DateRevised><Year>2016</Year><Month>02</Month><Day>26</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1521-3765</ISSN><JournalIssue CitedMedium="Internet"><Volume>22</Volume><Issue>10</Issue><PubDate><Year>2016</Year><Month>Mar</Month><Day>01</Day></PubDate></JournalIssue><Title>Chemistry (Weinheim an der Bergstrasse, Germany)</Title><ISOAbbreviation>Chemistry</ISOAbbreviation></Journal><ArticleTitle>Nickel(II) meso-Hydroxyporphyrin Complexes Revisited: Palladium-Catalysed Synthesis, Electronic Structures of Derived Oxy Radicals, and Oxidative Coupling to a Dioxoporphodimethene Dyad.</ArticleTitle><Pagination><MedlinePgn>3430-3446</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1002/chem.201504252</ELocationID><Abstract><AbstractText>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.</AbstractText><CopyrightInformation>© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Esdaile</LastName><ForeName>Louisa J</ForeName><Initials>LJ</Initials><AffiliationInfo><Affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Rintoul</LastName><ForeName>Llew</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Goh</LastName><ForeName>Mean See</ForeName><Initials>MS</Initials><AffiliationInfo><Affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Merahi</LastName><ForeName>Khalissa</ForeName><Initials>K</Initials><AffiliationInfo><Affiliation>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Parizel</LastName><ForeName>Nathalie</ForeName><Initials>N</Initials><AffiliationInfo><Affiliation>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Wellard</LastName><ForeName>R Mark</ForeName><Initials>RM</Initials><AffiliationInfo><Affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Choua</LastName><ForeName>Sylvie</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, BP 296 R8, 67008, Strasbourg Cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Arnold</LastName><ForeName>Dennis P</ForeName><Initials>DP</Initials><AffiliationInfo><Affiliation>School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia. d.arnold@qut.edu.au.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2016</Year><Month>02</Month><Day>02</Day></ArticleDate></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>Chemistry</MedlineTA><NlmUniqueID>9513783</NlmUniqueID><ISSNLinking>0947-6539</ISSNLinking></MedlineJournalInfo><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">EPR spectroscopy</Keyword><Keyword MajorTopicYN="N">NMR spectroscopy</Keyword><Keyword MajorTopicYN="N">density functional calculations</Keyword><Keyword MajorTopicYN="N">porphyrinoids</Keyword><Keyword MajorTopicYN="N">radicals</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2015</Year><Month>10</Month><Day>21</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2015</Year><Month>12</Month><Day>01</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2016</Year><Month>2</Month><Day>3</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2016</Year><Month>2</Month><Day>3</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2016</Year><Month>2</Month><Day>3</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">26833709</ArticleId><ArticleId IdType="doi">10.1002/chem.201504252</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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