Synthesis and optical limiting properties of axially bridged phthalocyanines: [(tBu4PcGa)2O] and [(tBu4PcIn)2O].
Identifieur interne : 003442 ( Main/Exploration ); précédent : 003441; suivant : 003443Synthesis and optical limiting properties of axially bridged phthalocyanines: [(tBu4PcGa)2O] and [(tBu4PcIn)2O].
Auteurs : RBID : pubmed:12298016Abstract
Highly soluble [(tBu(4)PcM)(2)O] phthalocyanine dimers (M=Ga(III) (3), In(III) (4)) were prepared by the reaction of [tBu(4)PcMCl] (M=Ga(III) (1), In(III) (2)) with excess of concentrated H(2)SO(4) at -20 degrees C. The Mbond;Obond;M linkages in 3 and 4 are not stable against concentrated H(2)SO(4) at room temperature, 6 n HCl at reflux, or during isolation under column chromatographic conditions (e.g. silica gel/toluene). The stability of 3 in solution is considerably higher than that of 4. The mu-oxo-bridged phthalocyanine dimers 3 and 4 have a more intense photoluminescence emission in the red region than the monomers 1 and 2. The gallium phthalocyanines 1 and 3 have fluorescence lifetimes of a few nanoseconds, while those of the indium phthalocyanines 2 and 4 last for only several hundred picoseconds. Comparison of the fluorescence lifetimes of monomers 1 and 3 with dimers 2 and 4, reveals that the dimers have longer lifetimes of the excited singlet states. The transient absorption spectrum is similar for all of the compounds, and the transient absorption band at about 520 nm, observed by nanosecond laser irradiation, can be assigned to the transition from the lowest triplet excited state to the upper triplet excited states (T-T absorption). The magnitude of the optical limiting exhibited by 1, 2, 3, and 4 in toluene at 532 nm laser pulse irradiation is in the order: 4>3>2>1 [corrected]. The values of the imaginary third-order nonlinear susceptibility Im[chi((3))] of the above compounds at 532 nm in toluene are also reported. These results demonstrate that these compounds are candidates for optical limiting applications.
DOI: 10.1002/1521-3765(20020916)8:18<4248::AID-CHEM4248>3.0.CO;2-R
PubMed: 12298016
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis and optical limiting properties of axially bridged phthalocyanines: [(tBu4PcGa)2O] and [(tBu4PcIn)2O].</title><author><name sortKey="Chen, Yu" uniqKey="Chen Y">Yu Chen</name><affiliation wicri:level="3"><nlm:affiliation>Institut für Organische Chemie, Organische Chemie II Universität Tübingen Auf der Morgenstelle 18, 72076 Tübingen, Germany.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>Institut für Organische Chemie, Organische Chemie II Universität Tübingen Auf der Morgenstelle 18, 72076 Tübingen</wicri:regionArea><placeName><region type="land" nuts="1">Bade-Wurtemberg</region><region type="district" nuts="2">District de Tübingen</region><settlement type="city">Tübingen</settlement></placeName></affiliation></author><author><name sortKey="Subramanian, L R" uniqKey="Subramanian L">L R Subramanian</name></author><author><name sortKey="Fujitsuka, Mamoru" uniqKey="Fujitsuka M">Mamoru Fujitsuka</name></author><author><name sortKey="Ito, Osamu" uniqKey="Ito O">Osamu Ito</name></author><author><name sortKey="O Flaherty, Sean" uniqKey="O Flaherty S">Sean O'Flaherty</name></author><author><name sortKey="Blau, Werner J" uniqKey="Blau W">Werner J Blau</name></author><author><name sortKey="Schneider, Thorsten" uniqKey="Schneider T">Thorsten Schneider</name></author><author><name sortKey="Dini, Danilo" uniqKey="Dini D">Danilo Dini</name></author><author><name sortKey="Hanack, Michael" uniqKey="Hanack M">Michael Hanack</name></author></titleStmt><publicationStmt><date when="2002">2002</date><idno type="RBID">pubmed:12298016</idno><idno type="pmid">12298016</idno><idno type="doi">10.1002/1521-3765(20020916)8:18<4248::AID-CHEM4248>3.0.CO;2-R</idno><idno type="wicri:Area/Main/Corpus">003659</idno><idno type="wicri:Area/Main/Curation">003659</idno><idno type="wicri:Area/Main/Exploration">003442</idno></publicationStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Highly soluble [(tBu(4)PcM)(2)O] phthalocyanine dimers (M=Ga(III) (3), In(III) (4)) were prepared by the reaction of [tBu(4)PcMCl] (M=Ga(III) (1), In(III) (2)) with excess of concentrated H(2)SO(4) at -20 degrees C. The Mbond;Obond;M linkages in 3 and 4 are not stable against concentrated H(2)SO(4) at room temperature, 6 n HCl at reflux, or during isolation under column chromatographic conditions (e.g. silica gel/toluene). The stability of 3 in solution is considerably higher than that of 4. The mu-oxo-bridged phthalocyanine dimers 3 and 4 have a more intense photoluminescence emission in the red region than the monomers 1 and 2. The gallium phthalocyanines 1 and 3 have fluorescence lifetimes of a few nanoseconds, while those of the indium phthalocyanines 2 and 4 last for only several hundred picoseconds. Comparison of the fluorescence lifetimes of monomers 1 and 3 with dimers 2 and 4, reveals that the dimers have longer lifetimes of the excited singlet states. The transient absorption spectrum is similar for all of the compounds, and the transient absorption band at about 520 nm, observed by nanosecond laser irradiation, can be assigned to the transition from the lowest triplet excited state to the upper triplet excited states (T-T absorption). The magnitude of the optical limiting exhibited by 1, 2, 3, and 4 in toluene at 532 nm laser pulse irradiation is in the order: 4>3>2>1 [corrected]. The values of the imaginary third-order nonlinear susceptibility Im[chi((3))] of the above compounds at 532 nm in toluene are also reported. These results demonstrate that these compounds are candidates for optical limiting applications.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="PubMed-not-MEDLINE"><PMID Version="1">12298016</PMID><DateCreated><Year>2002</Year><Month>09</Month><Day>25</Day></DateCreated><DateCompleted><Year>2003</Year><Month>01</Month><Day>27</Day></DateCompleted><DateRevised><Year>2009</Year><Month>08</Month><Day>04</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0947-6539</ISSN><JournalIssue CitedMedium="Print"><Volume>8</Volume><Issue>18</Issue><PubDate><Year>2002</Year><Month>Sep</Month><Day>16</Day></PubDate></JournalIssue><Title>Chemistry (Weinheim an der Bergstrasse, Germany)</Title><ISOAbbreviation>Chemistry</ISOAbbreviation></Journal><ArticleTitle>Synthesis and optical limiting properties of axially bridged phthalocyanines: [(tBu4PcGa)2O] and [(tBu4PcIn)2O].</ArticleTitle><Pagination><MedlinePgn>4248-54</MedlinePgn></Pagination><Abstract><AbstractText>Highly soluble [(tBu(4)PcM)(2)O] phthalocyanine dimers (M=Ga(III) (3), In(III) (4)) were prepared by the reaction of [tBu(4)PcMCl] (M=Ga(III) (1), In(III) (2)) with excess of concentrated H(2)SO(4) at -20 degrees C. The Mbond;Obond;M linkages in 3 and 4 are not stable against concentrated H(2)SO(4) at room temperature, 6 n HCl at reflux, or during isolation under column chromatographic conditions (e.g. silica gel/toluene). The stability of 3 in solution is considerably higher than that of 4. The mu-oxo-bridged phthalocyanine dimers 3 and 4 have a more intense photoluminescence emission in the red region than the monomers 1 and 2. The gallium phthalocyanines 1 and 3 have fluorescence lifetimes of a few nanoseconds, while those of the indium phthalocyanines 2 and 4 last for only several hundred picoseconds. Comparison of the fluorescence lifetimes of monomers 1 and 3 with dimers 2 and 4, reveals that the dimers have longer lifetimes of the excited singlet states. The transient absorption spectrum is similar for all of the compounds, and the transient absorption band at about 520 nm, observed by nanosecond laser irradiation, can be assigned to the transition from the lowest triplet excited state to the upper triplet excited states (T-T absorption). The magnitude of the optical limiting exhibited by 1, 2, 3, and 4 in toluene at 532 nm laser pulse irradiation is in the order: 4>3>2>1 [corrected]. The values of the imaginary third-order nonlinear susceptibility Im[chi((3))] of the above compounds at 532 nm in toluene are also reported. These results demonstrate that these compounds are candidates for optical limiting applications.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Chen</LastName><ForeName>Yu</ForeName><Initials>Y</Initials><Affiliation>Institut für Organische Chemie, Organische Chemie II Universität Tübingen Auf der Morgenstelle 18, 72076 Tübingen, Germany.</Affiliation></Author><Author ValidYN="Y"><LastName>Subramanian</LastName><ForeName>L R</ForeName><Initials>LR</Initials></Author><Author ValidYN="Y"><LastName>Fujitsuka</LastName><ForeName>Mamoru</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Ito</LastName><ForeName>Osamu</ForeName><Initials>O</Initials></Author><Author ValidYN="Y"><LastName>O'Flaherty</LastName><ForeName>Sean</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Blau</LastName><ForeName>Werner J</ForeName><Initials>WJ</Initials></Author><Author ValidYN="Y"><LastName>Schneider</LastName><ForeName>Thorsten</ForeName><Initials>T</Initials></Author><Author ValidYN="Y"><LastName>Dini</LastName><ForeName>Danilo</ForeName><Initials>D</Initials></Author><Author ValidYN="Y"><LastName>Hanack</LastName><ForeName>Michael</ForeName><Initials>M</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType>Journal Article</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>Chemistry</MedlineTA><NlmUniqueID>9513783</NlmUniqueID><ISSNLinking>0947-6539</ISSNLinking></MedlineJournalInfo><CommentsCorrectionsList><CommentsCorrections RefType="ErratumIn"><RefSource>Chemistry. 2002 Nov 4;8(21):4829</RefSource></CommentsCorrections></CommentsCorrectionsList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2002</Year><Month>9</Month><Day>26</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2002</Year><Month>9</Month><Day>26</Day><Hour>6</Hour><Minute>1</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2002</Year><Month>9</Month><Day>26</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">12298016</ArticleId><ArticleId IdType="doi">10.1002/1521-3765(20020916)8:18<4248::AID-CHEM4248>3.0.CO;2-R</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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