Highly blue luminescent triazine-amine conjugated oligomers.
Identifieur interne : 002300 ( PubMed/Curation ); précédent : 002299; suivant : 002301Highly blue luminescent triazine-amine conjugated oligomers.
Auteurs : Takashi Murase [Japon] ; Makoto FujitaSource :
- The Journal of organic chemistry [ 0022-3263 ] ; 2005.
Abstract
[Reaction: see text]. The novel synthetic strategy and optical properties of highly fluorescent, triazine-amine conjugated oligomers are described herein. Under basic conditions, aromatic dinitrile compounds, NC-C6H4-X-C6H4-CN (X = NMe, O, CH2), underwent cyclic trimerization of the cyano groups at both ends to give a series of triazine-containing oligomers. The oligomers can be expressed as (2n + 1) mer, where n represents the number of triazine rings in the oligomer. The absorption maximum of an amine-conjugated trimer (X = NMe, n = 1) was outstandingly red-shifted as compared with those of the other trimers (X = CH2, O). In acidic media, the amine-conjugated trimer showed two-step bathochromic shifts caused by protonation. The absorption maxima of the amine-conjugated (2n + 1) mers (X = NMe, n = 1-4) did not depend on n; instead, shoulder peaks appeared in the long-wavelength region when n 2. The oligomers involving alternate conjugation of triazines and NMe groups through phenylene groups showed strong fluorescence in chloroform. In particular, the pentamer was the most efficient blue emitter (PhiF = 0.82). The other triazine-containing oligomers (X = CH2, O) did not show fluorescence at all. Therefore, it is concluded that the emission properties are due to the strong electron-donating and accepting abilities of the NMe and triazine moieties, respectively.
DOI: 10.1021/jo051268h
PubMed: 16268599
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Highly blue luminescent triazine-amine conjugated oligomers.</title><author><name sortKey="Murase, Takashi" sort="Murase, Takashi" uniqKey="Murase T" first="Takashi" last="Murase">Takashi Murase</name><affiliation wicri:level="1"><nlm:affiliation>Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656</wicri:regionArea></affiliation></author><author><name sortKey="Fujita, Makoto" sort="Fujita, Makoto" uniqKey="Fujita M" first="Makoto" last="Fujita">Makoto Fujita</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2005">2005</date><idno type="RBID">pubmed:16268599</idno><idno type="pmid">16268599</idno><idno type="doi">10.1021/jo051268h</idno><idno type="wicri:Area/PubMed/Corpus">002300</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002300</idno><idno type="wicri:Area/PubMed/Curation">002300</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">002300</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Highly blue luminescent triazine-amine conjugated oligomers.</title><author><name sortKey="Murase, Takashi" sort="Murase, Takashi" uniqKey="Murase T" first="Takashi" last="Murase">Takashi Murase</name><affiliation wicri:level="1"><nlm:affiliation>Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656</wicri:regionArea></affiliation></author><author><name sortKey="Fujita, Makoto" sort="Fujita, Makoto" uniqKey="Fujita M" first="Makoto" last="Fujita">Makoto Fujita</name></author></analytic><series><title level="j">The Journal of organic chemistry</title><idno type="ISSN">0022-3263</idno><imprint><date when="2005" type="published">2005</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">[Reaction: see text]. The novel synthetic strategy and optical properties of highly fluorescent, triazine-amine conjugated oligomers are described herein. Under basic conditions, aromatic dinitrile compounds, NC-C6H4-X-C6H4-CN (X = NMe, O, CH2), underwent cyclic trimerization of the cyano groups at both ends to give a series of triazine-containing oligomers. The oligomers can be expressed as (2n + 1) mer, where n represents the number of triazine rings in the oligomer. The absorption maximum of an amine-conjugated trimer (X = NMe, n = 1) was outstandingly red-shifted as compared with those of the other trimers (X = CH2, O). In acidic media, the amine-conjugated trimer showed two-step bathochromic shifts caused by protonation. The absorption maxima of the amine-conjugated (2n + 1) mers (X = NMe, n = 1-4) did not depend on n; instead, shoulder peaks appeared in the long-wavelength region when n 2. The oligomers involving alternate conjugation of triazines and NMe groups through phenylene groups showed strong fluorescence in chloroform. In particular, the pentamer was the most efficient blue emitter (PhiF = 0.82). The other triazine-containing oligomers (X = CH2, O) did not show fluorescence at all. Therefore, it is concluded that the emission properties are due to the strong electron-donating and accepting abilities of the NMe and triazine moieties, respectively.</div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">16268599</PMID><DateCompleted><Year>2006</Year><Month>06</Month><Day>20</Day></DateCompleted><DateRevised><Year>2005</Year><Month>11</Month><Day>04</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0022-3263</ISSN><JournalIssue CitedMedium="Print"><Volume>70</Volume><Issue>23</Issue><PubDate><Year>2005</Year><Month>Nov</Month><Day>11</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>Highly blue luminescent triazine-amine conjugated oligomers.</ArticleTitle><Pagination><MedlinePgn>9269-78</MedlinePgn></Pagination><Abstract><AbstractText>[Reaction: see text]. The novel synthetic strategy and optical properties of highly fluorescent, triazine-amine conjugated oligomers are described herein. Under basic conditions, aromatic dinitrile compounds, NC-C6H4-X-C6H4-CN (X = NMe, O, CH2), underwent cyclic trimerization of the cyano groups at both ends to give a series of triazine-containing oligomers. The oligomers can be expressed as (2n + 1) mer, where n represents the number of triazine rings in the oligomer. The absorption maximum of an amine-conjugated trimer (X = NMe, n = 1) was outstandingly red-shifted as compared with those of the other trimers (X = CH2, O). In acidic media, the amine-conjugated trimer showed two-step bathochromic shifts caused by protonation. The absorption maxima of the amine-conjugated (2n + 1) mers (X = NMe, n = 1-4) did not depend on n; instead, shoulder peaks appeared in the long-wavelength region when n 2. The oligomers involving alternate conjugation of triazines and NMe groups through phenylene groups showed strong fluorescence in chloroform. In particular, the pentamer was the most efficient blue emitter (PhiF = 0.82). The other triazine-containing oligomers (X = CH2, O) did not show fluorescence at all. Therefore, it is concluded that the emission properties are due to the strong electron-donating and accepting abilities of the NMe and triazine moieties, respectively.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Murase</LastName><ForeName>Takashi</ForeName><Initials>T</Initials><AffiliationInfo><Affiliation>Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Fujita</LastName><ForeName>Makoto</ForeName><Initials>M</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Org Chem</MedlineTA><NlmUniqueID>2985193R</NlmUniqueID><ISSNLinking>0022-3263</ISSNLinking></MedlineJournalInfo></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2005</Year><Month>11</Month><Day>5</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2005</Year><Month>11</Month><Day>5</Day><Hour>9</Hour><Minute>1</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2005</Year><Month>11</Month><Day>5</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">16268599</ArticleId><ArticleId IdType="doi">10.1021/jo051268h</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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