Remarkable effects of terminal groups and solvents on helical folding of o-phenylene oligomers.
Identifieur interne : 001D74 ( PubMed/Corpus ); précédent : 001D73; suivant : 001D75Remarkable effects of terminal groups and solvents on helical folding of o-phenylene oligomers.
Auteurs : Shinji Ando ; Eisuke Ohta ; Atsuko Kosaka ; Daisuke Hashizume ; Hiroyuki Koshino ; Takanori Fukushima ; Takuzo AidaSource :
- Journal of the American Chemical Society [ 1520-5126 ] ; 2012.
Abstract
Although o-phenylene oligomers (OP(n)R) made of dimethoxyphenylene units are thought to be intrinsically dynamic due to π-electronic repulsion, we show that they fold into a regular helical geometry in CH(3)CN when they carry terminal groups such as CH(3), CH(2)OH, Br, CO(2)Bn, and NO(2). We evaluated their helical inversion kinetics via optical resolution of long-chain oligomers (e.g. 16- and 24-mers) by chiral HPLC. OP(24)Br at 298 K shows a half-life for the optical activity of 5.5 h in CH(3)OH/water (7/3 v/v) and requires 34 h for complete racemization. The perfectly folded helical conformers of OP(n)R, unlike their imperfectly folded ones, are devoid of extended π-conjugation and show a cyclic voltammogram featuring reversible multistep oxidation waves.
DOI: 10.1021/ja303117z
PubMed: 22709395
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We evaluated their helical inversion kinetics via optical resolution of long-chain oligomers (e.g. 16- and 24-mers) by chiral HPLC. OP(24)Br at 298 K shows a half-life for the optical activity of 5.5 h in CH(3)OH/water (7/3 v/v) and requires 34 h for complete racemization. The perfectly folded helical conformers of OP(n)R, unlike their imperfectly folded ones, are devoid of extended π-conjugation and show a cyclic voltammogram featuring reversible multistep oxidation waves.</div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">22709395</PMID><DateCompleted><Year>2012</Year><Month>11</Month><Day>05</Day></DateCompleted><DateRevised><Year>2012</Year><Month>07</Month><Day>11</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-5126</ISSN><JournalIssue CitedMedium="Internet"><Volume>134</Volume><Issue>27</Issue><PubDate><Year>2012</Year><Month>Jul</Month><Day>11</Day></PubDate></JournalIssue><Title>Journal of the American Chemical Society</Title><ISOAbbreviation>J. Am. Chem. Soc.</ISOAbbreviation></Journal><ArticleTitle>Remarkable effects of terminal groups and solvents on helical folding of o-phenylene oligomers.</ArticleTitle><Pagination><MedlinePgn>11084-7</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/ja303117z</ELocationID><Abstract><AbstractText>Although o-phenylene oligomers (OP(n)R) made of dimethoxyphenylene units are thought to be intrinsically dynamic due to π-electronic repulsion, we show that they fold into a regular helical geometry in CH(3)CN when they carry terminal groups such as CH(3), CH(2)OH, Br, CO(2)Bn, and NO(2). We evaluated their helical inversion kinetics via optical resolution of long-chain oligomers (e.g. 16- and 24-mers) by chiral HPLC. OP(24)Br at 298 K shows a half-life for the optical activity of 5.5 h in CH(3)OH/water (7/3 v/v) and requires 34 h for complete racemization. The perfectly folded helical conformers of OP(n)R, unlike their imperfectly folded ones, are devoid of extended π-conjugation and show a cyclic voltammogram featuring reversible multistep oxidation waves.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Ando</LastName><ForeName>Shinji</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Ohta</LastName><ForeName>Eisuke</ForeName><Initials>E</Initials></Author><Author ValidYN="Y"><LastName>Kosaka</LastName><ForeName>Atsuko</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Hashizume</LastName><ForeName>Daisuke</ForeName><Initials>D</Initials></Author><Author ValidYN="Y"><LastName>Koshino</LastName><ForeName>Hiroyuki</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Fukushima</LastName><ForeName>Takanori</ForeName><Initials>T</Initials></Author><Author ValidYN="Y"><LastName>Aida</LastName><ForeName>Takuzo</ForeName><Initials>T</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2012</Year><Month>06</Month><Day>28</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Am Chem Soc</MedlineTA><NlmUniqueID>7503056</NlmUniqueID><ISSNLinking>0002-7863</ISSNLinking></MedlineJournalInfo></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2012</Year><Month>6</Month><Day>20</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2012</Year><Month>6</Month><Day>20</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2012</Year><Month>6</Month><Day>20</Day><Hour>6</Hour><Minute>1</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">22709395</ArticleId><ArticleId IdType="doi">10.1021/ja303117z</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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