Chiral cyclic []spirobifluorenylenes: carbon nanorings consisting of helically arranged quaterphenyl rods illustrating partial units of woven patterns
Chiral cyclic [ n ]spirobifluorenylenes consisting of helically arranged quaterphenyl rods, illustrating partial units of woven patterns, were designed and synthesized as a new family of carbon nanorings. The synthesis was accomplished by the Ni(0)-mediated Yamamoto-coupling of chiral spirobifluoren...
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| Veröffentlicht in: | Chemical science (Cambridge) 2020-09, Vol.11 (35), p.964-961 |
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| creator | Zhu, Kaige Kamochi, Kosuke Kodama, Takuya Tobisu, Mamoru Amaya, Toru |
| description | Chiral cyclic [
n
]spirobifluorenylenes consisting of helically arranged quaterphenyl rods, illustrating partial units of woven patterns, were designed and synthesized as a new family of carbon nanorings. The synthesis was accomplished by the Ni(0)-mediated Yamamoto-coupling of chiral spirobifluorene building blocks. The structures of the cyclic 3-, 4-, and 5-mers were determined by X-ray crystallographic analysis. These carbon nanorings exhibited a strong violet colored emission with high quantum yields in solution (95%, 93%, and 94% for 3-, 4-, and 5-mer, respectively). Other spectroscopic properties, including their chiroptical properties, were also investigated. The
g
-values for circularly polarized luminescence were found to be in the order of 10
−3
. Characteristic spiroconjugation induced by multiple ( 3) bifluorenyl units, for example the even-odd effect of the number of units in the matching of the signs of the orbitals, was also indicated by DFT calculations.
Chiral cyclic [
n
]spirobifluorenylenes consisting of helically arranged quaterphenyl rods, illustrating partial units of woven patterns, were designed and synthesized as a new family of carbon nanorings. |
| doi_str_mv | 10.1039/d0sc02452j |
| format | Article |
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n
]spirobifluorenylenes consisting of helically arranged quaterphenyl rods, illustrating partial units of woven patterns, were designed and synthesized as a new family of carbon nanorings. The synthesis was accomplished by the Ni(0)-mediated Yamamoto-coupling of chiral spirobifluorene building blocks. The structures of the cyclic 3-, 4-, and 5-mers were determined by X-ray crystallographic analysis. These carbon nanorings exhibited a strong violet colored emission with high quantum yields in solution (95%, 93%, and 94% for 3-, 4-, and 5-mer, respectively). Other spectroscopic properties, including their chiroptical properties, were also investigated. The
g
-values for circularly polarized luminescence were found to be in the order of 10
−3
. Characteristic spiroconjugation induced by multiple ( 3) bifluorenyl units, for example the even-odd effect of the number of units in the matching of the signs of the orbitals, was also indicated by DFT calculations.
Chiral cyclic [
n
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n
]spirobifluorenylenes consisting of helically arranged quaterphenyl rods, illustrating partial units of woven patterns, were designed and synthesized as a new family of carbon nanorings. The synthesis was accomplished by the Ni(0)-mediated Yamamoto-coupling of chiral spirobifluorene building blocks. The structures of the cyclic 3-, 4-, and 5-mers were determined by X-ray crystallographic analysis. These carbon nanorings exhibited a strong violet colored emission with high quantum yields in solution (95%, 93%, and 94% for 3-, 4-, and 5-mer, respectively). Other spectroscopic properties, including their chiroptical properties, were also investigated. The
g
-values for circularly polarized luminescence were found to be in the order of 10
−3
. Characteristic spiroconjugation induced by multiple ( 3) bifluorenyl units, for example the even-odd effect of the number of units in the matching of the signs of the orbitals, was also indicated by DFT calculations.
Chiral cyclic [
n
]spirobifluorenylenes consisting of helically arranged quaterphenyl rods, illustrating partial units of woven patterns, were designed and synthesized as a new family of carbon nanorings.</description><subject>Carbon</subject><subject>Chemistry</subject><subject>Circular polarization</subject><subject>Crystallography</subject><subject>Emission analysis</subject><subject>Rods</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kk2LFDEQhoMo7rLuxbsQ8SILo_nqdMeDILN-suBBPYmEdJKeyZBJelPdK_NH_L1mdpYRPViXFMnzvlWhCqHHlLyghKuXjoAlTDRscw-dMiLoQjZc3T_mjJygc4ANqcE5bVj7EJ1wQZRgTJ6iX8t1KCZiu7MxWPz9B4yh5D4Mcc7Fp130ycMrbE3pc8LJpFxCWgG2OUGAqeY4D3jtq9jEuMOmFJNW3uHr2Uy-jOu9By7ZAQ4xzjAVcysaTZlCrTunMMHe4me-8aleT1WV4BF6MJgI_vzuPEPf3r39uvywuPr8_uPyzdXCCtVOi65n_cAZpa0YbO8cM7TlTS-9lFw5YagVfUt8Y2UrvOxUx4hpjHVcmdYPSvAz9PrgO8791jvrU20w6rGErSk7nU3Qf7-ksNarfKM7KqnsWDV4fmdQ8vXsYdLbANbHaJLPM2jW8I4IRZSq6LN_0E2eS6rf00wI1vFOkbZSFwfKlgxQ_HBshhK9n7i-JF-WtxP_VOGnB7iAPXJ_NkKPbqjMk_8x_Decw7cw</recordid><startdate>20200921</startdate><enddate>20200921</enddate><creator>Zhu, Kaige</creator><creator>Kamochi, Kosuke</creator><creator>Kodama, Takuya</creator><creator>Tobisu, Mamoru</creator><creator>Amaya, Toru</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-8415-2225</orcidid><orcidid>https://orcid.org/0000-0001-8275-2393</orcidid><orcidid>https://orcid.org/0000-0002-7716-0630</orcidid></search><sort><creationdate>20200921</creationdate><title>Chiral cyclic []spirobifluorenylenes: carbon nanorings consisting of helically arranged quaterphenyl rods illustrating partial units of woven patterns</title><author>Zhu, Kaige ; Kamochi, Kosuke ; Kodama, Takuya ; Tobisu, Mamoru ; Amaya, Toru</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c497t-8b2bf321174fcbdd2a1735b6e6639d4a1c4b70e5c674e689820a5acd39a7ef943</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Carbon</topic><topic>Chemistry</topic><topic>Circular polarization</topic><topic>Crystallography</topic><topic>Emission analysis</topic><topic>Rods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhu, Kaige</creatorcontrib><creatorcontrib>Kamochi, Kosuke</creatorcontrib><creatorcontrib>Kodama, Takuya</creatorcontrib><creatorcontrib>Tobisu, Mamoru</creatorcontrib><creatorcontrib>Amaya, Toru</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhu, Kaige</au><au>Kamochi, Kosuke</au><au>Kodama, Takuya</au><au>Tobisu, Mamoru</au><au>Amaya, Toru</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral cyclic []spirobifluorenylenes: carbon nanorings consisting of helically arranged quaterphenyl rods illustrating partial units of woven patterns</atitle><jtitle>Chemical science (Cambridge)</jtitle><date>2020-09-21</date><risdate>2020</risdate><volume>11</volume><issue>35</issue><spage>964</spage><epage>961</epage><pages>964-961</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>Chiral cyclic [
n
]spirobifluorenylenes consisting of helically arranged quaterphenyl rods, illustrating partial units of woven patterns, were designed and synthesized as a new family of carbon nanorings. The synthesis was accomplished by the Ni(0)-mediated Yamamoto-coupling of chiral spirobifluorene building blocks. The structures of the cyclic 3-, 4-, and 5-mers were determined by X-ray crystallographic analysis. These carbon nanorings exhibited a strong violet colored emission with high quantum yields in solution (95%, 93%, and 94% for 3-, 4-, and 5-mer, respectively). Other spectroscopic properties, including their chiroptical properties, were also investigated. The
g
-values for circularly polarized luminescence were found to be in the order of 10
−3
. Characteristic spiroconjugation induced by multiple ( 3) bifluorenyl units, for example the even-odd effect of the number of units in the matching of the signs of the orbitals, was also indicated by DFT calculations.
Chiral cyclic [
n
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| ispartof | Chemical science (Cambridge), 2020-09, Vol.11 (35), p.964-961 |
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| language | eng |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| subjects | Carbon Chemistry Circular polarization Crystallography Emission analysis Rods |
| title | Chiral cyclic []spirobifluorenylenes: carbon nanorings consisting of helically arranged quaterphenyl rods illustrating partial units of woven patterns |
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