Conformational Dynamics of Monomer‐ versus Dimer‐like Features in a Naphthalenediimide‐Based Conjugated Cyclophane
The design and synthesis of an enantiomeric pair of 1,8‐diethynylanthracene‐bridged naphthalenediimide (NDI)‐based cyclophanes (Cyclo‐NDIs) are reported. Each enantiomer of Cyclo‐NDI exhibits a circularly polarized luminescence signal with a relatively large luminescence dissymmetry factor (glum=±8×...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2020-03, Vol.59 (13), p.5254-5258 |
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| creator | Keshri, Sudhir Kumar Takai, Atsuro Ishizuka, Tomoya Kojima, Takahiko Takeuchi, Masayuki |
| description | The design and synthesis of an enantiomeric pair of 1,8‐diethynylanthracene‐bridged naphthalenediimide (NDI)‐based cyclophanes (Cyclo‐NDIs) are reported. Each enantiomer of Cyclo‐NDI exhibits a circularly polarized luminescence signal with a relatively large luminescence dissymmetry factor (glum=±8×10−3). We have further investigated the modulation of through‐space electronic communication between co‐facially oriented NDIs in a discrete Cyclo‐NDI with changes in the temperature. Tuning of the electronic communication results from the conformational transformation of monomer‐ versus dimer‐like features of Cyclo‐NDI, as confirmed by UV/Vis, fluorescence, circular dichroic, and NMR spectroscopic analysis. The temperature‐dependent optical response in the Cyclo‐NDI through the conformational transformation could be utilized as a highly sensitive and reversible optical thermometer in a wide temperature range (100 to −80 °C).
A shining duo: A pair of conjugated cyclophane enantiomers, (+)‐ and (−)‐Cyclo‐NDIs, is reported. The spatial electronic communication between co‐facially oriented naphthalenediimide units in Cyclo‐NDI is modulated by external stimuli such as the temperature and solvent polarity, resulting in large optical changes. |
| doi_str_mv | 10.1002/anie.201914414 |
| format | Article |
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A shining duo: A pair of conjugated cyclophane enantiomers, (+)‐ and (−)‐Cyclo‐NDIs, is reported. The spatial electronic communication between co‐facially oriented naphthalenediimide units in Cyclo‐NDI is modulated by external stimuli such as the temperature and solvent polarity, resulting in large optical changes.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201914414</identifier><identifier>PMID: 31854072</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Circular polarization ; circularly polarized luminescence ; conformational transformations ; Cyclophane ; cyclophanes ; Dimers ; Enantiomers ; Fluorescence ; Luminescence ; Monomers ; naphthalenediimide dimers ; NMR ; Nuclear magnetic resonance ; optical thermometry ; Temperature dependence</subject><ispartof>Angewandte Chemie International Edition, 2020-03, Vol.59 (13), p.5254-5258</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4764-d0f5cb5a521d4ff4a75f5864ce53069a537ed259002694ffc0872152ec54cc183</citedby><cites>FETCH-LOGICAL-c4764-d0f5cb5a521d4ff4a75f5864ce53069a537ed259002694ffc0872152ec54cc183</cites><orcidid>0000-0002-7377-9305 ; 0000-0001-9941-8375 ; 0000-0003-3457-3352 ; 0000-0002-3897-026X ; 0000-0002-0207-0665</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201914414$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201914414$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31854072$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Keshri, Sudhir Kumar</creatorcontrib><creatorcontrib>Takai, Atsuro</creatorcontrib><creatorcontrib>Ishizuka, Tomoya</creatorcontrib><creatorcontrib>Kojima, Takahiko</creatorcontrib><creatorcontrib>Takeuchi, Masayuki</creatorcontrib><title>Conformational Dynamics of Monomer‐ versus Dimer‐like Features in a Naphthalenediimide‐Based Conjugated Cyclophane</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>The design and synthesis of an enantiomeric pair of 1,8‐diethynylanthracene‐bridged naphthalenediimide (NDI)‐based cyclophanes (Cyclo‐NDIs) are reported. Each enantiomer of Cyclo‐NDI exhibits a circularly polarized luminescence signal with a relatively large luminescence dissymmetry factor (glum=±8×10−3). We have further investigated the modulation of through‐space electronic communication between co‐facially oriented NDIs in a discrete Cyclo‐NDI with changes in the temperature. Tuning of the electronic communication results from the conformational transformation of monomer‐ versus dimer‐like features of Cyclo‐NDI, as confirmed by UV/Vis, fluorescence, circular dichroic, and NMR spectroscopic analysis. The temperature‐dependent optical response in the Cyclo‐NDI through the conformational transformation could be utilized as a highly sensitive and reversible optical thermometer in a wide temperature range (100 to −80 °C).
A shining duo: A pair of conjugated cyclophane enantiomers, (+)‐ and (−)‐Cyclo‐NDIs, is reported. The spatial electronic communication between co‐facially oriented naphthalenediimide units in Cyclo‐NDI is modulated by external stimuli such as the temperature and solvent polarity, resulting in large optical changes.</description><subject>Circular polarization</subject><subject>circularly polarized luminescence</subject><subject>conformational transformations</subject><subject>Cyclophane</subject><subject>cyclophanes</subject><subject>Dimers</subject><subject>Enantiomers</subject><subject>Fluorescence</subject><subject>Luminescence</subject><subject>Monomers</subject><subject>naphthalenediimide dimers</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>optical thermometry</subject><subject>Temperature dependence</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkblOxDAQhi0E4lhoKZElGposPuOkhOWUOBqoI-NMWC9JvNgJsB2PwDPyJHi1C0g0VDMjffPP8SO0S8mQEsIOdWthyAjNqRBUrKBNKhlNuFJ8NeaC80Rlkm6grRAmkc8ykq6jDU4zKYhim-ht5NrK-UZ31rW6xiezVjfWBOwqfO1a14D_fP_AL-BDH_CJXdS1fQJ8BrrrPQRsW6zxjZ6Ou7GuoYXS2saWELljHaDEccSkf9TdPJ2Z2k3HuoVttFbpOsDOMg7Q_dnp3egiubo9vxwdXSVGqFQkJamkeZA6XlWKqhJayUpmqTAgOUlzLbmCksk83pbmETAkUyz-AIwUxtCMD9DBQnfq3XMPoSsaGwzUddzB9aFgnGVKUpmmEd3_g05c7-NX5pRSTArBVKSGC8p4F4KHqph622g_Kygp5p4Uc0-KH09iw95Stn9ooPzBv02IQL4AXm0Ns3_kiqOby9Nf8S_Z95uh</recordid><startdate>20200323</startdate><enddate>20200323</enddate><creator>Keshri, Sudhir Kumar</creator><creator>Takai, Atsuro</creator><creator>Ishizuka, Tomoya</creator><creator>Kojima, Takahiko</creator><creator>Takeuchi, Masayuki</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7377-9305</orcidid><orcidid>https://orcid.org/0000-0001-9941-8375</orcidid><orcidid>https://orcid.org/0000-0003-3457-3352</orcidid><orcidid>https://orcid.org/0000-0002-3897-026X</orcidid><orcidid>https://orcid.org/0000-0002-0207-0665</orcidid></search><sort><creationdate>20200323</creationdate><title>Conformational Dynamics of Monomer‐ versus Dimer‐like Features in a Naphthalenediimide‐Based Conjugated Cyclophane</title><author>Keshri, Sudhir Kumar ; Takai, Atsuro ; Ishizuka, Tomoya ; Kojima, Takahiko ; Takeuchi, Masayuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4764-d0f5cb5a521d4ff4a75f5864ce53069a537ed259002694ffc0872152ec54cc183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Circular polarization</topic><topic>circularly polarized luminescence</topic><topic>conformational transformations</topic><topic>Cyclophane</topic><topic>cyclophanes</topic><topic>Dimers</topic><topic>Enantiomers</topic><topic>Fluorescence</topic><topic>Luminescence</topic><topic>Monomers</topic><topic>naphthalenediimide dimers</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>optical thermometry</topic><topic>Temperature dependence</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Keshri, Sudhir Kumar</creatorcontrib><creatorcontrib>Takai, Atsuro</creatorcontrib><creatorcontrib>Ishizuka, Tomoya</creatorcontrib><creatorcontrib>Kojima, Takahiko</creatorcontrib><creatorcontrib>Takeuchi, Masayuki</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Keshri, Sudhir Kumar</au><au>Takai, Atsuro</au><au>Ishizuka, Tomoya</au><au>Kojima, Takahiko</au><au>Takeuchi, Masayuki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Conformational Dynamics of Monomer‐ versus Dimer‐like Features in a Naphthalenediimide‐Based Conjugated Cyclophane</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2020-03-23</date><risdate>2020</risdate><volume>59</volume><issue>13</issue><spage>5254</spage><epage>5258</epage><pages>5254-5258</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The design and synthesis of an enantiomeric pair of 1,8‐diethynylanthracene‐bridged naphthalenediimide (NDI)‐based cyclophanes (Cyclo‐NDIs) are reported. Each enantiomer of Cyclo‐NDI exhibits a circularly polarized luminescence signal with a relatively large luminescence dissymmetry factor (glum=±8×10−3). We have further investigated the modulation of through‐space electronic communication between co‐facially oriented NDIs in a discrete Cyclo‐NDI with changes in the temperature. Tuning of the electronic communication results from the conformational transformation of monomer‐ versus dimer‐like features of Cyclo‐NDI, as confirmed by UV/Vis, fluorescence, circular dichroic, and NMR spectroscopic analysis. The temperature‐dependent optical response in the Cyclo‐NDI through the conformational transformation could be utilized as a highly sensitive and reversible optical thermometer in a wide temperature range (100 to −80 °C).
A shining duo: A pair of conjugated cyclophane enantiomers, (+)‐ and (−)‐Cyclo‐NDIs, is reported. The spatial electronic communication between co‐facially oriented naphthalenediimide units in Cyclo‐NDI is modulated by external stimuli such as the temperature and solvent polarity, resulting in large optical changes.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31854072</pmid><doi>10.1002/anie.201914414</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-7377-9305</orcidid><orcidid>https://orcid.org/0000-0001-9941-8375</orcidid><orcidid>https://orcid.org/0000-0003-3457-3352</orcidid><orcidid>https://orcid.org/0000-0002-3897-026X</orcidid><orcidid>https://orcid.org/0000-0002-0207-0665</orcidid></addata></record> |
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| subjects | Circular polarization circularly polarized luminescence conformational transformations Cyclophane cyclophanes Dimers Enantiomers Fluorescence Luminescence Monomers naphthalenediimide dimers NMR Nuclear magnetic resonance optical thermometry Temperature dependence |
| title | Conformational Dynamics of Monomer‐ versus Dimer‐like Features in a Naphthalenediimide‐Based Conjugated Cyclophane |
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