Structural Engineering of Luminogens with High Emission Efficiency Both in Solution and in the Solid State
Developing molecules with high emission efficiency both in solution and the solid state is still a great challenge, since most organic luminogens are either aggregation‐caused quenching or aggregation‐induced emission molecules. This dilemma was overcome by integrating planar and distorted structure...
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Veröffentlicht in: | Angewandte Chemie International Edition 2019-08, Vol.58 (33), p.11419-11423 |
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container_title | Angewandte Chemie International Edition |
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creator | Wu, Hongwei Chen, Zhao Chi, Weijie Bindra, Anivind Kaur Gu, Long Qian, Cheng Wu, Bing Yue, Bingbing Liu, Guofeng Yang, Guangbao Zhu, Liangliang Zhao, Yanli |
description | Developing molecules with high emission efficiency both in solution and the solid state is still a great challenge, since most organic luminogens are either aggregation‐caused quenching or aggregation‐induced emission molecules. This dilemma was overcome by integrating planar and distorted structures with long alkyl side chains to achieve DAπAD type emitters. A linear diphenyl–diacetylene core and the charge transfer effect ensure considerable planarity of these molecules in the excited state, allowing strong emission in dilute solution (quantum yield up to 98.2 %). On the other hand, intermolecular interactions of two distorted cyanostilbene units restrict molecular vibration and rotation, and long alkyl chains reduce the quenching effect of the π–π stacking to the excimer, eventually leading to strong emission in the solid state (quantum yield up to 60.7 %).
The integration of planar and distorted structures with long alkyl side chains to obtain molecules with high emission efficiency both in solution and the solid state is demonstrated. Efficient intracellular bioimaging using the molecules with different concentrations demonstrates the possibility of applying the highly emissive systems. |
doi_str_mv | 10.1002/anie.201906507 |
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The integration of planar and distorted structures with long alkyl side chains to obtain molecules with high emission efficiency both in solution and the solid state is demonstrated. Efficient intracellular bioimaging using the molecules with different concentrations demonstrates the possibility of applying the highly emissive systems.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201906507</identifier><identifier>PMID: 31206936</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Agglomeration ; bioimaging ; Chains ; Charge transfer ; Emission ; Emitters ; Excimers ; luminescence ; molecular engineering ; molecular stacking ; noncovalent interactions ; Quenching ; Solid state ; Structural engineering ; Vibration</subject><ispartof>Angewandte Chemie International Edition, 2019-08, Vol.58 (33), p.11419-11423</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4507-f00282b8359d6cfb8c858e05dc372b43ede3d8ea63c99f964f05f8c1ab87602d3</citedby><cites>FETCH-LOGICAL-c4507-f00282b8359d6cfb8c858e05dc372b43ede3d8ea63c99f964f05f8c1ab87602d3</cites><orcidid>0000-0002-9231-8360</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.201906507$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201906507$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31206936$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wu, Hongwei</creatorcontrib><creatorcontrib>Chen, Zhao</creatorcontrib><creatorcontrib>Chi, Weijie</creatorcontrib><creatorcontrib>Bindra, Anivind Kaur</creatorcontrib><creatorcontrib>Gu, Long</creatorcontrib><creatorcontrib>Qian, Cheng</creatorcontrib><creatorcontrib>Wu, Bing</creatorcontrib><creatorcontrib>Yue, Bingbing</creatorcontrib><creatorcontrib>Liu, Guofeng</creatorcontrib><creatorcontrib>Yang, Guangbao</creatorcontrib><creatorcontrib>Zhu, Liangliang</creatorcontrib><creatorcontrib>Zhao, Yanli</creatorcontrib><title>Structural Engineering of Luminogens with High Emission Efficiency Both in Solution and in the Solid State</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Developing molecules with high emission efficiency both in solution and the solid state is still a great challenge, since most organic luminogens are either aggregation‐caused quenching or aggregation‐induced emission molecules. This dilemma was overcome by integrating planar and distorted structures with long alkyl side chains to achieve DAπAD type emitters. A linear diphenyl–diacetylene core and the charge transfer effect ensure considerable planarity of these molecules in the excited state, allowing strong emission in dilute solution (quantum yield up to 98.2 %). On the other hand, intermolecular interactions of two distorted cyanostilbene units restrict molecular vibration and rotation, and long alkyl chains reduce the quenching effect of the π–π stacking to the excimer, eventually leading to strong emission in the solid state (quantum yield up to 60.7 %).
The integration of planar and distorted structures with long alkyl side chains to obtain molecules with high emission efficiency both in solution and the solid state is demonstrated. Efficient intracellular bioimaging using the molecules with different concentrations demonstrates the possibility of applying the highly emissive systems.</description><subject>Agglomeration</subject><subject>bioimaging</subject><subject>Chains</subject><subject>Charge transfer</subject><subject>Emission</subject><subject>Emitters</subject><subject>Excimers</subject><subject>luminescence</subject><subject>molecular engineering</subject><subject>molecular stacking</subject><subject>noncovalent interactions</subject><subject>Quenching</subject><subject>Solid state</subject><subject>Structural engineering</subject><subject>Vibration</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkb1v2zAQxYmiRZOmXTsWBLp0kcMPiaJG11DrAEY6OJkFijraNGTSJSUY_u9DwYkDZMnE493vHh75EPpOyYwSwm6VszBjhFZEFKT8gK5pwWjGy5J_THXOeVbKgl6hLzHuEi8lEZ_RFaeMiIqLa7RbD2HUwxhUj2u3sQ4gWLfB3uDVuLfOb8BFfLTDFi_tZovrvY3ReodrY6y24PQJ__Zpah1e-34cpply3XQftjD1bIfXgxrgK_pkVB_h2_N5gx7_1A-LZbb69_duMV9lOk9PyMxkk7WSF1UntGmlloUEUnSal6zNOXTAOwlKcF1VphK5IYWRmqpWloKwjt-gX2fdQ_D_R4hDkzxr6HvlwI-xYSxnkpayzBP68w2682NwyV2ihGSSEMITNTtTOvgYA5jmEOxehVNDSTOl0EwpNJcU0sKPZ9mx3UN3wV--PQHVGTjaHk7vyDXz-7v6VfwJZWWTeQ</recordid><startdate>20190812</startdate><enddate>20190812</enddate><creator>Wu, Hongwei</creator><creator>Chen, Zhao</creator><creator>Chi, Weijie</creator><creator>Bindra, Anivind Kaur</creator><creator>Gu, Long</creator><creator>Qian, Cheng</creator><creator>Wu, Bing</creator><creator>Yue, Bingbing</creator><creator>Liu, Guofeng</creator><creator>Yang, Guangbao</creator><creator>Zhu, Liangliang</creator><creator>Zhao, Yanli</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/0000-0002-9231-8360</orcidid></search><sort><creationdate>20190812</creationdate><title>Structural Engineering of Luminogens with High Emission Efficiency Both in Solution and in the Solid State</title><author>Wu, Hongwei ; Chen, Zhao ; Chi, Weijie ; Bindra, Anivind Kaur ; Gu, Long ; Qian, Cheng ; Wu, Bing ; Yue, Bingbing ; Liu, Guofeng ; Yang, Guangbao ; Zhu, Liangliang ; Zhao, Yanli</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4507-f00282b8359d6cfb8c858e05dc372b43ede3d8ea63c99f964f05f8c1ab87602d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Agglomeration</topic><topic>bioimaging</topic><topic>Chains</topic><topic>Charge transfer</topic><topic>Emission</topic><topic>Emitters</topic><topic>Excimers</topic><topic>luminescence</topic><topic>molecular engineering</topic><topic>molecular stacking</topic><topic>noncovalent interactions</topic><topic>Quenching</topic><topic>Solid state</topic><topic>Structural engineering</topic><topic>Vibration</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, Hongwei</creatorcontrib><creatorcontrib>Chen, Zhao</creatorcontrib><creatorcontrib>Chi, Weijie</creatorcontrib><creatorcontrib>Bindra, Anivind Kaur</creatorcontrib><creatorcontrib>Gu, Long</creatorcontrib><creatorcontrib>Qian, Cheng</creatorcontrib><creatorcontrib>Wu, Bing</creatorcontrib><creatorcontrib>Yue, Bingbing</creatorcontrib><creatorcontrib>Liu, Guofeng</creatorcontrib><creatorcontrib>Yang, Guangbao</creatorcontrib><creatorcontrib>Zhu, Liangliang</creatorcontrib><creatorcontrib>Zhao, Yanli</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>Wu, Hongwei</au><au>Chen, Zhao</au><au>Chi, Weijie</au><au>Bindra, Anivind Kaur</au><au>Gu, Long</au><au>Qian, Cheng</au><au>Wu, Bing</au><au>Yue, Bingbing</au><au>Liu, Guofeng</au><au>Yang, Guangbao</au><au>Zhu, Liangliang</au><au>Zhao, Yanli</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structural Engineering of Luminogens with High Emission Efficiency Both in Solution and in the Solid State</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2019-08-12</date><risdate>2019</risdate><volume>58</volume><issue>33</issue><spage>11419</spage><epage>11423</epage><pages>11419-11423</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Developing molecules with high emission efficiency both in solution and the solid state is still a great challenge, since most organic luminogens are either aggregation‐caused quenching or aggregation‐induced emission molecules. This dilemma was overcome by integrating planar and distorted structures with long alkyl side chains to achieve DAπAD type emitters. A linear diphenyl–diacetylene core and the charge transfer effect ensure considerable planarity of these molecules in the excited state, allowing strong emission in dilute solution (quantum yield up to 98.2 %). On the other hand, intermolecular interactions of two distorted cyanostilbene units restrict molecular vibration and rotation, and long alkyl chains reduce the quenching effect of the π–π stacking to the excimer, eventually leading to strong emission in the solid state (quantum yield up to 60.7 %).
The integration of planar and distorted structures with long alkyl side chains to obtain molecules with high emission efficiency both in solution and the solid state is demonstrated. Efficient intracellular bioimaging using the molecules with different concentrations demonstrates the possibility of applying the highly emissive systems.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31206936</pmid><doi>10.1002/anie.201906507</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-9231-8360</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | Agglomeration bioimaging Chains Charge transfer Emission Emitters Excimers luminescence molecular engineering molecular stacking noncovalent interactions Quenching Solid state Structural engineering Vibration |
title | Structural Engineering of Luminogens with High Emission Efficiency Both in Solution and in the Solid State |
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