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Anthracene‐Fused Oligo‐BODIPYs: A New Class of π‐Extended NIR‐Absorbing Materials
Large π‐conjugated systems are key in the area of molecular materials. Herein, we prepare via AuI‐catalyzed cyclization a series of fully π‐conjugated anthracene‐fused oligo‐BODIPYs. Their structural and optoelectronic properties were studied by several techniques, ranging from X‐ray, UV/Vis, and cy...
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Published in: | Angewandte Chemie International Edition 2023-01, Vol.62 (5), p.e202214543-n/a |
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description | Large π‐conjugated systems are key in the area of molecular materials. Herein, we prepare via AuI‐catalyzed cyclization a series of fully π‐conjugated anthracene‐fused oligo‐BODIPYs. Their structural and optoelectronic properties were studied by several techniques, ranging from X‐ray, UV/Vis, and cyclic voltammetry to transient absorption spectroscopy. As a complement, their electronic structures were explored by means of Density Functional Theory (DFT) calculations. Depending on the size and shape of the π‐conjugated skeleton, unique features—such as face‐to‐face supramolecular organization, NIR absorption and fluorescence as well as strong electron accepting character—were noted. All in all, the aforementioned features render them valuable for technological applications.
AuI‐catalyzed cyclization has been used to prepare a series of fully π‐conjugated anthracene‐fused oligo‐BODIPYs. The size and shape of the π‐conjugated skeleton determines the unique features of the compounds—such as their face‐to‐face supramolecular organization, NIR absorption and fluorescence as well as strong electron accepting character. |
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AuI‐catalyzed cyclization has been used to prepare a series of fully π‐conjugated anthracene‐fused oligo‐BODIPYs. The size and shape of the π‐conjugated skeleton determines the unique features of the compounds—such as their face‐to‐face supramolecular organization, NIR absorption and fluorescence as well as strong electron accepting character.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202214543</identifier><identifier>PMID: 36350769</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Absorption spectroscopy ; Anthracene ; BODIPY ; Conjugation ; Density functional theory ; Dyes/Pigments ; Fluorescence ; NIR ; Optoelectronics ; π-Systems</subject><ispartof>Angewandte Chemie International Edition, 2023-01, Vol.62 (5), p.e202214543-n/a</ispartof><rights>2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH</rights><rights>2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.</rights><rights>2022. This article is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4693-a51a91b25bf4cbfc67b658629d499c7067d3fcfa7704b48b04c7f15adc775e103</citedby><cites>FETCH-LOGICAL-c4693-a51a91b25bf4cbfc67b658629d499c7067d3fcfa7704b48b04c7f15adc775e103</cites><orcidid>0000-0002-3960-1765 ; 0000-0001-9335-6935 ; 0000-0001-5665-2778 ; 0000-0001-8502-288X</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.202214543$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202214543$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,315,786,790,891,27957,27958,50923,51032</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36350769$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Labella, Jorge</creatorcontrib><creatorcontrib>Durán‐Sampedro, Gonzalo</creatorcontrib><creatorcontrib>Krishna, Swathi</creatorcontrib><creatorcontrib>Martínez‐Díaz, M. Victoria</creatorcontrib><creatorcontrib>Guldi, Dirk M.</creatorcontrib><creatorcontrib>Torres, Tomás</creatorcontrib><title>Anthracene‐Fused Oligo‐BODIPYs: A New Class of π‐Extended NIR‐Absorbing Materials</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Large π‐conjugated systems are key in the area of molecular materials. Herein, we prepare via AuI‐catalyzed cyclization a series of fully π‐conjugated anthracene‐fused oligo‐BODIPYs. Their structural and optoelectronic properties were studied by several techniques, ranging from X‐ray, UV/Vis, and cyclic voltammetry to transient absorption spectroscopy. As a complement, their electronic structures were explored by means of Density Functional Theory (DFT) calculations. Depending on the size and shape of the π‐conjugated skeleton, unique features—such as face‐to‐face supramolecular organization, NIR absorption and fluorescence as well as strong electron accepting character—were noted. All in all, the aforementioned features render them valuable for technological applications.
AuI‐catalyzed cyclization has been used to prepare a series of fully π‐conjugated anthracene‐fused oligo‐BODIPYs. The size and shape of the π‐conjugated skeleton determines the unique features of the compounds—such as their face‐to‐face supramolecular organization, NIR absorption and fluorescence as well as strong electron accepting character.</description><subject>Absorption spectroscopy</subject><subject>Anthracene</subject><subject>BODIPY</subject><subject>Conjugation</subject><subject>Density functional theory</subject><subject>Dyes/Pigments</subject><subject>Fluorescence</subject><subject>NIR</subject><subject>Optoelectronics</subject><subject>π-Systems</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFkctu1DAUhi1ERW9sWaJIbNhk6rsTNigMUxipnakqWMDGsh1n6ioTFzvpZddH6JvxDjxJPZoypWy6OufofOfX-fUD8AbBEYIQH6jO2RGGGCPKKHkBdhDDKCdCkJepp4TkomBoG-zGeJ74ooD8FdgmnDAoeLkDflZdfxaUsZ39c3t3OERbZ_PWLXyaPs0_T09-xA9Zlc3sVTZuVYyZb7Lft2k5ue5tVyd6Nj1NY6WjD9p1i-xY9TY41cZ9sNWkYl8_1D3w_XDybfw1P5p_mY6ro9xQXpJcMaRKpDHTDTW6MVxozgqOy5qWpRGQi5o0plFCQKppoSE1okFM1UYIZhEke-DjWvdi0EtbJyt9UK28CG6pwo30ysmnm86dyYW_lAgiKLBYKbx_UAj-12BjL5cuGtu2qrN-iBILQjkimIiEvvsPPfdD6JK_RHFeUlRgkqjRmjLBxxhss_kGQbnKTa5yk5vc0sHbfz1s8L9BJaBcA1eutTfPyMlqNp08it8DPf-n1w</recordid><startdate>20230126</startdate><enddate>20230126</enddate><creator>Labella, Jorge</creator><creator>Durán‐Sampedro, Gonzalo</creator><creator>Krishna, Swathi</creator><creator>Martínez‐Díaz, M. Victoria</creator><creator>Guldi, Dirk M.</creator><creator>Torres, Tomás</creator><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>WIN</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-3960-1765</orcidid><orcidid>https://orcid.org/0000-0001-9335-6935</orcidid><orcidid>https://orcid.org/0000-0001-5665-2778</orcidid><orcidid>https://orcid.org/0000-0001-8502-288X</orcidid></search><sort><creationdate>20230126</creationdate><title>Anthracene‐Fused Oligo‐BODIPYs: A New Class of π‐Extended NIR‐Absorbing Materials</title><author>Labella, Jorge ; Durán‐Sampedro, Gonzalo ; Krishna, Swathi ; Martínez‐Díaz, M. 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Victoria</au><au>Guldi, Dirk M.</au><au>Torres, Tomás</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anthracene‐Fused Oligo‐BODIPYs: A New Class of π‐Extended NIR‐Absorbing Materials</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2023-01-26</date><risdate>2023</risdate><volume>62</volume><issue>5</issue><spage>e202214543</spage><epage>n/a</epage><pages>e202214543-n/a</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>Large π‐conjugated systems are key in the area of molecular materials. Herein, we prepare via AuI‐catalyzed cyclization a series of fully π‐conjugated anthracene‐fused oligo‐BODIPYs. 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AuI‐catalyzed cyclization has been used to prepare a series of fully π‐conjugated anthracene‐fused oligo‐BODIPYs. The size and shape of the π‐conjugated skeleton determines the unique features of the compounds—such as their face‐to‐face supramolecular organization, NIR absorption and fluorescence as well as strong electron accepting character.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>36350769</pmid><doi>10.1002/anie.202214543</doi><tpages>7</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-3960-1765</orcidid><orcidid>https://orcid.org/0000-0001-9335-6935</orcidid><orcidid>https://orcid.org/0000-0001-5665-2778</orcidid><orcidid>https://orcid.org/0000-0001-8502-288X</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | Absorption spectroscopy Anthracene BODIPY Conjugation Density functional theory Dyes/Pigments Fluorescence NIR Optoelectronics π-Systems |
title | Anthracene‐Fused Oligo‐BODIPYs: A New Class of π‐Extended NIR‐Absorbing Materials |
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