Tetra(peri‐naphthylene)anthracene: A Near‐IR Fluorophore with Four‐Stage Amphoteric Redox Properties
A novel, benign synthetic strategy towards soluble tetra(peri‐naphthylene)anthracene (TPNA) decorated with triisopropylsilylethynyl substituents has been established. The compound is perfectly stable under ambient conditions in air and features intense and strongly bathochromically shifted UV/vis ab...
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Veröffentlicht in: | Chemistry : a European journal 2023-01, Vol.29 (6), p.e202203101-n/a |
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creator | Frisch, Sabine Neiß, Christian Lindenthal, Sebastian Zorn, Nicolas F. Rominger, Frank Görling, Andreas Zaumseil, Jana Kivala, Milan |
description | A novel, benign synthetic strategy towards soluble tetra(peri‐naphthylene)anthracene (TPNA) decorated with triisopropylsilylethynyl substituents has been established. The compound is perfectly stable under ambient conditions in air and features intense and strongly bathochromically shifted UV/vis absorption and emission bands reaching to near‐IR region beyond 900 nm. Cyclic voltammetry measurements revealed four facilitated reversible redox events comprising two oxidations and two reductions. These remarkable experimental findings were corroborated by theoretical studies to identify the TPNA platform a particularly useful candidate for the development of functional near‐IR fluorophores upon appropriate functionalization.
Towards the red‐light area. A reliable synthesis of a new tetra(peri‐naphthylene)anthracene derivative decorated with triisopropylsilylethynyl moieties has been established. The soluble compound features strongly bathochromically shifted absorption and emission bands reaching into the near‐IR region and is prone to four facilitated redox steps. The experimental results, corroborated by theoretical studies, identified the π‐conjugated polycyclic scaffold as a particularly promising candidate for the development of redox‐active near‐IR fluorophores. |
doi_str_mv | 10.1002/chem.202203101 |
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Towards the red‐light area. A reliable synthesis of a new tetra(peri‐naphthylene)anthracene derivative decorated with triisopropylsilylethynyl moieties has been established. The soluble compound features strongly bathochromically shifted absorption and emission bands reaching into the near‐IR region and is prone to four facilitated redox steps. The experimental results, corroborated by theoretical studies, identified the π‐conjugated polycyclic scaffold as a particularly promising candidate for the development of redox‐active near‐IR fluorophores.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202203101</identifier><identifier>PMID: 36287191</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Anthracene ; Chemical compounds ; Chemistry ; chromophores ; cyclopentannulation ; Fluorophores ; near-IR fluorophores ; polycycles ; redox amphoteric compounds ; Redox properties</subject><ispartof>Chemistry : a European journal, 2023-01, Vol.29 (6), p.e202203101-n/a</ispartof><rights>2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH</rights><rights>2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.</rights><rights>2022. This article is published under http://creativecommons.org/licenses/by-nc-nd/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-c4691-d7f4136d0f3e7a74ed052c6a75719bdc0ce52c3d51d5f42d451bdd32d024629b3</citedby><cites>FETCH-LOGICAL-c4691-d7f4136d0f3e7a74ed052c6a75719bdc0ce52c3d51d5f42d451bdd32d024629b3</cites><orcidid>0000-0002-4960-4636</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%2Fchem.202203101$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202203101$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,780,784,885,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36287191$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Frisch, Sabine</creatorcontrib><creatorcontrib>Neiß, Christian</creatorcontrib><creatorcontrib>Lindenthal, Sebastian</creatorcontrib><creatorcontrib>Zorn, Nicolas F.</creatorcontrib><creatorcontrib>Rominger, Frank</creatorcontrib><creatorcontrib>Görling, Andreas</creatorcontrib><creatorcontrib>Zaumseil, Jana</creatorcontrib><creatorcontrib>Kivala, Milan</creatorcontrib><title>Tetra(peri‐naphthylene)anthracene: A Near‐IR Fluorophore with Four‐Stage Amphoteric Redox Properties</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>A novel, benign synthetic strategy towards soluble tetra(peri‐naphthylene)anthracene (TPNA) decorated with triisopropylsilylethynyl substituents has been established. The compound is perfectly stable under ambient conditions in air and features intense and strongly bathochromically shifted UV/vis absorption and emission bands reaching to near‐IR region beyond 900 nm. Cyclic voltammetry measurements revealed four facilitated reversible redox events comprising two oxidations and two reductions. These remarkable experimental findings were corroborated by theoretical studies to identify the TPNA platform a particularly useful candidate for the development of functional near‐IR fluorophores upon appropriate functionalization.
Towards the red‐light area. A reliable synthesis of a new tetra(peri‐naphthylene)anthracene derivative decorated with triisopropylsilylethynyl moieties has been established. The soluble compound features strongly bathochromically shifted absorption and emission bands reaching into the near‐IR region and is prone to four facilitated redox steps. The experimental results, corroborated by theoretical studies, identified the π‐conjugated polycyclic scaffold as a particularly promising candidate for the development of redox‐active near‐IR fluorophores.</description><subject>Anthracene</subject><subject>Chemical compounds</subject><subject>Chemistry</subject><subject>chromophores</subject><subject>cyclopentannulation</subject><subject>Fluorophores</subject><subject>near-IR fluorophores</subject><subject>polycycles</subject><subject>redox amphoteric compounds</subject><subject>Redox properties</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFkUtv1DAUhS0EokNhyxJFYlMWGfx2zQaNRh1aqTxUytry2DdNRkkc7IQyO34Cv5FfgkdThseGlW2dz0f33IPQU4LnBGP60tXQzSmmFDOCyT00I4KSkikp7qMZ1lyVUjB9hB6ltMEYa8nYQ3TEJD1VRJMZ2lzDGO3JALH58e17b4d6rLct9PDC9mMdrcvXV8WieAc2ZuDiqli1U4hhqEOE4rYZ62IVpp30cbQ3UCy6rIzZzRVX4MPX4kNmIY4NpMfoQWXbBE_uzmP0aXV2vTwvL9-_uVguLkvHpSalVxUnTHpcMVBWcfBYUCetEnnitXfYQX4zL4gXFaeeC7L2nlGPKZdUr9kxer33HaZ1Bz4nyAlbM8Sms3Frgm3M30rf1OYmfDF5gVjJU5kdTu4cYvg8QRpN1yQHbWt7CFMyVFGNqdJ6hz7_B93kdfQ5X6YUU1wIxTM131MuhpQiVIdpCDa7Hs2uR3PoMX949meGA_6ruAzoPXDbtLD9j51Znp-9_W3-E0ctrgY</recordid><startdate>20230127</startdate><enddate>20230127</enddate><creator>Frisch, Sabine</creator><creator>Neiß, Christian</creator><creator>Lindenthal, Sebastian</creator><creator>Zorn, Nicolas F.</creator><creator>Rominger, Frank</creator><creator>Görling, Andreas</creator><creator>Zaumseil, Jana</creator><creator>Kivala, Milan</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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-4960-4636</orcidid></search><sort><creationdate>20230127</creationdate><title>Tetra(peri‐naphthylene)anthracene: A Near‐IR Fluorophore with Four‐Stage Amphoteric Redox Properties</title><author>Frisch, Sabine ; Neiß, Christian ; Lindenthal, Sebastian ; Zorn, Nicolas F. ; Rominger, Frank ; Görling, Andreas ; Zaumseil, Jana ; Kivala, Milan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4691-d7f4136d0f3e7a74ed052c6a75719bdc0ce52c3d51d5f42d451bdd32d024629b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Anthracene</topic><topic>Chemical compounds</topic><topic>Chemistry</topic><topic>chromophores</topic><topic>cyclopentannulation</topic><topic>Fluorophores</topic><topic>near-IR fluorophores</topic><topic>polycycles</topic><topic>redox amphoteric compounds</topic><topic>Redox properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Frisch, Sabine</creatorcontrib><creatorcontrib>Neiß, Christian</creatorcontrib><creatorcontrib>Lindenthal, Sebastian</creatorcontrib><creatorcontrib>Zorn, Nicolas F.</creatorcontrib><creatorcontrib>Rominger, Frank</creatorcontrib><creatorcontrib>Görling, Andreas</creatorcontrib><creatorcontrib>Zaumseil, Jana</creatorcontrib><creatorcontrib>Kivala, Milan</creatorcontrib><collection>Wiley Online Library (Open Access Collection)</collection><collection>Wiley Online Library (Open Access Collection)</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Frisch, Sabine</au><au>Neiß, Christian</au><au>Lindenthal, Sebastian</au><au>Zorn, Nicolas F.</au><au>Rominger, Frank</au><au>Görling, Andreas</au><au>Zaumseil, Jana</au><au>Kivala, Milan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Tetra(peri‐naphthylene)anthracene: A Near‐IR Fluorophore with Four‐Stage Amphoteric Redox Properties</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2023-01-27</date><risdate>2023</risdate><volume>29</volume><issue>6</issue><spage>e202203101</spage><epage>n/a</epage><pages>e202203101-n/a</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>A novel, benign synthetic strategy towards soluble tetra(peri‐naphthylene)anthracene (TPNA) decorated with triisopropylsilylethynyl substituents has been established. The compound is perfectly stable under ambient conditions in air and features intense and strongly bathochromically shifted UV/vis absorption and emission bands reaching to near‐IR region beyond 900 nm. Cyclic voltammetry measurements revealed four facilitated reversible redox events comprising two oxidations and two reductions. These remarkable experimental findings were corroborated by theoretical studies to identify the TPNA platform a particularly useful candidate for the development of functional near‐IR fluorophores upon appropriate functionalization.
Towards the red‐light area. A reliable synthesis of a new tetra(peri‐naphthylene)anthracene derivative decorated with triisopropylsilylethynyl moieties has been established. The soluble compound features strongly bathochromically shifted absorption and emission bands reaching into the near‐IR region and is prone to four facilitated redox steps. The experimental results, corroborated by theoretical studies, identified the π‐conjugated polycyclic scaffold as a particularly promising candidate for the development of redox‐active near‐IR fluorophores.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>36287191</pmid><doi>10.1002/chem.202203101</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-4960-4636</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | Anthracene Chemical compounds Chemistry chromophores cyclopentannulation Fluorophores near-IR fluorophores polycycles redox amphoteric compounds Redox properties |
title | Tetra(peri‐naphthylene)anthracene: A Near‐IR Fluorophore with Four‐Stage Amphoteric Redox Properties |
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