Highly Emissive Far Red/Near-IR Fluorophores Based on Borylated Fluorene-Benzothiadiazole Donor-Acceptor Materials
Stille, Suzuki–Miyaura and Negishi cross‐coupling reactions of bromine‐functionalised borylated precursors enable the facile, high yielding, synthesis of borylated donor–acceptor materials that contain electron‐rich aromatic units and/or extended effective conjugation lengths. These materials have l...
Gespeichert in:
| Veröffentlicht in: | Chemistry : a European journal 2016-08, Vol.22 (35), p.12439-12448 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 12448 |
|---|---|
| container_issue | 35 |
| container_start_page | 12439 |
| container_title | Chemistry : a European journal |
| container_volume | 22 |
| creator | Crossley, Daniel L. Vitorica-Yrezabal, Inigo Humphries, Martin J. Turner, Michael L. Ingleson, Michael J. |
| description | Stille, Suzuki–Miyaura and Negishi cross‐coupling reactions of bromine‐functionalised borylated precursors enable the facile, high yielding, synthesis of borylated donor–acceptor materials that contain electron‐rich aromatic units and/or extended effective conjugation lengths. These materials have large Stokes shifts, low LUMO energies, small band‐gaps and significant fluorescence emission >700 nm in solution and when dispersed in a host polymer.
The perfect couple: Cross‐coupling enables the high yielding synthesis of borylated donor–acceptor materials that contain electron‐rich aromatics units and/or extended effective conjugation lengths. These materials have large Stokes shifts, low LUMO energies, small band‐gaps and significant fluorescence emission >700 nm in solution and in the solid state. |
| doi_str_mv | 10.1002/chem.201602010 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_6680280</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1811294140</sourcerecordid><originalsourceid>FETCH-LOGICAL-c6420-21413904030a170253356f4793ac72c936774a65124633055f071020790142cf3</originalsourceid><addsrcrecordid>eNqNkc1vEzEQxS0EoqFw5YhW4sJl0_F3fEFq0qSp1ASpKuJoGcfbddmsg71bSP96nKZEhQtcPLLmN08z7yH0FsMQA5ATW7v1kAAWkB94hgaYE1xSKfhzNADFZCk4VUfoVUq3AKAEpS_REZFMgBSjAYpzf1M322K69in5O1fMTCyu3Opk6UwsL66KWdOHGDZ1iC4VY5PcqghtMQ5x25gufx76rnXl2LX3oau9WXlzHxpXnIU2xPLUWrfpQiwWGY_eNOk1elHl4t481mP0eTa9nszLy0_nF5PTy9IKRqAkmGGqgAEFgyUQTikXFZOKGiuJVVRIyYzgmLB8FHBegcTZBakAM2Ireow-7nU3_de1W1nXdtE0ehP92sStDsbrPzutr_VNuNNCjICMIAt8eBSI4XvvUqezSdY1jWld6JPGI8o5ZxxG_4FiTBTDbKf6_i_0NvSxzU48UIpwIXbUcE_ZGFKKrjrsjUHvkte75PUh-Tzw7um1B_x31BlQe-CHb9z2H3J6Mp8unoqX-1mfOvfzMGviNy0klVx_WZ7rswmopVzM9TX9Bafkxyk</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1811925660</pqid></control><display><type>article</type><title>Highly Emissive Far Red/Near-IR Fluorophores Based on Borylated Fluorene-Benzothiadiazole Donor-Acceptor Materials</title><source>Access via Wiley Online Library</source><creator>Crossley, Daniel L. ; Vitorica-Yrezabal, Inigo ; Humphries, Martin J. ; Turner, Michael L. ; Ingleson, Michael J.</creator><creatorcontrib>Crossley, Daniel L. ; Vitorica-Yrezabal, Inigo ; Humphries, Martin J. ; Turner, Michael L. ; Ingleson, Michael J.</creatorcontrib><description>Stille, Suzuki–Miyaura and Negishi cross‐coupling reactions of bromine‐functionalised borylated precursors enable the facile, high yielding, synthesis of borylated donor–acceptor materials that contain electron‐rich aromatic units and/or extended effective conjugation lengths. These materials have large Stokes shifts, low LUMO energies, small band‐gaps and significant fluorescence emission >700 nm in solution and when dispersed in a host polymer.
The perfect couple: Cross‐coupling enables the high yielding synthesis of borylated donor–acceptor materials that contain electron‐rich aromatics units and/or extended effective conjugation lengths. These materials have large Stokes shifts, low LUMO energies, small band‐gaps and significant fluorescence emission >700 nm in solution and in the solid state.</description><identifier>ISSN: 0947-6539</identifier><identifier>ISSN: 1521-3765</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201602010</identifier><identifier>PMID: 27460768</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>boron ; Chemical compounds ; Chemical reactions ; Chemistry ; chromophores ; Conjugation ; cross-coupling ; donor-acceptor systems ; Emission ; Energy gaps (solid state) ; Energy of solution ; Fluid flow ; Fluorescence ; near-infrared fluorescence</subject><ispartof>Chemistry : a European journal, 2016-08, Vol.22 (35), p.12439-12448</ispartof><rights>2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6420-21413904030a170253356f4793ac72c936774a65124633055f071020790142cf3</citedby><cites>FETCH-LOGICAL-c6420-21413904030a170253356f4793ac72c936774a65124633055f071020790142cf3</cites><orcidid>0000-0001-9975-8302</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.201602010$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201602010$$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/27460768$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Crossley, Daniel L.</creatorcontrib><creatorcontrib>Vitorica-Yrezabal, Inigo</creatorcontrib><creatorcontrib>Humphries, Martin J.</creatorcontrib><creatorcontrib>Turner, Michael L.</creatorcontrib><creatorcontrib>Ingleson, Michael J.</creatorcontrib><title>Highly Emissive Far Red/Near-IR Fluorophores Based on Borylated Fluorene-Benzothiadiazole Donor-Acceptor Materials</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Stille, Suzuki–Miyaura and Negishi cross‐coupling reactions of bromine‐functionalised borylated precursors enable the facile, high yielding, synthesis of borylated donor–acceptor materials that contain electron‐rich aromatic units and/or extended effective conjugation lengths. These materials have large Stokes shifts, low LUMO energies, small band‐gaps and significant fluorescence emission >700 nm in solution and when dispersed in a host polymer.
The perfect couple: Cross‐coupling enables the high yielding synthesis of borylated donor–acceptor materials that contain electron‐rich aromatics units and/or extended effective conjugation lengths. These materials have large Stokes shifts, low LUMO energies, small band‐gaps and significant fluorescence emission >700 nm in solution and in the solid state.</description><subject>boron</subject><subject>Chemical compounds</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>chromophores</subject><subject>Conjugation</subject><subject>cross-coupling</subject><subject>donor-acceptor systems</subject><subject>Emission</subject><subject>Energy gaps (solid state)</subject><subject>Energy of solution</subject><subject>Fluid flow</subject><subject>Fluorescence</subject><subject>near-infrared fluorescence</subject><issn>0947-6539</issn><issn>1521-3765</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqNkc1vEzEQxS0EoqFw5YhW4sJl0_F3fEFq0qSp1ASpKuJoGcfbddmsg71bSP96nKZEhQtcPLLmN08z7yH0FsMQA5ATW7v1kAAWkB94hgaYE1xSKfhzNADFZCk4VUfoVUq3AKAEpS_REZFMgBSjAYpzf1M322K69in5O1fMTCyu3Opk6UwsL66KWdOHGDZ1iC4VY5PcqghtMQ5x25gufx76rnXl2LX3oau9WXlzHxpXnIU2xPLUWrfpQiwWGY_eNOk1elHl4t481mP0eTa9nszLy0_nF5PTy9IKRqAkmGGqgAEFgyUQTikXFZOKGiuJVVRIyYzgmLB8FHBegcTZBakAM2Ireow-7nU3_de1W1nXdtE0ehP92sStDsbrPzutr_VNuNNCjICMIAt8eBSI4XvvUqezSdY1jWld6JPGI8o5ZxxG_4FiTBTDbKf6_i_0NvSxzU48UIpwIXbUcE_ZGFKKrjrsjUHvkte75PUh-Tzw7um1B_x31BlQe-CHb9z2H3J6Mp8unoqX-1mfOvfzMGviNy0klVx_WZ7rswmopVzM9TX9Bafkxyk</recordid><startdate>20160822</startdate><enddate>20160822</enddate><creator>Crossley, Daniel L.</creator><creator>Vitorica-Yrezabal, Inigo</creator><creator>Humphries, Martin J.</creator><creator>Turner, Michael L.</creator><creator>Ingleson, Michael J.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>BSCLL</scope><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/0000-0001-9975-8302</orcidid></search><sort><creationdate>20160822</creationdate><title>Highly Emissive Far Red/Near-IR Fluorophores Based on Borylated Fluorene-Benzothiadiazole Donor-Acceptor Materials</title><author>Crossley, Daniel L. ; Vitorica-Yrezabal, Inigo ; Humphries, Martin J. ; Turner, Michael L. ; Ingleson, Michael J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6420-21413904030a170253356f4793ac72c936774a65124633055f071020790142cf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>boron</topic><topic>Chemical compounds</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>chromophores</topic><topic>Conjugation</topic><topic>cross-coupling</topic><topic>donor-acceptor systems</topic><topic>Emission</topic><topic>Energy gaps (solid state)</topic><topic>Energy of solution</topic><topic>Fluid flow</topic><topic>Fluorescence</topic><topic>near-infrared fluorescence</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Crossley, Daniel L.</creatorcontrib><creatorcontrib>Vitorica-Yrezabal, Inigo</creatorcontrib><creatorcontrib>Humphries, Martin J.</creatorcontrib><creatorcontrib>Turner, Michael L.</creatorcontrib><creatorcontrib>Ingleson, Michael J.</creatorcontrib><collection>Istex</collection><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>Crossley, Daniel L.</au><au>Vitorica-Yrezabal, Inigo</au><au>Humphries, Martin J.</au><au>Turner, Michael L.</au><au>Ingleson, Michael J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly Emissive Far Red/Near-IR Fluorophores Based on Borylated Fluorene-Benzothiadiazole Donor-Acceptor Materials</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2016-08-22</date><risdate>2016</risdate><volume>22</volume><issue>35</issue><spage>12439</spage><epage>12448</epage><pages>12439-12448</pages><issn>0947-6539</issn><issn>1521-3765</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Stille, Suzuki–Miyaura and Negishi cross‐coupling reactions of bromine‐functionalised borylated precursors enable the facile, high yielding, synthesis of borylated donor–acceptor materials that contain electron‐rich aromatic units and/or extended effective conjugation lengths. These materials have large Stokes shifts, low LUMO energies, small band‐gaps and significant fluorescence emission >700 nm in solution and when dispersed in a host polymer.
The perfect couple: Cross‐coupling enables the high yielding synthesis of borylated donor–acceptor materials that contain electron‐rich aromatics units and/or extended effective conjugation lengths. These materials have large Stokes shifts, low LUMO energies, small band‐gaps and significant fluorescence emission >700 nm in solution and in the solid state.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27460768</pmid><doi>10.1002/chem.201602010</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-9975-8302</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0947-6539 |
| ispartof | Chemistry : a European journal, 2016-08, Vol.22 (35), p.12439-12448 |
| issn | 0947-6539 1521-3765 1521-3765 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_6680280 |
| source | Access via Wiley Online Library |
| subjects | boron Chemical compounds Chemical reactions Chemistry chromophores Conjugation cross-coupling donor-acceptor systems Emission Energy gaps (solid state) Energy of solution Fluid flow Fluorescence near-infrared fluorescence |
| title | Highly Emissive Far Red/Near-IR Fluorophores Based on Borylated Fluorene-Benzothiadiazole Donor-Acceptor Materials |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-20T09%3A59%3A20IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Highly%20Emissive%20Far%20Red/Near-IR%20Fluorophores%20Based%20on%20Borylated%20Fluorene-Benzothiadiazole%20Donor-Acceptor%20Materials&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Crossley,%20Daniel%20L.&rft.date=2016-08-22&rft.volume=22&rft.issue=35&rft.spage=12439&rft.epage=12448&rft.pages=12439-12448&rft.issn=0947-6539&rft.eissn=1521-3765&rft.coden=CEUJED&rft_id=info:doi/10.1002/chem.201602010&rft_dat=%3Cproquest_pubme%3E1811294140%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1811925660&rft_id=info:pmid/27460768&rfr_iscdi=true |