An Unexpected Boron Rearrangement Leads to a Fluorogenic and Colorimetric BODIPY Probe
The isolation and characterization of a kinetically stable oxadiazaborinine (ODB) dye are described, which undergoes an unexpected thermal boron rearrangement with a color change and increase in fluorescence. This controllable reaction allows for the use as a practical time‐temperature indicator pro...
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| Veröffentlicht in: | Advanced optical materials 2023-03, Vol.11 (6), p.n/a |
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| container_title | Advanced optical materials |
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| creator | Merkes, Jean Michel Raabe, Gerhard Kiessling, Fabian Rueping, Magnus Banala, Srinivas |
| description | The isolation and characterization of a kinetically stable oxadiazaborinine (ODB) dye are described, which undergoes an unexpected thermal boron rearrangement with a color change and increase in fluorescence. This controllable reaction allows for the use as a practical time‐temperature indicator probe with the advantages of photostability, non‐reversibility, and environmental friendliness.
The novel oxadiazaborinin dye described here undergoes a temperature and solvent‐dependent, irreversible O‐ to N‐ rearrangement of the BF2 group or a cleavage of BF2 and acetyl groups, accompanied by a change in color and fluorescence. These changes can be used to quantify the integrated temperature fluctuations of cold‐chain logistics of perishable products. |
| doi_str_mv | 10.1002/adom.202202601 |
| format | Article |
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The novel oxadiazaborinin dye described here undergoes a temperature and solvent‐dependent, irreversible O‐ to N‐ rearrangement of the BF2 group or a cleavage of BF2 and acetyl groups, accompanied by a change in color and fluorescence. These changes can be used to quantify the integrated temperature fluctuations of cold‐chain logistics of perishable products.</description><identifier>ISSN: 2195-1071</identifier><identifier>EISSN: 2195-1071</identifier><identifier>DOI: 10.1002/adom.202202601</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Boron ; boron rearrangement ; Controllability ; dyes/pigments ; fluorescent probes ; Materials science ; Optics ; time‐temperature indicators</subject><ispartof>Advanced optical materials, 2023-03, Vol.11 (6), p.n/a</ispartof><rights>2023 The Authors. Advanced Optical Materials published by Wiley‐VCH GmbH</rights><rights>2023. 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><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3571-1b6a7e90a5532b45b8a0fcecbb7601af10f729c214f19c51e28847853459107c3</citedby><cites>FETCH-LOGICAL-c3571-1b6a7e90a5532b45b8a0fcecbb7601af10f729c214f19c51e28847853459107c3</cites><orcidid>0000-0003-3562-377X ; 0000-0002-7341-0399 ; 0000-0002-3964-9320 ; 0000-0003-4580-5227</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%2Fadom.202202601$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadom.202202601$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids></links><search><creatorcontrib>Merkes, Jean Michel</creatorcontrib><creatorcontrib>Raabe, Gerhard</creatorcontrib><creatorcontrib>Kiessling, Fabian</creatorcontrib><creatorcontrib>Rueping, Magnus</creatorcontrib><creatorcontrib>Banala, Srinivas</creatorcontrib><title>An Unexpected Boron Rearrangement Leads to a Fluorogenic and Colorimetric BODIPY Probe</title><title>Advanced optical materials</title><description>The isolation and characterization of a kinetically stable oxadiazaborinine (ODB) dye are described, which undergoes an unexpected thermal boron rearrangement with a color change and increase in fluorescence. This controllable reaction allows for the use as a practical time‐temperature indicator probe with the advantages of photostability, non‐reversibility, and environmental friendliness.
The novel oxadiazaborinin dye described here undergoes a temperature and solvent‐dependent, irreversible O‐ to N‐ rearrangement of the BF2 group or a cleavage of BF2 and acetyl groups, accompanied by a change in color and fluorescence. These changes can be used to quantify the integrated temperature fluctuations of cold‐chain logistics of perishable products.</description><subject>Boron</subject><subject>boron rearrangement</subject><subject>Controllability</subject><subject>dyes/pigments</subject><subject>fluorescent probes</subject><subject>Materials science</subject><subject>Optics</subject><subject>time‐temperature indicators</subject><issn>2195-1071</issn><issn>2195-1071</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFUE1LAzEQDaJgqb16Dnjemslumt1jP_woVFrECp5CNjtbWrZJTbZo_70pFfUmDMwH783Me4RcA-sDY_xWV27b54zHGDA4Ix0OhUiASTj_U1-SXggbxlhs0iKTHfI6tHRp8XOHpsWKjpx3lj6j9l7bFW7RtnSGugq0dVTT-2YfASu0a0O1rejYNc6vt9j6OBjNJ9PFG114V-IVuah1E7D3nbtkeX_3Mn5MZvOH6Xg4S0wqJCRQDrTEgmkhUl5mosw1qw2aspRRha6B1ZIXhkNWQ2EEIM_zTOYizUQRJZi0S25Oe3feve8xtGrj9t7Gk4rLXAoQHAYR1T-hjHcheKzVLn6t_UEBU0f71NE-9WNfJBQnwse6wcM_aDWczJ9-uV_ROHG1</recordid><startdate>20230301</startdate><enddate>20230301</enddate><creator>Merkes, Jean Michel</creator><creator>Raabe, Gerhard</creator><creator>Kiessling, Fabian</creator><creator>Rueping, Magnus</creator><creator>Banala, Srinivas</creator><general>Wiley Subscription Services, Inc</general><scope>24P</scope><scope>WIN</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SP</scope><scope>7U5</scope><scope>8FD</scope><scope>H8D</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0003-3562-377X</orcidid><orcidid>https://orcid.org/0000-0002-7341-0399</orcidid><orcidid>https://orcid.org/0000-0002-3964-9320</orcidid><orcidid>https://orcid.org/0000-0003-4580-5227</orcidid></search><sort><creationdate>20230301</creationdate><title>An Unexpected Boron Rearrangement Leads to a Fluorogenic and Colorimetric BODIPY Probe</title><author>Merkes, Jean Michel ; Raabe, Gerhard ; Kiessling, Fabian ; Rueping, Magnus ; Banala, Srinivas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3571-1b6a7e90a5532b45b8a0fcecbb7601af10f729c214f19c51e28847853459107c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Boron</topic><topic>boron rearrangement</topic><topic>Controllability</topic><topic>dyes/pigments</topic><topic>fluorescent probes</topic><topic>Materials science</topic><topic>Optics</topic><topic>time‐temperature indicators</topic><toplevel>online_resources</toplevel><creatorcontrib>Merkes, Jean Michel</creatorcontrib><creatorcontrib>Raabe, Gerhard</creatorcontrib><creatorcontrib>Kiessling, Fabian</creatorcontrib><creatorcontrib>Rueping, Magnus</creatorcontrib><creatorcontrib>Banala, Srinivas</creatorcontrib><collection>Wiley-Blackwell Open Access Titles</collection><collection>Wiley Free Content</collection><collection>CrossRef</collection><collection>Electronics & Communications Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Aerospace Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced optical materials</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Merkes, Jean Michel</au><au>Raabe, Gerhard</au><au>Kiessling, Fabian</au><au>Rueping, Magnus</au><au>Banala, Srinivas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Unexpected Boron Rearrangement Leads to a Fluorogenic and Colorimetric BODIPY Probe</atitle><jtitle>Advanced optical materials</jtitle><date>2023-03-01</date><risdate>2023</risdate><volume>11</volume><issue>6</issue><epage>n/a</epage><issn>2195-1071</issn><eissn>2195-1071</eissn><abstract>The isolation and characterization of a kinetically stable oxadiazaborinine (ODB) dye are described, which undergoes an unexpected thermal boron rearrangement with a color change and increase in fluorescence. This controllable reaction allows for the use as a practical time‐temperature indicator probe with the advantages of photostability, non‐reversibility, and environmental friendliness.
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| subjects | Boron boron rearrangement Controllability dyes/pigments fluorescent probes Materials science Optics time‐temperature indicators |
| title | An Unexpected Boron Rearrangement Leads to a Fluorogenic and Colorimetric BODIPY Probe |
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