Carbazole isomers induce ultralong organic phosphorescence
Commercial carbazole has been widely used to synthesize organic functional materials that have led to recent breakthroughs in ultralong organic phosphorescence 1 , thermally activated delayed fluorescence 2 , 3 , organic luminescent radicals 4 and organic semiconductor lasers 5 . However, the impact...
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| Veröffentlicht in: | Nature materials 2021-02, Vol.20 (2), p.175-180 |
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| creator | Chen, Chengjian Chi, Zhenguo Chong, Kok Chan Batsanov, Andrei S. Yang, Zhan Mao, Zhu Yang, Zhiyong Liu, Bin |
| description | Commercial carbazole has been widely used to synthesize organic functional materials that have led to recent breakthroughs in ultralong organic phosphorescence
1
, thermally activated delayed fluorescence
2
,
3
, organic luminescent radicals
4
and organic semiconductor lasers
5
. However, the impact of low-concentration isomeric impurities present within commercial batches on the properties of the synthesized molecules requires further analysis. Here, we have synthesized highly pure carbazole and observed that its fluorescence is blueshifted by 54 nm with respect to commercial samples and its room-temperature ultralong phosphorescence almost disappears
6
. We discover that such differences are due to the presence of a carbazole isomeric impurity in commercial carbazole sources, with concentrations |
| doi_str_mv | 10.1038/s41563-020-0797-2 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2444881240</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2444881240</sourcerecordid><originalsourceid>FETCH-LOGICAL-c518t-7ce18d4dc7db998c8e590836f1458f9126bacceb96c90a083ad7709c368a00df3</originalsourceid><addsrcrecordid>eNp1kE1LxDAQhoMorq7-AC9S8OKlOpOm-fAmi1-w4EXPIU3TtUu3WZPtQX-9WboqCB6GDMwzb4aHkDOEK4RCXkeGJS9yoJCDUCKne-QImeA54xz2dz0ipRNyHOMSgGJZ8kMyKagqpRTiiNzMTKjMp-9c1ka_ciFmbV8P1mVDtwmm8_0i82Fh-tZm6zcfUwUXreutOyEHjemiO929U_J6f_cye8znzw9Ps9t5bkuUm1xYh7JmtRV1pZS00pUKZMEbZKVsFFJeGWtdpbhVYNLE1EKAsgWXBqBuiim5HHPXwb8PLm70qk0XdJ3pnR-ipowxKZEySOjFH3Tph9Cn6xIlkSGFckvhSNngYwyu0evQrkz40Ah6K1aPYnUSq7diNU0757vkoVq5-mfj22QC6AjENOoXLvx-_X_qF1K_gpc</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2481412050</pqid></control><display><type>article</type><title>Carbazole isomers induce ultralong organic phosphorescence</title><source>MEDLINE</source><source>Nature</source><source>Alma/SFX Local Collection</source><creator>Chen, Chengjian ; Chi, Zhenguo ; Chong, Kok Chan ; Batsanov, Andrei S. ; Yang, Zhan ; Mao, Zhu ; Yang, Zhiyong ; Liu, Bin</creator><creatorcontrib>Chen, Chengjian ; Chi, Zhenguo ; Chong, Kok Chan ; Batsanov, Andrei S. ; Yang, Zhan ; Mao, Zhu ; Yang, Zhiyong ; Liu, Bin</creatorcontrib><description>Commercial carbazole has been widely used to synthesize organic functional materials that have led to recent breakthroughs in ultralong organic phosphorescence
1
, thermally activated delayed fluorescence
2
,
3
, organic luminescent radicals
4
and organic semiconductor lasers
5
. However, the impact of low-concentration isomeric impurities present within commercial batches on the properties of the synthesized molecules requires further analysis. Here, we have synthesized highly pure carbazole and observed that its fluorescence is blueshifted by 54 nm with respect to commercial samples and its room-temperature ultralong phosphorescence almost disappears
6
. We discover that such differences are due to the presence of a carbazole isomeric impurity in commercial carbazole sources, with concentrations <0.5 mol%. Ten representative carbazole derivatives synthesized from the highly pure carbazole failed to show the ultralong phosphorescence reported in the literature
1
,
7
–
15
. However, the phosphorescence was recovered by adding 0.1 mol% isomers, which act as charge traps. Investigating the role of the isomers may therefore provide alternative insights into the mechanisms behind ultralong organic phosphorescence
1
,
6
–
18
.
A carbazole isomer, typically present as an impurity in commercially produced carbazole batches, is shown to be responsible for the ultralong phosphorescence observed in these compounds and their derivatives.</description><identifier>ISSN: 1476-1122</identifier><identifier>EISSN: 1476-4660</identifier><identifier>DOI: 10.1038/s41563-020-0797-2</identifier><identifier>PMID: 32958877</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>140/131 ; 639/301/1019 ; 639/638/298 ; Biomaterials ; Carbazoles ; Carbazoles - chemical synthesis ; Carbazoles - chemistry ; Chemical synthesis ; Chemistry and Materials Science ; Chromatography ; Condensed Matter Physics ; Crystals ; Derivatives ; Fluorescence ; Functional materials ; Impurities ; Isomers ; Letter ; Materials Science ; Nanotechnology ; Optical and Electronic Materials ; Phosphorescence ; Room temperature ; Temperature</subject><ispartof>Nature materials, 2021-02, Vol.20 (2), p.175-180</ispartof><rights>The Author(s), under exclusive licence to Springer Nature Limited 2020</rights><rights>The Author(s), under exclusive licence to Springer Nature Limited 2020.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c518t-7ce18d4dc7db998c8e590836f1458f9126bacceb96c90a083ad7709c368a00df3</citedby><cites>FETCH-LOGICAL-c518t-7ce18d4dc7db998c8e590836f1458f9126bacceb96c90a083ad7709c368a00df3</cites><orcidid>0000-0003-2081-2252 ; 0000-0001-9772-5363 ; 0000-0002-0956-2777 ; 0000-0003-1670-9981</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27926,27927</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32958877$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Chengjian</creatorcontrib><creatorcontrib>Chi, Zhenguo</creatorcontrib><creatorcontrib>Chong, Kok Chan</creatorcontrib><creatorcontrib>Batsanov, Andrei S.</creatorcontrib><creatorcontrib>Yang, Zhan</creatorcontrib><creatorcontrib>Mao, Zhu</creatorcontrib><creatorcontrib>Yang, Zhiyong</creatorcontrib><creatorcontrib>Liu, Bin</creatorcontrib><title>Carbazole isomers induce ultralong organic phosphorescence</title><title>Nature materials</title><addtitle>Nat. Mater</addtitle><addtitle>Nat Mater</addtitle><description>Commercial carbazole has been widely used to synthesize organic functional materials that have led to recent breakthroughs in ultralong organic phosphorescence
1
, thermally activated delayed fluorescence
2
,
3
, organic luminescent radicals
4
and organic semiconductor lasers
5
. However, the impact of low-concentration isomeric impurities present within commercial batches on the properties of the synthesized molecules requires further analysis. Here, we have synthesized highly pure carbazole and observed that its fluorescence is blueshifted by 54 nm with respect to commercial samples and its room-temperature ultralong phosphorescence almost disappears
6
. We discover that such differences are due to the presence of a carbazole isomeric impurity in commercial carbazole sources, with concentrations <0.5 mol%. Ten representative carbazole derivatives synthesized from the highly pure carbazole failed to show the ultralong phosphorescence reported in the literature
1
,
7
–
15
. However, the phosphorescence was recovered by adding 0.1 mol% isomers, which act as charge traps. Investigating the role of the isomers may therefore provide alternative insights into the mechanisms behind ultralong organic phosphorescence
1
,
6
–
18
.
A carbazole isomer, typically present as an impurity in commercially produced carbazole batches, is shown to be responsible for the ultralong phosphorescence observed in these compounds and their derivatives.</description><subject>140/131</subject><subject>639/301/1019</subject><subject>639/638/298</subject><subject>Biomaterials</subject><subject>Carbazoles</subject><subject>Carbazoles - chemical synthesis</subject><subject>Carbazoles - chemistry</subject><subject>Chemical synthesis</subject><subject>Chemistry and Materials Science</subject><subject>Chromatography</subject><subject>Condensed Matter Physics</subject><subject>Crystals</subject><subject>Derivatives</subject><subject>Fluorescence</subject><subject>Functional materials</subject><subject>Impurities</subject><subject>Isomers</subject><subject>Letter</subject><subject>Materials Science</subject><subject>Nanotechnology</subject><subject>Optical and Electronic Materials</subject><subject>Phosphorescence</subject><subject>Room temperature</subject><subject>Temperature</subject><issn>1476-1122</issn><issn>1476-4660</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNp1kE1LxDAQhoMorq7-AC9S8OKlOpOm-fAmi1-w4EXPIU3TtUu3WZPtQX-9WboqCB6GDMwzb4aHkDOEK4RCXkeGJS9yoJCDUCKne-QImeA54xz2dz0ipRNyHOMSgGJZ8kMyKagqpRTiiNzMTKjMp-9c1ka_ciFmbV8P1mVDtwmm8_0i82Fh-tZm6zcfUwUXreutOyEHjemiO929U_J6f_cye8znzw9Ps9t5bkuUm1xYh7JmtRV1pZS00pUKZMEbZKVsFFJeGWtdpbhVYNLE1EKAsgWXBqBuiim5HHPXwb8PLm70qk0XdJ3pnR-ipowxKZEySOjFH3Tph9Cn6xIlkSGFckvhSNngYwyu0evQrkz40Ah6K1aPYnUSq7diNU0757vkoVq5-mfj22QC6AjENOoXLvx-_X_qF1K_gpc</recordid><startdate>20210201</startdate><enddate>20210201</enddate><creator>Chen, Chengjian</creator><creator>Chi, Zhenguo</creator><creator>Chong, Kok Chan</creator><creator>Batsanov, Andrei S.</creator><creator>Yang, Zhan</creator><creator>Mao, Zhu</creator><creator>Yang, Zhiyong</creator><creator>Liu, Bin</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7SR</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8AO</scope><scope>8BQ</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>K9.</scope><scope>KB.</scope><scope>L6V</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7S</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PTHSS</scope><scope>Q9U</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-2081-2252</orcidid><orcidid>https://orcid.org/0000-0001-9772-5363</orcidid><orcidid>https://orcid.org/0000-0002-0956-2777</orcidid><orcidid>https://orcid.org/0000-0003-1670-9981</orcidid></search><sort><creationdate>20210201</creationdate><title>Carbazole isomers induce ultralong organic phosphorescence</title><author>Chen, Chengjian ; Chi, Zhenguo ; Chong, Kok Chan ; Batsanov, Andrei S. ; Yang, Zhan ; Mao, Zhu ; Yang, Zhiyong ; Liu, Bin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c518t-7ce18d4dc7db998c8e590836f1458f9126bacceb96c90a083ad7709c368a00df3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>140/131</topic><topic>639/301/1019</topic><topic>639/638/298</topic><topic>Biomaterials</topic><topic>Carbazoles</topic><topic>Carbazoles - chemical synthesis</topic><topic>Carbazoles - chemistry</topic><topic>Chemical synthesis</topic><topic>Chemistry and Materials Science</topic><topic>Chromatography</topic><topic>Condensed Matter Physics</topic><topic>Crystals</topic><topic>Derivatives</topic><topic>Fluorescence</topic><topic>Functional materials</topic><topic>Impurities</topic><topic>Isomers</topic><topic>Letter</topic><topic>Materials Science</topic><topic>Nanotechnology</topic><topic>Optical and Electronic Materials</topic><topic>Phosphorescence</topic><topic>Room temperature</topic><topic>Temperature</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Chengjian</creatorcontrib><creatorcontrib>Chi, Zhenguo</creatorcontrib><creatorcontrib>Chong, Kok Chan</creatorcontrib><creatorcontrib>Batsanov, Andrei S.</creatorcontrib><creatorcontrib>Yang, Zhan</creatorcontrib><creatorcontrib>Mao, Zhu</creatorcontrib><creatorcontrib>Yang, Zhiyong</creatorcontrib><creatorcontrib>Liu, Bin</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Engineered Materials Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Materials Science Database</collection><collection>ProQuest Engineering Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Science Database</collection><collection>Engineering Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>Engineering Collection</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><jtitle>Nature materials</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Chengjian</au><au>Chi, Zhenguo</au><au>Chong, Kok Chan</au><au>Batsanov, Andrei S.</au><au>Yang, Zhan</au><au>Mao, Zhu</au><au>Yang, Zhiyong</au><au>Liu, Bin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Carbazole isomers induce ultralong organic phosphorescence</atitle><jtitle>Nature materials</jtitle><stitle>Nat. Mater</stitle><addtitle>Nat Mater</addtitle><date>2021-02-01</date><risdate>2021</risdate><volume>20</volume><issue>2</issue><spage>175</spage><epage>180</epage><pages>175-180</pages><issn>1476-1122</issn><eissn>1476-4660</eissn><abstract>Commercial carbazole has been widely used to synthesize organic functional materials that have led to recent breakthroughs in ultralong organic phosphorescence
1
, thermally activated delayed fluorescence
2
,
3
, organic luminescent radicals
4
and organic semiconductor lasers
5
. However, the impact of low-concentration isomeric impurities present within commercial batches on the properties of the synthesized molecules requires further analysis. Here, we have synthesized highly pure carbazole and observed that its fluorescence is blueshifted by 54 nm with respect to commercial samples and its room-temperature ultralong phosphorescence almost disappears
6
. We discover that such differences are due to the presence of a carbazole isomeric impurity in commercial carbazole sources, with concentrations <0.5 mol%. Ten representative carbazole derivatives synthesized from the highly pure carbazole failed to show the ultralong phosphorescence reported in the literature
1
,
7
–
15
. However, the phosphorescence was recovered by adding 0.1 mol% isomers, which act as charge traps. Investigating the role of the isomers may therefore provide alternative insights into the mechanisms behind ultralong organic phosphorescence
1
,
6
–
18
.
A carbazole isomer, typically present as an impurity in commercially produced carbazole batches, is shown to be responsible for the ultralong phosphorescence observed in these compounds and their derivatives.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>32958877</pmid><doi>10.1038/s41563-020-0797-2</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-2081-2252</orcidid><orcidid>https://orcid.org/0000-0001-9772-5363</orcidid><orcidid>https://orcid.org/0000-0002-0956-2777</orcidid><orcidid>https://orcid.org/0000-0003-1670-9981</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | 140/131 639/301/1019 639/638/298 Biomaterials Carbazoles Carbazoles - chemical synthesis Carbazoles - chemistry Chemical synthesis Chemistry and Materials Science Chromatography Condensed Matter Physics Crystals Derivatives Fluorescence Functional materials Impurities Isomers Letter Materials Science Nanotechnology Optical and Electronic Materials Phosphorescence Room temperature Temperature |
| title | Carbazole isomers induce ultralong organic phosphorescence |
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