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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| Published in | Nature materials Vol. 20; no. 2; pp. 175 - 180 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
London
Nature Publishing Group UK
01.02.2021
Nature Publishing Group |
| Subjects | |
| Online Access | Get full text |
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| 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. |
|---|---|
| AbstractList | 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. Commercial carbazole has been widely used to synthesize organic functional materials that have led to recent breakthroughs in ultralong organic phosphorescence1, thermally activated delayed fluorescence2,3, organic luminescent radicals4 and organic semiconductor lasers5. 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 disappears6. 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 literature1,7–15. 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 phosphorescence1,6–18.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. Commercial carbazole has been widely used to synthesize organic functional materials that have led to recent breakthroughs in ultralong organic phosphorescence , thermally activated delayed fluorescence , organic luminescent radicals and organic semiconductor lasers . 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 . 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 . 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 . Commercial carbazole has been widely used to synthesize organic functional materials that have led to recent breakthroughs in ultralong organic phosphorescence1, thermally activated delayed fluorescence2,3, organic luminescent radicals4 and organic semiconductor lasers5. 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 disappears6. 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 literature1,7-15. 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 phosphorescence1,6-18.Commercial carbazole has been widely used to synthesize organic functional materials that have led to recent breakthroughs in ultralong organic phosphorescence1, thermally activated delayed fluorescence2,3, organic luminescent radicals4 and organic semiconductor lasers5. 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 disappears6. 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 literature1,7-15. 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 phosphorescence1,6-18. |
| Author | Chong, Kok Chan Liu, Bin Mao, Zhu Yang, Zhiyong Chen, Chengjian Chi, Zhenguo Batsanov, Andrei S. Yang, Zhan |
| Author_xml | – sequence: 1 givenname: Chengjian orcidid: 0000-0003-2081-2252 surname: Chen fullname: Chen, Chengjian organization: Department of Chemical and Biomolecular Engineering, National University of Singapore – sequence: 2 givenname: Zhenguo orcidid: 0000-0001-9772-5363 surname: Chi fullname: Chi, Zhenguo organization: School of Chemistry, Sun Yat-sen University – sequence: 3 givenname: Kok Chan surname: Chong fullname: Chong, Kok Chan organization: Department of Chemical and Biomolecular Engineering, National University of Singapore – sequence: 4 givenname: Andrei S. surname: Batsanov fullname: Batsanov, Andrei S. organization: Department of Chemistry, Durham University – sequence: 5 givenname: Zhan surname: Yang fullname: Yang, Zhan organization: School of Chemistry, Sun Yat-sen University – sequence: 6 givenname: Zhu surname: Mao fullname: Mao, Zhu organization: School of Chemistry, Sun Yat-sen University – sequence: 7 givenname: Zhiyong orcidid: 0000-0003-1670-9981 surname: Yang fullname: Yang, Zhiyong organization: School of Chemistry, Sun Yat-sen University – sequence: 8 givenname: Bin orcidid: 0000-0002-0956-2777 surname: Liu fullname: Liu, Bin email: cheliub@nus.edu.sg organization: Department of Chemical and Biomolecular Engineering, National University of Singapore, Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32958877$$D View this record in MEDLINE/PubMed |
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| Snippet | Commercial carbazole has been widely used to synthesize organic functional materials that have led to recent breakthroughs in ultralong organic phosphorescence... Commercial carbazole has been widely used to synthesize organic functional materials that have led to recent breakthroughs in ultralong organic... |
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| SubjectTerms | 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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