Loading…
2,7‐Substituted N‐Carbazole Donors on Tris(2,4,6‐trichlorophenyl)methyl Radicals with High Quantum Yield
Doublet spin properties of organic open‐shell luminophores evade the formation of dark triplet states, thus making radicals favorable emitters for next generation organic light‐emitting diodes. However, their poor photostability and mediocre photoluminescence quantum yields (PLQYs) limit their appli...
Saved in:
Published in: | Advanced optical materials 2022-04, Vol.10 (7), p.n/a |
---|---|
Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
cited_by | cdi_FETCH-LOGICAL-c3571-985424f198e753447e55fd9c963cfbe56a29fea457835f0d83ed6fdee5625c393 |
---|---|
cites | cdi_FETCH-LOGICAL-c3571-985424f198e753447e55fd9c963cfbe56a29fea457835f0d83ed6fdee5625c393 |
container_end_page | n/a |
container_issue | 7 |
container_start_page | |
container_title | Advanced optical materials |
container_volume | 10 |
creator | Chen, Lisa Arnold, Mona Kittel, Yonca Blinder, Rémi Jelezko, Fedor Kuehne, Alexander J. C. |
description | Doublet spin properties of organic open‐shell luminophores evade the formation of dark triplet states, thus making radicals favorable emitters for next generation organic light‐emitting diodes. However, their poor photostability and mediocre photoluminescence quantum yields (PLQYs) limit their application. In this work, two series of trityl radicals functionalized with one, two, and three 2,7‐disubstituted carbazole units are presented. The authors either attach nitriles or bromines as electron‐withdrawing 2,7‐substituents. The resulting radical emitters exhibit outstanding optical properties. The electron‐withdrawing properties of the substituents lead to a blue‐shift of the emission, indicating a starting point for future emission engineering into the green spectrum. Due to the 2,7‐substitution of the carbazole moiety, the radical emitters are sterically more hindered than the commonly used 3,6‐substituted carbazoles. This steric hindrance reduces non‐radiative decay pathways in the molecules, enhancing photostability and pushing PLQYs up to 87%. Quantum mechanical calculations elucidate the influence of the electron withdrawing substituents on the optical performance of the open‐shell molecules. The authors also show that intensity borrowing from higher lying locally excited states contributes to these exceptionally high PLQYs.
Two series of trityl radicals functionalized with one to three 2,7‐disubstituted carbazole units are presented, carrying either nitriles or bromines as substituents. These electron‐withdrawing substituents in 2,7‐position induce a blue‐shift of emission and exceptional photoluminescence quantum yields up to 87%. Quantum mechanical calculations elucidate the electronic and steric properties of the molecules responsible for the outstanding optical performance. |
doi_str_mv | 10.1002/adom.202102101 |
format | article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2646725248</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2646725248</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3571-985424f198e753447e55fd9c963cfbe56a29fea457835f0d83ed6fdee5625c393</originalsourceid><addsrcrecordid>eNqFkM9Kw0AQxhdRsGivnhe8KDR1_ybZY2nVCtWi1oOnsE12zZYkW3cTSjz5CD6jT2JKRb0JAzMf8_tm4APgBKMhRohcyMyWQ4II3hbeAz2CBQ8wivD-n_kQ9L1fIYQ6QQWLeqAig-jz_eOxWfra1E2tMnjX6bF0S_lmCwUntrLOQ1vBhTP-jAzYIOyA2pk0L6yz61xVbXFeqjpvC_ggM5PKwsONqXM4NS85vG9kVTclfDaqyI7Bge7Wqv_dj8DT1eViPA1m8-ub8WgWpJRHOBAxZ4RpLGIVccpYpDjXmUhFSFO9VDyURGglGY9iyjXKYqqyUGeq2xCeUkGPwOnu7trZ10b5OlnZxlXdy4SELIwIJyzuqOGOSp313imdrJ0ppWsTjJJtrMk21uQn1s4gdoaNKVT7D52MJvPbX-8Xx9t94w</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2646725248</pqid></control><display><type>article</type><title>2,7‐Substituted N‐Carbazole Donors on Tris(2,4,6‐trichlorophenyl)methyl Radicals with High Quantum Yield</title><source>Wiley-Blackwell Read & Publish Collection</source><creator>Chen, Lisa ; Arnold, Mona ; Kittel, Yonca ; Blinder, Rémi ; Jelezko, Fedor ; Kuehne, Alexander J. C.</creator><creatorcontrib>Chen, Lisa ; Arnold, Mona ; Kittel, Yonca ; Blinder, Rémi ; Jelezko, Fedor ; Kuehne, Alexander J. C.</creatorcontrib><description>Doublet spin properties of organic open‐shell luminophores evade the formation of dark triplet states, thus making radicals favorable emitters for next generation organic light‐emitting diodes. However, their poor photostability and mediocre photoluminescence quantum yields (PLQYs) limit their application. In this work, two series of trityl radicals functionalized with one, two, and three 2,7‐disubstituted carbazole units are presented. The authors either attach nitriles or bromines as electron‐withdrawing 2,7‐substituents. The resulting radical emitters exhibit outstanding optical properties. The electron‐withdrawing properties of the substituents lead to a blue‐shift of the emission, indicating a starting point for future emission engineering into the green spectrum. Due to the 2,7‐substitution of the carbazole moiety, the radical emitters are sterically more hindered than the commonly used 3,6‐substituted carbazoles. This steric hindrance reduces non‐radiative decay pathways in the molecules, enhancing photostability and pushing PLQYs up to 87%. Quantum mechanical calculations elucidate the influence of the electron withdrawing substituents on the optical performance of the open‐shell molecules. The authors also show that intensity borrowing from higher lying locally excited states contributes to these exceptionally high PLQYs.
Two series of trityl radicals functionalized with one to three 2,7‐disubstituted carbazole units are presented, carrying either nitriles or bromines as substituents. These electron‐withdrawing substituents in 2,7‐position induce a blue‐shift of emission and exceptional photoluminescence quantum yields up to 87%. Quantum mechanical calculations elucidate the electronic and steric properties of the molecules responsible for the outstanding optical performance.</description><identifier>ISSN: 2195-1071</identifier><identifier>EISSN: 2195-1071</identifier><identifier>DOI: 10.1002/adom.202102101</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Bromine ; Carbazoles ; Electrons ; Emission ; Emitters ; Gomberg radicals ; Light emitting diodes ; Materials science ; Methyl radicals ; Nitriles ; open‐shell emitters ; Optical properties ; Optics ; Photoluminescence ; Quantum mechanics ; Steric hindrance ; Substitutes ; trityl radicals ; unpaired electrons</subject><ispartof>Advanced optical materials, 2022-04, Vol.10 (7), p.n/a</ispartof><rights>2022 The Authors. Advanced Optical Materials 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><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3571-985424f198e753447e55fd9c963cfbe56a29fea457835f0d83ed6fdee5625c393</citedby><cites>FETCH-LOGICAL-c3571-985424f198e753447e55fd9c963cfbe56a29fea457835f0d83ed6fdee5625c393</cites><orcidid>0000-0003-0142-8001</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Chen, Lisa</creatorcontrib><creatorcontrib>Arnold, Mona</creatorcontrib><creatorcontrib>Kittel, Yonca</creatorcontrib><creatorcontrib>Blinder, Rémi</creatorcontrib><creatorcontrib>Jelezko, Fedor</creatorcontrib><creatorcontrib>Kuehne, Alexander J. C.</creatorcontrib><title>2,7‐Substituted N‐Carbazole Donors on Tris(2,4,6‐trichlorophenyl)methyl Radicals with High Quantum Yield</title><title>Advanced optical materials</title><description>Doublet spin properties of organic open‐shell luminophores evade the formation of dark triplet states, thus making radicals favorable emitters for next generation organic light‐emitting diodes. However, their poor photostability and mediocre photoluminescence quantum yields (PLQYs) limit their application. In this work, two series of trityl radicals functionalized with one, two, and three 2,7‐disubstituted carbazole units are presented. The authors either attach nitriles or bromines as electron‐withdrawing 2,7‐substituents. The resulting radical emitters exhibit outstanding optical properties. The electron‐withdrawing properties of the substituents lead to a blue‐shift of the emission, indicating a starting point for future emission engineering into the green spectrum. Due to the 2,7‐substitution of the carbazole moiety, the radical emitters are sterically more hindered than the commonly used 3,6‐substituted carbazoles. This steric hindrance reduces non‐radiative decay pathways in the molecules, enhancing photostability and pushing PLQYs up to 87%. Quantum mechanical calculations elucidate the influence of the electron withdrawing substituents on the optical performance of the open‐shell molecules. The authors also show that intensity borrowing from higher lying locally excited states contributes to these exceptionally high PLQYs.
Two series of trityl radicals functionalized with one to three 2,7‐disubstituted carbazole units are presented, carrying either nitriles or bromines as substituents. These electron‐withdrawing substituents in 2,7‐position induce a blue‐shift of emission and exceptional photoluminescence quantum yields up to 87%. Quantum mechanical calculations elucidate the electronic and steric properties of the molecules responsible for the outstanding optical performance.</description><subject>Bromine</subject><subject>Carbazoles</subject><subject>Electrons</subject><subject>Emission</subject><subject>Emitters</subject><subject>Gomberg radicals</subject><subject>Light emitting diodes</subject><subject>Materials science</subject><subject>Methyl radicals</subject><subject>Nitriles</subject><subject>open‐shell emitters</subject><subject>Optical properties</subject><subject>Optics</subject><subject>Photoluminescence</subject><subject>Quantum mechanics</subject><subject>Steric hindrance</subject><subject>Substitutes</subject><subject>trityl radicals</subject><subject>unpaired electrons</subject><issn>2195-1071</issn><issn>2195-1071</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqFkM9Kw0AQxhdRsGivnhe8KDR1_ybZY2nVCtWi1oOnsE12zZYkW3cTSjz5CD6jT2JKRb0JAzMf8_tm4APgBKMhRohcyMyWQ4II3hbeAz2CBQ8wivD-n_kQ9L1fIYQ6QQWLeqAig-jz_eOxWfra1E2tMnjX6bF0S_lmCwUntrLOQ1vBhTP-jAzYIOyA2pk0L6yz61xVbXFeqjpvC_ggM5PKwsONqXM4NS85vG9kVTclfDaqyI7Bge7Wqv_dj8DT1eViPA1m8-ub8WgWpJRHOBAxZ4RpLGIVccpYpDjXmUhFSFO9VDyURGglGY9iyjXKYqqyUGeq2xCeUkGPwOnu7trZ10b5OlnZxlXdy4SELIwIJyzuqOGOSp313imdrJ0ppWsTjJJtrMk21uQn1s4gdoaNKVT7D52MJvPbX-8Xx9t94w</recordid><startdate>20220401</startdate><enddate>20220401</enddate><creator>Chen, Lisa</creator><creator>Arnold, Mona</creator><creator>Kittel, Yonca</creator><creator>Blinder, Rémi</creator><creator>Jelezko, Fedor</creator><creator>Kuehne, Alexander J. C.</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/0000-0003-0142-8001</orcidid></search><sort><creationdate>20220401</creationdate><title>2,7‐Substituted N‐Carbazole Donors on Tris(2,4,6‐trichlorophenyl)methyl Radicals with High Quantum Yield</title><author>Chen, Lisa ; Arnold, Mona ; Kittel, Yonca ; Blinder, Rémi ; Jelezko, Fedor ; Kuehne, Alexander J. C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3571-985424f198e753447e55fd9c963cfbe56a29fea457835f0d83ed6fdee5625c393</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Bromine</topic><topic>Carbazoles</topic><topic>Electrons</topic><topic>Emission</topic><topic>Emitters</topic><topic>Gomberg radicals</topic><topic>Light emitting diodes</topic><topic>Materials science</topic><topic>Methyl radicals</topic><topic>Nitriles</topic><topic>open‐shell emitters</topic><topic>Optical properties</topic><topic>Optics</topic><topic>Photoluminescence</topic><topic>Quantum mechanics</topic><topic>Steric hindrance</topic><topic>Substitutes</topic><topic>trityl radicals</topic><topic>unpaired electrons</topic><toplevel>online_resources</toplevel><creatorcontrib>Chen, Lisa</creatorcontrib><creatorcontrib>Arnold, Mona</creatorcontrib><creatorcontrib>Kittel, Yonca</creatorcontrib><creatorcontrib>Blinder, Rémi</creatorcontrib><creatorcontrib>Jelezko, Fedor</creatorcontrib><creatorcontrib>Kuehne, Alexander J. C.</creatorcontrib><collection>Wiley_OA刊</collection><collection>Wiley Online Library 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>Chen, Lisa</au><au>Arnold, Mona</au><au>Kittel, Yonca</au><au>Blinder, Rémi</au><au>Jelezko, Fedor</au><au>Kuehne, Alexander J. C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>2,7‐Substituted N‐Carbazole Donors on Tris(2,4,6‐trichlorophenyl)methyl Radicals with High Quantum Yield</atitle><jtitle>Advanced optical materials</jtitle><date>2022-04-01</date><risdate>2022</risdate><volume>10</volume><issue>7</issue><epage>n/a</epage><issn>2195-1071</issn><eissn>2195-1071</eissn><abstract>Doublet spin properties of organic open‐shell luminophores evade the formation of dark triplet states, thus making radicals favorable emitters for next generation organic light‐emitting diodes. However, their poor photostability and mediocre photoluminescence quantum yields (PLQYs) limit their application. In this work, two series of trityl radicals functionalized with one, two, and three 2,7‐disubstituted carbazole units are presented. The authors either attach nitriles or bromines as electron‐withdrawing 2,7‐substituents. The resulting radical emitters exhibit outstanding optical properties. The electron‐withdrawing properties of the substituents lead to a blue‐shift of the emission, indicating a starting point for future emission engineering into the green spectrum. Due to the 2,7‐substitution of the carbazole moiety, the radical emitters are sterically more hindered than the commonly used 3,6‐substituted carbazoles. This steric hindrance reduces non‐radiative decay pathways in the molecules, enhancing photostability and pushing PLQYs up to 87%. Quantum mechanical calculations elucidate the influence of the electron withdrawing substituents on the optical performance of the open‐shell molecules. The authors also show that intensity borrowing from higher lying locally excited states contributes to these exceptionally high PLQYs.
Two series of trityl radicals functionalized with one to three 2,7‐disubstituted carbazole units are presented, carrying either nitriles or bromines as substituents. These electron‐withdrawing substituents in 2,7‐position induce a blue‐shift of emission and exceptional photoluminescence quantum yields up to 87%. Quantum mechanical calculations elucidate the electronic and steric properties of the molecules responsible for the outstanding optical performance.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adom.202102101</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-0142-8001</orcidid><oa>free_for_read</oa></addata></record> |
fulltext | fulltext |
identifier | ISSN: 2195-1071 |
ispartof | Advanced optical materials, 2022-04, Vol.10 (7), p.n/a |
issn | 2195-1071 2195-1071 |
language | eng |
recordid | cdi_proquest_journals_2646725248 |
source | Wiley-Blackwell Read & Publish Collection |
subjects | Bromine Carbazoles Electrons Emission Emitters Gomberg radicals Light emitting diodes Materials science Methyl radicals Nitriles open‐shell emitters Optical properties Optics Photoluminescence Quantum mechanics Steric hindrance Substitutes trityl radicals unpaired electrons |
title | 2,7‐Substituted N‐Carbazole Donors on Tris(2,4,6‐trichlorophenyl)methyl Radicals with High Quantum Yield |
url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-03T08%3A39%3A25IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=2,7%E2%80%90Substituted%20N%E2%80%90Carbazole%20Donors%20on%20Tris(2,4,6%E2%80%90trichlorophenyl)methyl%20Radicals%20with%20High%20Quantum%20Yield&rft.jtitle=Advanced%20optical%20materials&rft.au=Chen,%20Lisa&rft.date=2022-04-01&rft.volume=10&rft.issue=7&rft.epage=n/a&rft.issn=2195-1071&rft.eissn=2195-1071&rft_id=info:doi/10.1002/adom.202102101&rft_dat=%3Cproquest_cross%3E2646725248%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c3571-985424f198e753447e55fd9c963cfbe56a29fea457835f0d83ed6fdee5625c393%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2646725248&rft_id=info:pmid/&rfr_iscdi=true |