Anthraquinone-based intramolecular charge-transfer compounds: computational molecular design, thermally activated delayed fluorescence, and highly efficient red electroluminescence.
Identifieur interne : 000C75 ( Ncbi/Curation ); précédent : 000C74; suivant : 000C76Anthraquinone-based intramolecular charge-transfer compounds: computational molecular design, thermally activated delayed fluorescence, and highly efficient red electroluminescence.
Auteurs : Qisheng Zhang [Japon] ; Hirokazu Kuwabara ; William J. Potscavage ; Shuping Huang ; Yasuhiro Hatae ; Takumi Shibata ; Chihaya AdachiSource :
- Journal of the American Chemical Society ; 2014.
Abstract
Red fluorescent molecules suffer from large, non-radiative internal conversion rates (k(IC)) governed by the energy gap law. To design efficient red thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs), a large fluorescence rate (k(F)) as well as a small energy difference between the lowest singlet and triplet excited states (ΔE(ST)) is necessary. Herein, we demonstrated that increasing the distance between donor (D) and acceptor (A) in intramolecular-charge-transfer molecules is a promising strategy for simultaneously achieving small ΔE(ST) and large k(F). Four D-Ph-A-Ph-D-type molecules with an anthraquinone acceptor, phenyl (Ph) bridge, and various donors were designed, synthesized, and compared with corresponding D-A-D-type molecules. Yellow to red TADF was observed from all of them. The k(F) and ΔE(ST) values determined from the measurements of quantum yield and lifetime of the fluorescence and TADF components are in good agreement with those predicted by corrected time-dependent density functional theory and are approximatively proportional to the square of the cosine of the theoretical twisting angles between each subunit. However, the introduction of a Ph-bridge was found to enhance k(F) without increasing ΔE(ST). Molecular simulation revealed a twisting and stretching motion of the N-C bond in the D-A-type molecules, which is thought to lower ΔE(ST) and k(F) but raise k(IC), that was experimentally confirmed in both solution and doped film. OLEDs containing D-Ph-A-Ph-D-type molecules with diphenylamine and bis(4-biphenyl)amine donors demonstrated maximum external quantum efficiencies of 12.5% and 9.0% with emission peaks at 624 and 637 nm, respectively.
DOI: 10.1021/ja510144h
PubMed: 25469624
Links toward previous steps (curation, corpus...)
- to stream PubMed, to step Corpus: Pour aller vers cette notice dans l'étape Curation :000128
- to stream PubMed, to step Curation: Pour aller vers cette notice dans l'étape Curation :000128
- to stream PubMed, to step Checkpoint: Pour aller vers cette notice dans l'étape Curation :000188
- to stream Ncbi, to step Merge: Pour aller vers cette notice dans l'étape Curation :000C75
Links to Exploration step
pubmed:25469624Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Anthraquinone-based intramolecular charge-transfer compounds: computational molecular design, thermally activated delayed fluorescence, and highly efficient red electroluminescence.</title><author><name sortKey="Zhang, Qisheng" sort="Zhang, Qisheng" uniqKey="Zhang Q" first="Qisheng" last="Zhang">Qisheng Zhang</name><affiliation wicri:level="1"><nlm:affiliation>Center for Organic Photonics and Electronics Research (OPERA), Kyushu University , 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Center for Organic Photonics and Electronics Research (OPERA), Kyushu University , 744 Motooka, Nishi-ku, Fukuoka 819-0395</wicri:regionArea><wicri:noRegion>Fukuoka 819-0395</wicri:noRegion></affiliation></author><author><name sortKey="Kuwabara, Hirokazu" sort="Kuwabara, Hirokazu" uniqKey="Kuwabara H" first="Hirokazu" last="Kuwabara">Hirokazu Kuwabara</name></author><author><name sortKey="Potscavage, William J" sort="Potscavage, William J" uniqKey="Potscavage W" first="William J" last="Potscavage">William J. Potscavage</name></author><author><name sortKey="Huang, Shuping" sort="Huang, Shuping" uniqKey="Huang S" first="Shuping" last="Huang">Shuping Huang</name></author><author><name sortKey="Hatae, Yasuhiro" sort="Hatae, Yasuhiro" uniqKey="Hatae Y" first="Yasuhiro" last="Hatae">Yasuhiro Hatae</name></author><author><name sortKey="Shibata, Takumi" sort="Shibata, Takumi" uniqKey="Shibata T" first="Takumi" last="Shibata">Takumi Shibata</name></author><author><name sortKey="Adachi, Chihaya" sort="Adachi, Chihaya" uniqKey="Adachi C" first="Chihaya" last="Adachi">Chihaya Adachi</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2014">2014</date><idno type="doi">10.1021/ja510144h</idno><idno type="RBID">pubmed:25469624</idno><idno type="pmid">25469624</idno><idno type="wicri:Area/PubMed/Corpus">000128</idno><idno type="wicri:Area/PubMed/Curation">000128</idno><idno type="wicri:Area/PubMed/Checkpoint">000188</idno><idno type="wicri:Area/Ncbi/Merge">000C75</idno><idno type="wicri:Area/Ncbi/Curation">000C75</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Anthraquinone-based intramolecular charge-transfer compounds: computational molecular design, thermally activated delayed fluorescence, and highly efficient red electroluminescence.</title><author><name sortKey="Zhang, Qisheng" sort="Zhang, Qisheng" uniqKey="Zhang Q" first="Qisheng" last="Zhang">Qisheng Zhang</name><affiliation wicri:level="1"><nlm:affiliation>Center for Organic Photonics and Electronics Research (OPERA), Kyushu University , 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Center for Organic Photonics and Electronics Research (OPERA), Kyushu University , 744 Motooka, Nishi-ku, Fukuoka 819-0395</wicri:regionArea><wicri:noRegion>Fukuoka 819-0395</wicri:noRegion></affiliation></author><author><name sortKey="Kuwabara, Hirokazu" sort="Kuwabara, Hirokazu" uniqKey="Kuwabara H" first="Hirokazu" last="Kuwabara">Hirokazu Kuwabara</name></author><author><name sortKey="Potscavage, William J" sort="Potscavage, William J" uniqKey="Potscavage W" first="William J" last="Potscavage">William J. Potscavage</name></author><author><name sortKey="Huang, Shuping" sort="Huang, Shuping" uniqKey="Huang S" first="Shuping" last="Huang">Shuping Huang</name></author><author><name sortKey="Hatae, Yasuhiro" sort="Hatae, Yasuhiro" uniqKey="Hatae Y" first="Yasuhiro" last="Hatae">Yasuhiro Hatae</name></author><author><name sortKey="Shibata, Takumi" sort="Shibata, Takumi" uniqKey="Shibata T" first="Takumi" last="Shibata">Takumi Shibata</name></author><author><name sortKey="Adachi, Chihaya" sort="Adachi, Chihaya" uniqKey="Adachi C" first="Chihaya" last="Adachi">Chihaya Adachi</name></author></analytic><series><title level="j">Journal of the American Chemical Society</title><idno type="e-ISSN">1520-5126</idno><imprint><date when="2014" type="published">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Red fluorescent molecules suffer from large, non-radiative internal conversion rates (k(IC)) governed by the energy gap law. To design efficient red thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs), a large fluorescence rate (k(F)) as well as a small energy difference between the lowest singlet and triplet excited states (ΔE(ST)) is necessary. Herein, we demonstrated that increasing the distance between donor (D) and acceptor (A) in intramolecular-charge-transfer molecules is a promising strategy for simultaneously achieving small ΔE(ST) and large k(F). Four D-Ph-A-Ph-D-type molecules with an anthraquinone acceptor, phenyl (Ph) bridge, and various donors were designed, synthesized, and compared with corresponding D-A-D-type molecules. Yellow to red TADF was observed from all of them. The k(F) and ΔE(ST) values determined from the measurements of quantum yield and lifetime of the fluorescence and TADF components are in good agreement with those predicted by corrected time-dependent density functional theory and are approximatively proportional to the square of the cosine of the theoretical twisting angles between each subunit. However, the introduction of a Ph-bridge was found to enhance k(F) without increasing ΔE(ST). Molecular simulation revealed a twisting and stretching motion of the N-C bond in the D-A-type molecules, which is thought to lower ΔE(ST) and k(F) but raise k(IC), that was experimentally confirmed in both solution and doped film. OLEDs containing D-Ph-A-Ph-D-type molecules with diphenylamine and bis(4-biphenyl)amine donors demonstrated maximum external quantum efficiencies of 12.5% and 9.0% with emission peaks at 624 and 637 nm, respectively.</div></front></TEI></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/Musique/explor/OperaV1/Data/Ncbi/Curation
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000C75 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Ncbi/Curation/biblio.hfd -nk 000C75 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Wicri/Musique
|area= OperaV1
|flux= Ncbi
|étape= Curation
|type= RBID
|clé= pubmed:25469624
|texte= Anthraquinone-based intramolecular charge-transfer compounds: computational molecular design, thermally activated delayed fluorescence, and highly efficient red electroluminescence.
}}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/Ncbi/Curation/RBID.i -Sk "pubmed:25469624" \
| HfdSelect -Kh $EXPLOR_AREA/Data/Ncbi/Curation/biblio.hfd \
| NlmPubMed2Wicri -a OperaV1
| This area was generated with Dilib version V0.6.21. |  |