High Performance Near-Infrared Emitters with Methylated Triphenylamine and Thiadiazolo[3,4-g]quinoxaline-Based Fluorophores

Three near-infrared emitters (2TPA-QBT, 2MeTPA-BT and TPA-QBT-MeTPA) were rationally designed and synthesized. Density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations showed that the introduction of mo...

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Autores principales:	Youming Zhang, Chengjun Wu, Minrong Zhu, Jingsheng Miao
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	near-infrared emitters hybridized local and charge transfer organic light-emitting diodes electroluminescence Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/9cc4b65cba7b45a0982613df7e3ffe47
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spelling	oai:doaj.org-article:9cc4b65cba7b45a0982613df7e3ffe472021-11-11T18:24:45ZHigh Performance Near-Infrared Emitters with Methylated Triphenylamine and Thiadiazolo[3,4-g]quinoxaline-Based Fluorophores10.3390/molecules262163861420-3049https://doaj.org/article/9cc4b65cba7b45a0982613df7e3ffe472021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6386https://doaj.org/toc/1420-3049Three near-infrared emitters (<b>2TPA-QBT</b>, <b>2MeTPA-BT</b> and <b>TPA-QBT-MeTPA</b>) were rationally designed and synthesized. Density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations showed that the introduction of mono- or di-methyl groups between the donors and acceptor could result in the spatial configuration changing greatly for <b>2MeTPA-QBT</b> and <b>TPA-QBT-MeTPA</b> compared to their parent compound <b>2TPA-QBT</b>. The emission of <b>TPA-QBT-MeTPA</b> had a more obvious hybridized local and charge transfer feature (HLCT) based on the influence of the steric hindrance of the methyl substituent. Attributed to their different spatial configurations and luminescence mechanisms, different emission wavelengths with photoluminescent quantum yields of 26%, 38% and 34% in toluene, as well as 24%, 27% and 31% in 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP) doped film, were observed for <b>2TPA-QBT</b>, <b>2MeTPA-QBT</b> and <b>TPA-QBT-MeTPA</b>, respectively. The constructed organic light-emitting devices (OLEDs) displayed electroluminescence with emission peaks at 728, 693 and 710 nm, with maximum external quantum efficiencies of 1.58%, 1.33% and 3.02% for the <b>2TPA-QBT</b>, <b>2MeTPA-QBT</b> and <b>TPA-QBT-MeTPA</b>-doped OLEDs, respectively. This work illustrated the effect of spatial configuration changes on the luminescence properties of donor-acceptor-type organic emitters.Youming ZhangChengjun WuMinrong ZhuJingsheng MiaoMDPI AGarticlenear-infrared emittershybridized local and charge transferorganic light-emitting diodeselectroluminescenceOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6386, p 6386 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	near-infrared emitters hybridized local and charge transfer organic light-emitting diodes electroluminescence Organic chemistry QD241-441
spellingShingle	near-infrared emitters hybridized local and charge transfer organic light-emitting diodes electroluminescence Organic chemistry QD241-441 Youming Zhang Chengjun Wu Minrong Zhu Jingsheng Miao High Performance Near-Infrared Emitters with Methylated Triphenylamine and Thiadiazolo[3,4-g]quinoxaline-Based Fluorophores
description	Three near-infrared emitters (<b>2TPA-QBT</b>, <b>2MeTPA-BT</b> and <b>TPA-QBT-MeTPA</b>) were rationally designed and synthesized. Density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations showed that the introduction of mono- or di-methyl groups between the donors and acceptor could result in the spatial configuration changing greatly for <b>2MeTPA-QBT</b> and <b>TPA-QBT-MeTPA</b> compared to their parent compound <b>2TPA-QBT</b>. The emission of <b>TPA-QBT-MeTPA</b> had a more obvious hybridized local and charge transfer feature (HLCT) based on the influence of the steric hindrance of the methyl substituent. Attributed to their different spatial configurations and luminescence mechanisms, different emission wavelengths with photoluminescent quantum yields of 26%, 38% and 34% in toluene, as well as 24%, 27% and 31% in 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP) doped film, were observed for <b>2TPA-QBT</b>, <b>2MeTPA-QBT</b> and <b>TPA-QBT-MeTPA</b>, respectively. The constructed organic light-emitting devices (OLEDs) displayed electroluminescence with emission peaks at 728, 693 and 710 nm, with maximum external quantum efficiencies of 1.58%, 1.33% and 3.02% for the <b>2TPA-QBT</b>, <b>2MeTPA-QBT</b> and <b>TPA-QBT-MeTPA</b>-doped OLEDs, respectively. This work illustrated the effect of spatial configuration changes on the luminescence properties of donor-acceptor-type organic emitters.
format	article
author	Youming Zhang Chengjun Wu Minrong Zhu Jingsheng Miao
author_facet	Youming Zhang Chengjun Wu Minrong Zhu Jingsheng Miao
author_sort	Youming Zhang
title	High Performance Near-Infrared Emitters with Methylated Triphenylamine and Thiadiazolo[3,4-g]quinoxaline-Based Fluorophores
title_short	High Performance Near-Infrared Emitters with Methylated Triphenylamine and Thiadiazolo[3,4-g]quinoxaline-Based Fluorophores
title_full	High Performance Near-Infrared Emitters with Methylated Triphenylamine and Thiadiazolo[3,4-g]quinoxaline-Based Fluorophores
title_fullStr	High Performance Near-Infrared Emitters with Methylated Triphenylamine and Thiadiazolo[3,4-g]quinoxaline-Based Fluorophores
title_full_unstemmed	High Performance Near-Infrared Emitters with Methylated Triphenylamine and Thiadiazolo[3,4-g]quinoxaline-Based Fluorophores
title_sort	high performance near-infrared emitters with methylated triphenylamine and thiadiazolo[3,4-g]quinoxaline-based fluorophores
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/9cc4b65cba7b45a0982613df7e3ffe47
work_keys_str_mv	AT youmingzhang highperformancenearinfraredemitterswithmethylatedtriphenylamineandthiadiazolo34gquinoxalinebasedfluorophores AT chengjunwu highperformancenearinfraredemitterswithmethylatedtriphenylamineandthiadiazolo34gquinoxalinebasedfluorophores AT minrongzhu highperformancenearinfraredemitterswithmethylatedtriphenylamineandthiadiazolo34gquinoxalinebasedfluorophores AT jingshengmiao highperformancenearinfraredemitterswithmethylatedtriphenylamineandthiadiazolo34gquinoxalinebasedfluorophores
_version_	1718431839722405888

High Performance Near-Infrared Emitters with Methylated Triphenylamine and Thiadiazolo[3,4-g]quinoxaline-Based Fluorophores

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