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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 mono- or di-methyl groups between the donors and acceptor c...

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Autores principales: Zhang, Youming, Wu, Chengjun, Zhu, Minrong, Miao, Jingsheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8588353/
https://www.ncbi.nlm.nih.gov/pubmed/34770795
http://dx.doi.org/10.3390/molecules26216386
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author Zhang, Youming
Wu, Chengjun
Zhu, Minrong
Miao, Jingsheng
author_facet Zhang, Youming
Wu, Chengjun
Zhu, Minrong
Miao, Jingsheng
author_sort Zhang, Youming
collection PubMed
description 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 mono- or di-methyl groups between the donors and acceptor could result in the spatial configuration changing greatly for 2MeTPA-QBT and TPA-QBT-MeTPA compared to their parent compound 2TPA-QBT. The emission of TPA-QBT-MeTPA 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 2TPA-QBT, 2MeTPA-QBT and TPA-QBT-MeTPA, 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 2TPA-QBT, 2MeTPA-QBT and TPA-QBT-MeTPA-doped OLEDs, respectively. This work illustrated the effect of spatial configuration changes on the luminescence properties of donor-acceptor-type organic emitters.
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spelling pubmed-85883532021-11-13 High Performance Near-Infrared Emitters with Methylated Triphenylamine and Thiadiazolo[3,4-g]quinoxaline-Based Fluorophores Zhang, Youming Wu, Chengjun Zhu, Minrong Miao, Jingsheng Molecules Article 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 mono- or di-methyl groups between the donors and acceptor could result in the spatial configuration changing greatly for 2MeTPA-QBT and TPA-QBT-MeTPA compared to their parent compound 2TPA-QBT. The emission of TPA-QBT-MeTPA 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 2TPA-QBT, 2MeTPA-QBT and TPA-QBT-MeTPA, 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 2TPA-QBT, 2MeTPA-QBT and TPA-QBT-MeTPA-doped OLEDs, respectively. This work illustrated the effect of spatial configuration changes on the luminescence properties of donor-acceptor-type organic emitters. MDPI 2021-10-22 /pmc/articles/PMC8588353/ /pubmed/34770795 http://dx.doi.org/10.3390/molecules26216386 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zhang, Youming
Wu, Chengjun
Zhu, Minrong
Miao, Jingsheng
High Performance Near-Infrared Emitters with Methylated Triphenylamine and Thiadiazolo[3,4-g]quinoxaline-Based Fluorophores
title 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_short 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
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8588353/
https://www.ncbi.nlm.nih.gov/pubmed/34770795
http://dx.doi.org/10.3390/molecules26216386
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