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  1. Article ; Online: Discovery of Organic Optoelectronic Materials Powered by Oxidative Ar-H/Ar-H Coupling.

    Yang, Yudong / Wu, Yimin / Bin, Zhengyang / Zhang, Cheng / Tan, Guangying / You, Jingsong

    Journal of the American Chemical Society

    2024  Volume 146, Issue 2, Page(s) 1224–1243

    Abstract: Efficient and streamlined synthetic methods that facilitate the rapid build-up of structurally diverse π-conjugated systems are of paramount importance in the quest for organic optoelectronic materials. Among these methods, transition-metal-catalyzed ... ...

    Abstract Efficient and streamlined synthetic methods that facilitate the rapid build-up of structurally diverse π-conjugated systems are of paramount importance in the quest for organic optoelectronic materials. Among these methods, transition-metal-catalyzed oxidative Ar-H/Ar-H coupling reactions between two (hetero)arenes have emerged as a concise and effective approach for generating a wide array of bi(hetero)aryl and fused heteroaryl structures. This innovative approach bypasses challenges associated with substrate pre-activation processes, thereby allowing for the creation of frameworks that were previously beyond reach using conventional Ar-X/Ar-M coupling reactions. These inherent advantages have ushered in new design patterns for organic optoelectronic molecules that deviate from traditional methods. This ground-breaking approach enables the transcendence of the limitations of repetitive material structures, ultimately leading to the discovery of novel high-performance materials. In this Perspective, we provide an overview of recent advances in the development of organic optoelectronic materials through the utilization of transition-metal-catalyzed oxidative Ar-H/Ar-H coupling reactions. We introduce several notable synthetic strategies in this domain, covering both
    Language English
    Publishing date 2024-01-03
    Publishing country United States
    Document type Journal Article ; Review
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.3c12234
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Boron-Dipyrromethene-Based Fluorescent Emitters Enable High-Performance Narrowband Red Organic Light-Emitting Diodes.

    Liu, Jiahui / Liu, Junjie / Li, Haoyuan / Bin, Zhengyang / You, Jingsong

    Angewandte Chemie (International ed. in English)

    2023  Volume 62, Issue 31, Page(s) e202306471

    Abstract: Narrowband organic light-emitting diodes (OLEDs) are receiving significant attention and have demonstrated impressive performance in blue and green OLEDs. However, developing high-performance narrowband red OLEDs remains a highly desired yet challenging ... ...

    Abstract Narrowband organic light-emitting diodes (OLEDs) are receiving significant attention and have demonstrated impressive performance in blue and green OLEDs. However, developing high-performance narrowband red OLEDs remains a highly desired yet challenging task. Herein, we have developed narrowband red fluorescent emitters by utilizing a boron-dipyrromethene (BODIPY) skeleton in combination with a methyl-shield strategy. These emitters exhibit small full-width at half-maxima (FWHM) ranging from 21 nm (0.068 eV) to 25 nm (0.081 eV) and high photoluminescence quantum yields (Φ
    Language English
    Publishing date 2023-06-26
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202306471
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  3. Article ; Online: Structurally Nontraditional Bipolar Hosts for RGB Phosphorescent OLEDs: Boosted by a "Butterfly-Shaped" Medium-Ring Acceptor.

    Ma, Weixin / Bin, Zhengyang / Yang, Ge / Liu, Junjie / You, Jingsong

    Angewandte Chemie (International ed. in English)

    2022  Volume 61, Issue 11, Page(s) e202116681

    Abstract: The emitting layer based on a host-guest system plays a crucial role in organic light-emitting diodes (OLEDs). While emitters have witnessed rapid progress in structural diversity, hosts still rely heavily on traditional structures and are underdeveloped. ...

    Abstract The emitting layer based on a host-guest system plays a crucial role in organic light-emitting diodes (OLEDs). While emitters have witnessed rapid progress in structural diversity, hosts still rely heavily on traditional structures and are underdeveloped. Herein a "medium-ring" strategy has been put forward to design structurally nontraditional host molecules, which are not only rotatable enough to suppress close π-π stacking, thus reducing exciton annihilation, but also rigid enough to prevent excessive conformational flipping, thus inhibiting non-radiative decay. Accordingly, a brand-new type of bipolar hosts with a twisted "butterfly-shaped heptagonal acceptor (EtBP), which features an electron-deficient benzophenone fragment with a flexible ethylidene bridge, has been developed. With satisfactory morphological stability and well-balanced hole- and electron-transporting properties, the EtBP-based bipolar hosts enable high-performance RGB phosphorescent OLEDs with small efficiency roll-off, which are superior to those of acyclic benzophenone-based devices.
    Language English
    Publishing date 2022-02-01
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202116681
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  4. Article ; Online: Dipole moment engineering enables universal B-N-embedded bipolar hosts for OLEDs: an old dog learns a new trick.

    He, Shuang / Liu, Junjie / Yang, Ge / Bin, Zhengyang / You, Jingsong

    Materials horizons

    2022  Volume 9, Issue 11, Page(s) 2818–2823

    Abstract: Here, we carried out a dipole moment engineering to convert a classical BN-PAH framework into a formal acceptor for the construction of bipolar OLED host materials, with this engineering involving the introduction of two "donor wings". The installation ... ...

    Abstract Here, we carried out a dipole moment engineering to convert a classical BN-PAH framework into a formal acceptor for the construction of bipolar OLED host materials, with this engineering involving the introduction of two "donor wings". The installation of the donors transformed the small local dipole moment of the BN-PAH framework into a large charge-transfer dipole moment, leading to a more separated frontier molecular orbital distribution beneficial for bipolar transport as well as a higher glass-transition temperature beneficial for morphological stability. The assembled donor-acceptor-donor (D-A-D) triads exhibited promising potential as universal bipolar hosts for the fabrication of OLEDs of various categories with wide color gamuts, such as blue multiple-resonance OLEDs (MR-OLEDs), green thermally activated delayed-fluorescence OLEDs (TADF-OLEDs), yellow TADF-sensitized fluorescence OLEDs (TSF-OLEDs), and red phosphorescence OLEDs (Ph-OLEDs).
    Language English
    Publishing date 2022-10-31
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2744250-0
    ISSN 2051-6355 ; 2051-6347
    ISSN (online) 2051-6355
    ISSN 2051-6347
    DOI 10.1039/d2mh00856d
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Intramolecular C-H Activation as an Easy Toolbox to Synthesize Pyridine-Fused Bipolar Hosts for Blue Organic Light-Emitting Diodes.

    Wang, Fei / Zhang, Luoqiang / Han, Weiguo / Bin, Zhengyang / You, Jingsong

    Angewandte Chemie (International ed. in English)

    2022  Volume 61, Issue 32, Page(s) e202205380

    Abstract: The development of high-performance blue organic light-emitting diodes (OLEDs) remains a challenging task. While exploiting new blue emitters has attracted great interest, developing host materials that considerably determine device performance obviously ...

    Abstract The development of high-performance blue organic light-emitting diodes (OLEDs) remains a challenging task. While exploiting new blue emitters has attracted great interest, developing host materials that considerably determine device performance obviously lags behind. Herein, we present an ease of access to the structurally diverse benzoheteroaromatic-fused pyridine skeletons by the iridium-catalyzed intramolecular C-H/C-H coupling reaction, which unlocks an unparalleled opportunity to rapidly assemble a library of pyridine-fused bipolar host materials. As an illustrated example, the benzo[4,5]thieno[2,3-b]pyridine skeleton (BTP) has been made to a pseudo-symmetric host (DCz-BTP). The merging of a pyridine fragment enables strong intermolecular interactions, leading to satisfactory bipolar transporting properties. Utilizing DCz-BTP as the host, blue thermally activated delayed fluorescent OLEDs (TADF-OLEDs) exhibit a low turn-on voltage of 2.8 V and a high maximum external quantum efficiency (EQE
    Language English
    Publishing date 2022-06-21
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202205380
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  6. Article: Molecular engineering of locked alkyl aryl carbonyl-based thermally activated delayed fluorescence emitters

    Zhang, Yunxi / Huang, Zhengmei / Yang, Yudong / Liu, Jiahui / Tian, Yang / Bin, Zhengyang / You, Jingsong

    Chemical science

    2023  Volume 14, Issue 19, Page(s) 5125–5131

    Abstract: While diaryl ketones have drawn tremendous attention for the assembly of carbonyl-based thermally activated delayed fluorescence (TADF) emitters, alkyl aryl ketones are almost ignored. In this work, an efficient rhodium-catalyzed cascade C-H activation ... ...

    Abstract While diaryl ketones have drawn tremendous attention for the assembly of carbonyl-based thermally activated delayed fluorescence (TADF) emitters, alkyl aryl ketones are almost ignored. In this work, an efficient rhodium-catalyzed cascade C-H activation process of alkyl aryl ketones with phenylboronic acids has been developed for the concise construction of the α,α-dialkyl/aryl phenanthrone skeleton, which unlocks an opportunity to rapidly assemble a library of structurally nontraditional locked alkyl aryl carbonyl-based TADF emitters. Molecular engineering indicates that the introduction of a donor on the A ring enables the emitters to exhibit better TADF properties than those with a donor on the B ring. 2,6-Bis(9,9-dimethylacridin-10(9
    Language English
    Publishing date 2023-04-18
    Publishing country England
    Document type Journal Article
    ZDB-ID 2559110-1
    ISSN 2041-6539 ; 2041-6520
    ISSN (online) 2041-6539
    ISSN 2041-6520
    DOI 10.1039/d3sc01298k
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Alignment of Heptagonal Diimide and Triazine Enables Narrowband Pure-Blue Organic Light-Emitting Diodes with Low Efficiency Roll-Off.

    Han, Weiguo / Liu, Junjie / Ran, Chunhao / Huang, Zhenmei / Gao, Ge / You, Jingsong / Bin, Zhengyang

    Angewandte Chemie (International ed. in English)

    2023  Volume 62, Issue 48, Page(s) e202312297

    Abstract: The endeavor to develop high-performance narrowband blue organic light-emitting diodes (OLEDs) with low efficiency roll-off represents an attractive challenge. Herein, we introduce a hetero-acceptor design strategy centered around the heptagonal diimide ( ...

    Abstract The endeavor to develop high-performance narrowband blue organic light-emitting diodes (OLEDs) with low efficiency roll-off represents an attractive challenge. Herein, we introduce a hetero-acceptor design strategy centered around the heptagonal diimide (BPI) building block to create an efficient thermally activated delayed fluorescence (TADF) sensitizer. The alignment of a twisted BPI unit and a planar diphenyltriazine (TRZ) fragment imparts remarkable exciton dynamic properties to 26tCz-TRZBPI, including a fast radiative decay rate (k
    Language English
    Publishing date 2023-10-23
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202312297
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  8. Article ; Online: Medium-Ring Strategy Enables Multiple Resonance Emitters with Twisted Geometry and Fast Spin-Flip to Suppress Efficiency Roll-Off.

    Lei, Bowen / Huang, Zhenmei / Li, Songtao / Liu, Junjie / Bin, Zhengyang / You, Jingsong

    Angewandte Chemie (International ed. in English)

    2023  Volume 62, Issue 12, Page(s) e202218405

    Abstract: Suppressing aggregation-caused quenching (ACQ) effect and reducing device efficiency roll-off are both crucial yet challenging for multi-resonance (MR) emitters. Herein, we put forward a medium-ring strategy to design efficient MR emitters that feature ... ...

    Abstract Suppressing aggregation-caused quenching (ACQ) effect and reducing device efficiency roll-off are both crucial yet challenging for multi-resonance (MR) emitters. Herein, we put forward a medium-ring strategy to design efficient MR emitters that feature heptagonal tribenzo[b,d,f]azepine (TBA) donors. The highly twisted conformation enlarges the intermolecular distances between the MR-emitting cores, and thus suppresses ACQ effect. Meanwhile, the introduction of heptagonal donors enhances spin-orbital coupling, so as to accelerate reverse intersystem crossing (RISC) process. This medium-ring strategy gives rise to the first example of blue MR emitter that simultaneously possesses radiative decay rate as fast as 10
    Language English
    Publishing date 2023-02-14
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202218405
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  9. Article ; Online: Unlocking Structurally Nontraditional Naphthyridine-Based Electron-Transporting Materials with C-H Activation-Annulation.

    Luo, Anping / Bao, Yuanyuan / Liu, Xiaoyu / Liu, Junjie / Han, Weiguo / Yang, Ge / Yang, Yudong / Bin, Zhengyang / You, Jingsong

    Journal of the American Chemical Society

    2024  Volume 146, Issue 9, Page(s) 6240–6251

    Abstract: The inherent benefits of C-H activation have given rise to innovative approaches in designing organic optoelectronic molecules that depart from conventional methods. While theoretical calculations have suggested the suitability of the 2,6-naphthyridine ... ...

    Abstract The inherent benefits of C-H activation have given rise to innovative approaches in designing organic optoelectronic molecules that depart from conventional methods. While theoretical calculations have suggested the suitability of the 2,6-naphthyridine scaffold for electron transport materials (ETMs) in organic light-emitting diodes (OLEDs), the existing synthetic methodologies have proven to be insufficient for the construction of multiple arylated and fully aryl-substituted molecules. Herein, we present a solution for the synthesis of 2,6-naphthyridine derivatives, with the rhodium-catalyzed consecutive C-H activation-annulation process of fumaric acid with alkynes standing as the pivotal step within this strategy. The ETMs, purposefully designed and synthesized based on the 2,6-naphthyridine framework, exhibit an impressively high glass-transition temperature (
    Language English
    Publishing date 2024-02-05
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.3c14297
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article ; Online: Concise Synthesis of Polysubstituted Carbohelicenes by a C-H Activation/Radical Reaction/C-H Activation Sequence.

    Yin, Jiangliang / You, Jingsong

    Angewandte Chemie (International ed. in English)

    2018  Volume 58, Issue 1, Page(s) 302–306

    Abstract: Disclosed herein is the merging of C-H activation and radical chemistry, enabling rapid access to a structurally diverse family of fused carbohelicenes through the fusion of α-acetylnaphthalenes with alkynes under oxidative conditions. This cascade ... ...

    Abstract Disclosed herein is the merging of C-H activation and radical chemistry, enabling rapid access to a structurally diverse family of fused carbohelicenes through the fusion of α-acetylnaphthalenes with alkynes under oxidative conditions. This cascade process exhibits exquisite chemoselectivity and regioselectivity. The reaction pathway was analyzed by intermediate separations, control experiments, radical trapping, EPR, MALDI-TOF-MS, and ESI-HRMS experiments, and shown to involve a C2-H activation/radical reaction/C8-H activation relay.
    Language English
    Publishing date 2018-11-28
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.201811023
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