Two N,N-chelated difluoroboron complexes containing phenanthroimidazole moiety: Synthesis and luminescence properties

Li, Xinyu; Tang, Pengyu; Yu, Tianzhi; Su, Wenming; Li, Yanmei; Wang, Youjia; Zhang, Xiaochen; Zhang, Hui

doi:10.1016/j.dyepig.2018.11.032

Cited by 14 publications

(4 citation statements)

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“…Secondly, the ligand 9‐(4‐(6‐(1 H ‐benzo[ d ]imidazol‐2‐yl)pyridin‐2‐yl)phenyl)‐9 H ‐carbazole ( 2 ) and 9‐(3‐(6‐(1 H ‐benzo[ d ]imidazol‐2‐yl)pyridin‐2‐yl)phenyl)‐9 H ‐carbazole ( 3 ) were prepared by treating 1 with the corresponding phenylcarbazole boric acid (4‐ and 3‐positions) via classical Pd‐catalyzed Suzuki‐Miyaura coupling reaction according to literature procedure . Finally, the complexes B1PCz and B1MCz could be obtained by treating the ligand 2 or 3 with boron trifluoride etherate (BF3⋅Et2O) using triethylamine (Et 3 N) or ethyldiisopropylamine (DIEA) as base . The key intermediates 2 and 3 and the target products B1PCz and B1MCz were fully characterized by nuclear magnetic resonance (NMR), mass spectrometry (MS) and elemental analysis (EA).…”

Section: Resultsmentioning

confidence: 99%

“…B1PCz and B1MCz were synthesized from a modification of reported procedures, except that 2 or 3 as the reagent.…”

Section: Methodsmentioning

confidence: 99%

“…Three‐coordinate organoboron compounds for OLED applications have been widely studied, such as acting as host materials (Figure ), hole blocking materials, electron transport materials, emission materials, as well as thermally activated delayed fluorescent (TADF) materials . On the other hand, four‐coordinate organoboron compounds are also widely applied as OLED materials such as hole blocking materials, emission materials (NNFF−, NCOO−, CCNO−,– CCNN−, and OOFF−type chelate ligands), and TADF materials (such as NNNO−, NNOO−, OOFF−, CCCN−,– and CCNO‐type chelate ligands) . However, four‐coordinate organoboron compounds serving as host materials for OLEDs is rarely reported up to now.…”

Section: Introductionmentioning

confidence: 99%

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Four‐Coordinate Organoboron Platforms for Efficient Red Phosphorescent Organic Light‐Emitting Diodes

et al. 2019

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So far both three‐ and four‐coordinate organoboron compounds have been widely applied in organic light‐emitting diode (OLED) materials. However, the use of four‐coordinate organoboron compounds as host materials is rarely reported. In this work, two new four‐coordinate organoboron compounds, namely 8‐(4‐(9H‐carbazol‐9‐yl)phenyl)‐6,6‐difluoro‐6H‐6λ4,7λ4‐benzo[4′,5′]imidazo[1′,2′:3,4][1,3,2]diazaborolo[1,5‐a]pyridine (B1PCz) and 8‐(3‐(9H‐carbazol‐9‐yl)phenyl)‐6,6‐difluoro‐6H‐6λ4,7λ4‐benzo[4′,5′]imidazo[1′,2′:3,4][1,3,2]diazaborolo[1,5‐a]pyridine (B1MCz), were successfully designed, synthesized, and fully characterized. The red OLEDs using B1PCz and B1MCz as host materials achieved relatively high device performance with a maximum external quantum efficiency of 14.8 % and 11.8 %, respectively. These results will expand the scope of organoboron compounds for OLED materials and reveal the great potential of four‐coordinate organoboron materials.

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Section: Resultsmentioning

confidence: 99%

“…B1PCz and B1MCz were synthesized from a modification of reported procedures, except that 2 or 3 as the reagent.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Four‐Coordinate Organoboron Platforms for Efficient Red Phosphorescent Organic Light‐Emitting Diodes

et al. 2019

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“…Thus, they could be used as a material in many fields. For this purpose, in addition to dipyrromethene derivatives, benzimidazoles, 9 hydrazine-bispyrrole (BOPHY), 10 anilidoimine 11 ligands have been studied as the N,N-chelated difluoroboron complexes because of the promising luminescent properties so far. Among the compounds studied with this aim, BF 2 complexes of Schiff-base ligands have been presented in a few studies as the N,Ochelated difluoroboron complexes.…”

Section: Introductionmentioning

confidence: 99%

A highly fluorescent tri-nuclear boron complex with large Stokes shifts based on tripodal Schiff base: synthesis and photophysical properties

Şen

2019

J Chem Sci

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In this study, a new imine-based tripodal ligand and its difluoroboron complex were designed and synthesized. This trinuclear-boron complex was prepared for the first time and fully characterized by common spectroscopic techniques such as 1 H-NMR, 13 C-NMR, FT-IR, UV-Vis and MS analysis. The optical and fluorescence properties of complex were examined in CHCl 3 , THF, acetonitrile, EtOAc, DMF and DMSO. It was revealed that the obtained boron complex showed intense emission with large Stokes shifts in the range from 83 nm to 96 nm. As a result of quantification of fluorescence quantum yields, it has been observed that it has high quantum yield values up to 48%. The large Stokes shifts and high efficient emissions in the solutions of boron complex make it precious fluorophore for potential applications in materials science.

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Ruthenium‐Catalyzed Double C(sp²)−H Functionalizations of Fumaramides with Alkynes for the Divergent Synthesis of Pyridones and Naphthyridinediones

Han

Zhang

et al. 2020

ChemCatChem

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Transition‐metal‐catalyzed C−H functionalization of aromatic secondary amides with alkynes mainly undergo C−H/N−H annulation but rarely undergo ortho‐alkenylation. It is particularly challenging to selectively realize both oxidative annulation and ortho‐alkenylation of aromatic secondary amides with alkynes in the transition‐metal‐catalysis. In this article, we synthesized fully‐substituted 2‐pyridones and 2,6‐naphthyridine‐1,5‐diones via C(sp2)−H functionalization of fumaramides for the first time. Under the Ru‐catalysis, fumaramides and 1,2‐diaryl ethynes first undergo C−H/N−H annulation leading to the intermediate 2‐pyridone with an exocyclic secondary amide, and subsequently undergo the unexpected stereoselective C−H alkenylation to realize fully substituted 2‐pyridones bearing an exocyclic anti alkenyl group. On the addition of K2CO3, however, the transformation of fumaramides with 1,2‐dialkyl ethyne undergoes two conventional C−H/N−H annulations to provide 2,6‐naphthyridine‐1,5‐diones in high yield. The two procedures can be successfully enlarged to gram‐scales without erosion of the yields. In addition, some 2‐pyridones and 2,6‐naphthyridine‐1,5‐diones emitting clear ultraviolent and fluorescent light, indicating the potential utility of this work in organic light‐emitting materials.

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Two N,N-chelated difluoroboron complexes containing phenanthroimidazole moiety: Synthesis and luminescence properties

Cited by 14 publications

References 41 publications

Four‐Coordinate Organoboron Platforms for Efficient Red Phosphorescent Organic Light‐Emitting Diodes

Four‐Coordinate Organoboron Platforms for Efficient Red Phosphorescent Organic Light‐Emitting Diodes

A highly fluorescent tri-nuclear boron complex with large Stokes shifts based on tripodal Schiff base: synthesis and photophysical properties

Ruthenium‐Catalyzed Double C(sp²)−H Functionalizations of Fumaramides with Alkynes for the Divergent Synthesis of Pyridones and Naphthyridinediones

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Two N,N-chelated difluoroboron complexes containing phenanthroimidazole moiety: Synthesis and luminescence properties

Cited by 14 publications

References 41 publications

Four‐Coordinate Organoboron Platforms for Efficient Red Phosphorescent Organic Light‐Emitting Diodes

Four‐Coordinate Organoboron Platforms for Efficient Red Phosphorescent Organic Light‐Emitting Diodes

A highly fluorescent tri-nuclear boron complex with large Stokes shifts based on tripodal Schiff base: synthesis and photophysical properties

Ruthenium‐Catalyzed Double C(sp2)−H Functionalizations of Fumaramides with Alkynes for the Divergent Synthesis of Pyridones and Naphthyridinediones

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Product

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Ruthenium‐Catalyzed Double C(sp²)−H Functionalizations of Fumaramides with Alkynes for the Divergent Synthesis of Pyridones and Naphthyridinediones