C–H activation-enabled synthesis of a piperazine-embedded azadibenzo[<i>a</i>,<i>g</i>]corannulene analogue

Huang, Lin; Qiu, Mengyu; Chang, Zhihao; Browne, Duncan L.; Huang, Jianhui

doi:10.1039/d4qo00415a

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00415a

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C–H activation-enabled synthesis of a piperazine-embedded azadibenzo[a,g]corannulene analogue

Lin Huang,

Mengyu Qiu,

Zhihao Chang

et al.

Abstract: A novel piperazine-embedded azadibenzo[a,g]corannulene analogue was synthesized by a four-step bottom-up synthesis, including a nucleophilic aromatic substitution (SNAr) and a palladium-catalyzed intramolecular C–H activation arylation as key steps. This intriguing...

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C─H Activation Enables the Construction of New Bis‐Polyaryl Phenylpyridine Ruthenium Complexes: Conjugation and Rigidity Synergistic Effect for Advanced Electrochemiluminescence

Malik,

Sun,

et al. 2024

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The access to bench‐stable organometallic compounds unfolds new chemical space for medicinal and material sciences. In particular, stable organoruthenium compounds with constitutional and stereoisomeric forms for subtle regulation of electrochemiluminescence are intriguing and challenging. Here, coordination of polycyclic aromatic hydrocarbons on (2‐phenylpyridine)2(CO)2Ru complex allows access to bis‐polyaryl phenylpyridine (BPP) Ruthenium complex through C─H activation strategy and coupling reactions for installation of the functionalities with steric and electronic purposes. The photoluminescence and electrochemiluminescence of BPP Ru complexes are affected by the actual polycyclic aromatic hydrocarbons inherent properties. The anthracene derivatized BPP Ru complex (BPP‐Ant) shows the best ECL performance and reveals an enormous ECL quantum efficiency of 1.6‐fold higher than the golden standard Ru(bpy)32+. The unprecedentedly high efficiency is due to the best compromise between the structural conjugation and molecular rigidity from BPP‐Ant providing a providential energy gap that facilitated the feasibility of electron transfer and favored the radiative energy release by experimentally and DFT calculations. Moreover, PL and spooling ECL spectroscopies are used to track and link multiple emission peaks of BPP‐Ant at 445, 645, and 845 nm to different emissive species. These discoveries will add a new member to the efficient ECL ruthenium complex family and bring more potentials.

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C─H Activation Enables the Construction of New Bis‐Polyaryl Phenylpyridine Ruthenium Complexes: Conjugation and Rigidity Synergistic Effect for Advanced Electrochemiluminescence

Malik,

Sun,

et al. 2024

Small

View full text Add to dashboard Cite

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Copper-promotedortho-directed C–H amination of 2-arylpyridines with NH-heterocycles

Zeng,

Dong

2024

Org. Biomol. Chem.

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C–H activation-enabled synthesis of a piperazine-embedded azadibenzo[a,g]corannulene analogue

Abstract: A novel piperazine-embedded azadibenzo[a,g]corannulene analogue was synthesized by a four-step bottom-up synthesis, including a nucleophilic aromatic substitution (SNAr) and a palladium-catalyzed intramolecular C–H activation arylation as key steps. This intriguing...

Cited by 2 publications

References 63 publications

C─H Activation Enables the Construction of New Bis‐Polyaryl Phenylpyridine Ruthenium Complexes: Conjugation and Rigidity Synergistic Effect for Advanced Electrochemiluminescence

C─H Activation Enables the Construction of New Bis‐Polyaryl Phenylpyridine Ruthenium Complexes: Conjugation and Rigidity Synergistic Effect for Advanced Electrochemiluminescence

Copper-promotedortho-directed C–H amination of 2-arylpyridines with NH-heterocycles

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