Synthesis, properties, and application of phenanthrenone: an undeveloped building block and a photocatalyst

Gan, Zhixing; Zhou, Jie; Zhu, Linsheng; Chen, Xinyu; Ma, Qiang; Yan, Jun‐Min; Liao, Saihu; Li, Yuanming

doi:10.1039/d3qo00775h

Org. Chem. Front.

2023

DOI: 10.1039/d3qo00775h

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Synthesis, properties, and application of phenanthrenone: an undeveloped building block and a photocatalyst

Zhixing Gan¹,

Jie Zhou²,

Linsheng Zhu³

et al.

Abstract: The synthesis, properties, and application of carbonyl-bridged phenanthrene, namely phenanthrenone are described. A new synthetic route involving palladium-catalyzed annulation between 4,5-dibromo-9-fluorenone and internal alkynes was developed to simplify the synthesis...

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2024

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Cited by 4 publications

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“…The bay-region annulative π-extension (APEX) of biphenyl is one of the effective synthetic strategies for the preparation of π-conjugated molecules and enables the fusion of diverse structural units and functional groups through easy and cost-effective synthetic routes. Representative examples include imide-functionalized fluorenone, biphenyl diimide, phenanthrenone, heteroatom-bridged heterofluorenes, and more . Among them, 4,5-silylene-bridged silafluorene plays a crucial role in APEX reactions for the construction of π-conjugated molecules .…”

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Synthesis, Characterization, and Properties of Sila-Annulated Phenanthrene Imides

Wu,

Shi,

Zhu

et al. 2024

Org. Lett.

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A series of sila-annulated phenanthrene imides were synthesized through a three-step synthetic route, which represent a hybrid class of biphenyl-based π-conjugated molecules incorporating an imide unit and silole. A comprehensive investigation of their structural, photophysical, and electronic properties was studied by experiment and theoretical calculations. Notably, sila-annulated phenanthrene imides with significant aggregation-induced emission (AIE) properties were observed.

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mentioning

confidence: 99%

Synthesis, Characterization, and Properties of Sila-Annulated Phenanthrene Imides

Wu,

Shi,

Zhu

et al. 2024

Org. Lett.

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Third-order nonlinear optics and optical limiting of phenanthrenone derivatives

Chen,

Zhu,

Zhang

et al. 2024

Dyes and Pigments

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Redox- and Charge-State Dependent Trends in 5, 6, and 7-Membered Boron Heterocycles: A Neutral Ligand Coordination Chemistry Approach to Boracyclic Cations, Anions, and Radicals

Hollister,

Wentz,

Gilliard

2024

Acc. Chem. Res.

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Metrics & MoreArticle Recommendations CONSPECTUS: Boron heterocycles represent an important subset of heteroatom-incorporated rings, attracting attention from organic, inorganic, and materials chemists. The empty p z orbital at the boron center makes them stand out as quintessential Lewis acidic molecules, also serving as a means to modulate electronic structure and photophysical properties in a facile manner. As boracycles are ripe for extensive functionalization, they are used in catalysis, chemical biology, materials science, and continue to be explored as chemical synthons for conjugated materials and reagents.Neutral boron(III)-incorporated polycyclic molecules are some of the most studied types of boracycles, and understanding their redox transformations is important for applications relying on electron transfer and charge transport. While relevant redox species can often be electrochemically observed, it remains challenging to isolate and characterize boracycles where the boron center and/or polycyclic skeleton have been chemically reduced. We describe our recent work isolating 5-, 6-, and 7-membered boracyclic radicals, anions, and cations, focusing on stabilization strategies, ligand-mediated bonding situations, and reactivity. We present a versatile neutral ligand coordination chemistry approach that permits the transformation of boracycles from potent electrophiles to powerful nucleophilic heterocycles that facilitate diverse electron transfer and bond activation chemistry. Although there are a wide range of suitable stabilizing ligands, we have employed both diamino-N-heterocyclic carbenes (NHCs) and cyclic(alkyl)(amino) carbenes (CAACs), which led to boracycles with tunable electronic structures and aromaticity trends. We highlight successful isolation of borafluorene radicals and demonstrate their reversible redox behavior, undergoing oxidation to the cation or reduction to the anion. The borafluorene anion is a chemical synthon that has been used to prepare boryl main-group and transition-metal bonds, luminescent oxabora-spirocycles, borafluorenate-crown ethers, and CO-releasing molecules via carbon dioxide activation. We expanded to 6-membered boracycles and characterized neutral bis(NHC-supported 9-boraphenanthrene)s and the corresponding bis(CAAC-stabilized 9-boraphenanthrene) biradical. We detail the interconvertible multiredox states of boraphenalene, where the boraphenalenyl radical, anion, and cation mimic the charge-states of the all-hydrocarbon analogue. Reactivity studies of the boraphenalenyl anion displayed unusual nucleophilic reactivity at multiple sites on the periphery of the boraphenalenyl tricyclic scaffold. Reduced borepins, 7-membered boron containing heterocycles, have also been isolated. We used a stepwise one-pot synthesis combining the halo-borepin precursor, CAAC, and KC 8 to afford the monomeric borepin radicals and anions. The π-system was extended to contain two borepin rings fused in a pentacyclic scaffold, which permitted isolation of diborepin biradicals and a diborep...

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Synthesis, properties, and application of phenanthrenone: an undeveloped building block and a photocatalyst

Abstract: The synthesis, properties, and application of carbonyl-bridged phenanthrene, namely phenanthrenone are described. A new synthetic route involving palladium-catalyzed annulation between 4,5-dibromo-9-fluorenone and internal alkynes was developed to simplify the synthesis...

Cited by 4 publications

References 65 publications

Synthesis, Characterization, and Properties of Sila-Annulated Phenanthrene Imides

Synthesis, Characterization, and Properties of Sila-Annulated Phenanthrene Imides

Third-order nonlinear optics and optical limiting of phenanthrenone derivatives

Redox- and Charge-State Dependent Trends in 5, 6, and 7-Membered Boron Heterocycles: A Neutral Ligand Coordination Chemistry Approach to Boracyclic Cations, Anions, and Radicals

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