Condensed Osmaquinolines with NIR‐II Absorption Synthesized by Aryl C−H Annulation and Aromatization DOI
Fei‐Hu Cui, Qian Li, Le‐Han Gao

et al.

Angewandte Chemie, Journal Year: 2022, Volume and Issue: 134(48)

Published: Oct. 3, 2022

Abstract The structural design and tuning of properties metallaaromatics are crucial in materials energy science. Herein, we describe the rapid synthesis tetracyclic containing quinoline pentalene motifs fused by a metal‐bridged fragment. These unique compounds display remarkably broad absorption, enabling for first time absorption to reach second near‐infrared (NIR‐II) bio‐window. formation osmaquinoline unit involves an unconventional C(sp 2 )−C(sp 3 ) coupling promoted AgBF 4 achieve [3+3] cycloaddition. introduction cyclic d π ‐p conjugation extension aromatic π‐framework can effectively shrink HOMO–LUMO gap, thus broadening window. considerable photothermal conversion efficiency (PCE) both NIR‐I NIR‐II windows, high stability excellent electrochemical behavior suggest many potential applications these condensed metallaquinolines.

Language: Английский

Condensed Osmaquinolines with NIR‐II Absorption Synthesized by Aryl C−H Annulation and Aromatization DOI
Fei‐Hu Cui, Qian Li, Le‐Han Gao

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(48)

Published: Oct. 3, 2022

The structural design and tuning of properties metallaaromatics are crucial in materials energy science. Herein, we describe the rapid synthesis tetracyclic containing quinoline pentalene motifs fused by a metal-bridged fragment. These unique compounds display remarkably broad absorption, enabling for first time absorption to reach second near-infrared (NIR-II) bio-window. formation osmaquinoline unit involves an unconventional C(sp2 )-C(sp3 ) coupling promoted AgBF4 achieve [3+3] cycloaddition. introduction cyclic dπ -pπ conjugation extension aromatic π-framework can effectively shrink HOMO-LUMO gap, thus broadening window. considerable photothermal conversion efficiency (PCE) both NIR-I NIR-II windows, high stability excellent electrochemical behavior suggest many potential applications these condensed metallaquinolines.

Language: Английский

Citations

16
Fusion of Four Aromatic Rings via an Atom-Mutual-Embedding Strategy to Form a Tetrahexacyclic System DOI
Fei‐Hu Cui, Le‐Han Gao,

Kaidong Ruan

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

Skeletal manipulation of aromatic compounds has emerged as a potent tool in synthetic chemistry, but simultaneous multiring remains largely unexplored due to the inherent complexities ring and site selectivity. Herein, we report an unprecedented skeletal that fuses four 5-membered rings, comprising two organic metal-containing systems, into novel metal-bridged 6/6/6/6-membered scaffold. The sequential fusion is accomplished through atom-mutual-embedding strategy; this strategy entails stepwise insertion nitrogen atoms separate metal-carbon bonds simultaneously integrates metal atom bridge across isoxazole moieties. presence central crucial for ensuring precise substrate alignment enhancing both specificity. resulting tetrahexacyclic products exhibit remarkable stability superior near-infrared (NIR) functional properties, surpassing those precursor compounds. This work not only establishes conceptual foundation designing versatile molecules amenable intricate editing also contributes rational performance-targeted molecular architectures.

Language: Английский

Citations

0
Nitrogen-Based Organofluorine Functional Molecules: Synthesis and Applications DOI
Shuai Liu, Jun Zhou, Lu Yu

et al.

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Fluorine and nitrogen form a successful partnership in organic synthesis, medicinal chemistry, material sciences. Although fluorine-nitrogen chemistry has long rich history, this field received increasing interest made remarkable progress over the past two decades, driven by recent advancements transition metal organocatalysis photochemistry. This review, emphasizing contributions from 2015 to 2023, aims update state of art synthesis applications nitrogen-based organofluorine functional molecules chemistry. In dedicated sections, we first focus on fluorine-containing reagents organized according type groups attached nitrogen, including N-F, N-RF, N-SRF, N-ORF. review also covers nitrogen-linked building blocks, catalysts, pharmaceuticals, agrochemicals, underlining these components' broad applicability growing importance modern

Language: Английский

Citations

0
Mechanistic Insights into Alkylated and Polycyclic N-Heterocycle Formation from Aromatic Amino Acids during Hydrothermal Liquefaction DOI
Hanifrahmawan Sudibyo,

Sebastian B. Pangaribuan,

Liska D. Muktiarani

et al.

Energy & Fuels, Journal Year: 2025, Volume and Issue: unknown

Published: May 28, 2025

Language: Английский

Citations

0
Copper-catalyzed C(sp)–H aryl amination enables modular synthesis of quinolines and 2-quinolinones DOI
Yang Gao, Haixia Li, Simin Yang

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 67(2), P. 595 - 603

Published: Oct. 23, 2023

Language: Английский

Citations

8
NiH-Catalyzed Proximal-Selective Hydroamination of Unactivated Alkenes with Anthranils DOI

Yushan Cui,

Yang Gao,

Wanxuan Zhao

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14861 - 14869

Published: Oct. 11, 2022

The regioselective hydroamination of unactivated alkenes is a long-standing challenge in organic synthesis. Herein, we report NiH-catalyzed proximal-selective with 8-aminoquinoline (AQ) as bidentate auxiliary and anthranils aminating reagents. A wide range primary aryl amines bearing an ortho-carbonyl group were installed both terminal internal alkenes, delivering variety valuable β- γ-amino acid building blocks, respectively, excellent regiocontrol. utility this transformation was further demonstrated by the conversion multifunctionalized into useful N-heterocycles.

Language: Английский

Citations

11
Ag-Catalyzed Practical Synthesis of N-Acyl Anthranilic Acids from Anthranils and Carboxylic Acids DOI
Changshu Wu, Yang Gao, Yanping Huo

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3150 - 3160

Published: Feb. 9, 2024

A practical synthesis of valuable N-acyl anthranilic acids has been achieved via a silver-catalyzed imino-ketene generation from readily available anthranils and carboxylic acids. wide range including sterically demanding aliphatic acids, aromatic acrylic amino are compatible in this reaction. Moreover, method can be used to modify drug molecules natural products, such as ibuprofen, probenecid, acetylglycine.

Language: Английский

Citations

2
Synthesis of 4-styrylquinolines via direct oxidative C3-alkenylation of anthranils under Pd(ii) catalysis DOI

Annapurna Awasthi,

Khushboo Tiwari,

Pushpendra Yadav

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(15), P. 2054 - 2057

Published: Jan. 1, 2024

The palladium-catalyzed oxidative C3-alkenylation of anthranils (2,1-benzisoxazoles) with various styrenes has been successfully achieved.

Language: Английский

Citations

1
Triflic Acid-Mediated Chemoselective Indole C2-Heteroarylation of Peptide Tryptophan Residues by Triazine DOI
Jian Li, Qi-Long Hu,

Jia-Shu Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 9, 2024

Peptide modification provides opportunities to afford peptides with designed functions. Among the proteogenic amino acids, tryptophan represents an ideal and attractive target for peptide because of exclusive chemical reactivity its unique indole structure. Herein, we reported C2 position-selective transition-metal-free approach derivatives tryptophan-containing by triazine via triflic acid activation that incorporated functional group could act as orthogonal handle further bioconjugation inverse electron demand Diels–Alder reaction.

Language: Английский

Citations

1
Electrochemical Site-Selective Alkylation of Azobenzenes with (Thio)Xanthenes DOI Creative Commons

Qiang Zhong,

Hui Gao, Pei-Long Wang

et al.

Molecules, Journal Year: 2022, Volume and Issue: 27(15), P. 4967 - 4967

Published: Aug. 4, 2022

Herein, we first report an electrochemical methodology for the site-selective alkylation of azobenzenes with (thio)xanthenes in absence any transition metal catalyst or external oxidant. A variety groups are compatible this alkylation, which furnishes products moderate to good yields.

Language: Английский

Citations

6