Advances on the Merger of Electrochemistry and Transition Metal Catalysis for Organic Synthesis

Chemical Reviews, Год журнала: 2021, Номер 122(3), С. 3180 - 3218

Опубликована: Ноя. 19, 2021

Synthetic organic electrosynthesis has grown in the past few decades by achieving many valuable transformations for synthetic chemists. Although electrocatalysis been popular improving selectivity and efficiency a wide variety of energy-related applications, last two decades, there much interest to develop conceptually novel transformations, selective functionalization, sustainable reactions. This review discusses recent advances combination electrochemistry homogeneous transition-metal catalysis synthesis. The enabling mechanistic studies are presented alongside advantages as well future directions address challenges metal-catalyzed electrosynthesis.

Язык: Английский

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Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Angewandte Chemie International Edition, Год журнала: 2019, Номер 59(8), С. 2998 - 3027

Опубликована: Июль 25, 2019

Oxidative aromatic coupling occupies a fundamental place in the modern chemistry of compounds. It is method choice for assembly large and bewildering architectures. Considerable effort was also devoted to applications Scholl reaction synthesis chiral biphenols natural products. The ability form biaryl linkages without any prefunctionalization provides an efficient pathway many complex structures. Although this process only now becoming fully understood, continues both fascinate challenge researchers. This especially true heterocoupling, that is, oxidative with chemoselective formation C-C bond between two different arenes. Analysis progress achieved field since 2013 reveals groups have contributed by pushing boundary structural possibilities, expanding into surface-assisted (cyclo)dehydrogenation, developing new reagents.

Язык: Английский

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Polycyclic aromatic hydrocarbons in the graphene era

Science China Chemistry, Год журнала: 2019, Номер 62(9), С. 1099 - 1144

Опубликована: Июнь 25, 2019

Polycyclic aromatic hydrocarbons (PAHs) have been the subject of interdisciplinary research in fields chemistry, physics, materials science, and biology. Notably, PAHs drawn increasing attention since discovery graphene, which has regarded as “wonder” material 21st century. Different from semimetallic nanoscale graphenes, such graphene nanoribbons quantum dots, exhibit finite band gaps owing to confinement, making them attractive semiconductors for next-generation electronic applications. Researches based on graphenes expanded rapidly over past decade, thereby posing a challenge conducting comprehensive review. This study aims interconnect mainly discussed separately. In particular, by selecting representative examples, we explain how these two domains can stimulate each other. We hope that this integrated approach offer new opportunities further promote synergistic developments fields.

Язык: Английский

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Nanographenes and Graphene Nanoribbons as Multitalents of Present and Future Materials Science

Journal of the American Chemical Society, Год журнала: 2022, Номер 144(26), С. 11499 - 11524

Опубликована: Июнь 7, 2022

As cut-outs from a graphene sheet, nanographenes (NGs) and nanoribbons (GNRs) are ideal cases with which to connect the world of molecules that bulk carbon materials. While various top-down approaches have been developed produce such nanostructures in high yields, present perspective, precision structural control is emphasized for length, width, edge structures NGs GNRs achieved by modern solution on-surface syntheses. Their possibilities further extended "flatland" three-dimensional world, where chirality handedness jewels crown. In addition properties exhibited at molecular level, self-assembly thin-film cannot be neglected, emphasizes importance processing techniques. With rich toolkit chemistry hand, can endowed versatile functions ranging stimulated emission spintronics bioimaging energy storage, thus demonstrating their multitalents future materials science.

Язык: Английский

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Construction of Heptagon‐Containing Molecular Nanocarbons

Angewandte Chemie International Edition, Год журнала: 2021, Номер 60(44), С. 23508 - 23532

Опубликована: Фев. 6, 2021

Abstract Molecular nanocarbons containing heptagonal rings have attracted increasing interest due to their dynamic behavior, electronic properties, aromaticity, and solid‐state packing. Heptagon incorporation can not only induce negative curvature within nanocarbon scaffolds, but also confer significantly altered properties through interaction with adjacent non‐hexagonal rings. Despite the disclosure of several beautiful examples in recent years, synthetic strategies toward heptagon‐embedded molecular remain relatively limited intrinsic challenges heptagon formation into polyarene frameworks. In this Review, advances solution‐mediated surface‐assisted synthesis heptagon‐containing nanocarbons, as well intriguing these frameworks, will be discussed.

Язык: Английский

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Infinitene: A Helically Twisted Figure-Eight [12]Circulene Topoisomer

Journal of the American Chemical Society, Год журнала: 2021, Номер 144(2), С. 862 - 871

Опубликована: Дек. 15, 2021

New forms of molecular nanocarbon particularly looped polyarenes adopting various topologies contribute to the fundamental science and practical applications. Here we report synthesis an infinity-shaped polyarene, infinitene (1) (cyclo[c.c.c.c.c.c.e.e.e.e.e.e]dodecakisbenzene), comprising consecutively fused 12-benzene rings forming enclosed loop with a strain energy 60.2 kcal·mol–1. Infinitene represents topoisomer still-hypothetical [12]circulene, its scaffold can be formally visualized as outcome "stitching" two homochiral [6]helicene subunits by both their ends. The synthetic strategy encompasses transformation rationally designed dithiacyclophane cyclophadiene through Stevens rearrangement pyrolysis corresponding S,S′-bis(oxide) followed photocyclization. structure 1 is unique hybrid helicene circulene formula C48H24, which regarded isomer for kekulene, [6,6]carbon nanobelt ([6,6]CNB), [12]cyclacene. bench-stable yellow solid green fluorescence soluble common organic solvents. Its figure-eight was unambiguously confirmed X-ray crystallography. significantly compressed manifested remarkably shortened distance (3.152–3.192 Å) between centroids π–π stacked central benzene closest C···C 2.920 Å. Fundamental photophysical properties were thoroughly elucidated UV–vis absorption spectroscopic studies density functional theory calculations. configurational stability enabled separation enantiomers (P,P) (M,M) chiral HPLC. Circular dichroism (CD) circularly polarized luminescence (CPL) measurements revealed that has moderate |gCD| |gCPL| values.

Язык: Английский

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Multilayer stacks of polycyclic aromatic hydrocarbons

Nature Chemistry, Год журнала: 2022, Номер 14(4), С. 457 - 462

Опубликована: Фев. 7, 2022

Язык: Английский

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Application of Palladium-Catalyzed C(sp2)–H Bond Arylation to the Synthesis of Polycyclic (Hetero)Aromatics

Chem, Год журнала: 2019, Номер 5(8), С. 2006 - 2078

Опубликована: Июль 3, 2019

Язык: Английский

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A Quest for Structurally Uniform Graphene Nanoribbons: Synthesis, Properties, and Applications

The Journal of Organic Chemistry, Год журнала: 2019, Номер 85(1), С. 4 - 33

Опубликована: Дек. 2, 2019

Graphene nanoribbons are the class of next-generation carbon materials that attracting many researchers in various research fields. Their unique properties, such as band gap, conductivity, carrier mobility, thermal spin polarization, and on–off behavior, heavily depend on structural factors edge structure, width, length. Therefore, synthesis graphene with control over these atomic precision is crucially important. Among synthetic approaches, bottom-up methods on-surface polymerizations solution-phase represent promising ways to length, structure nanoribbons. In this Perspective, we introduce recently reported for theoretical experimental those physical properties applications. Reviewing researches along highlighting advantages limitations, emphasize how structurally controlled important provides future outlooks nanoribbon science.

Язык: Английский

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Emerging Bottom‐Up Strategies for the Synthesis of Graphene Nanoribbons and Related Structures

Angewandte Chemie International Edition, Год журнала: 2019, Номер 59(12), С. 4624 - 4633

Опубликована: Июль 2, 2019

Abstract The solution‐phase synthesis is one of the most promising strategies for preparation well‐defined graphene nanoribbons (GNRs) in large scale. To prepare high quality, defect‐free GNRs, cycloaromatization reactions need to be very efficient, proceed without side reaction and mild enough accommodate presence various functional groups. In this Minireview, we present latest synthetic approaches GNRs related structures, including alkyne benzannulation, photochemical cyclodehydrohalogenation, Mallory Pd‐ Ni‐catalyzed reactions.

Язык: Английский

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