4.8 Article

The Regioselective Solid-State Photo-Mechanochemical Synthesis of Nanographenes with UV light

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Physical

Photomechanochemical control over stereoselectivity in the [2+2] photodimerization of acenaphthylene

Sankarsan Biswas et al.

Summary: Tuning solubility and mechanical activation can alter the stereoselectivity of the [2 + 2] photochemical cycloaddition reaction. The solid-state reaction and the reaction in organic solvents yield the anti and syn products, respectively. DFT calculations show that the solid-state reaction proceeds via a covalently bonded excimer, driving anti selectivity. Under photomechanochemical conditions, the noncovalently bound syn conformer experiences greater destabilization, leading to the formation of the syn product. This work demonstrates the viability of photomechanochemistry for the preparation of complex organic scaffolds.

FARADAY DISCUSSIONS (2023)

Article Chemistry, Multidisciplinary

Mechanochemical Solvent-Free Suzuki-Miyaura Cross-Coupling of Amides via Highly Chemoselective N-C Cleavage

Jin Zhang et al.

Summary: A highly chemoselective, solvent-free mechanochemical strategy for the cross-coupling of amides by N-C bond activation has been reported. The method shows excellent selectivity, functional group tolerance, and can be applied for late-stage functionalization of complex molecules. This extends the repertoire of N-C bond interconversions to solid-state environmentally friendly mechanochemical methods.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Multidisciplinary

Metal-Catalyzed Organic Reactions by Resonant Acoustic Mixing**

Lori Gonnet et al.

Summary: Resonant Acoustic Mixing (RAM) is a fast and operationally simple catalytic organic synthesis method that does not require bulk solvent or milling media. It allows for direct scaling up of reactions without significant changes in reaction conditions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Organic

Photo-Thermo-Mechanochemical Approach to Synthesize Quinolines via Addition/Cyclization of Sulfoxonium Ylides with 2-Vinylanilines Catalyzed by Iron(II) Phthalocyanine

Luyao Liu et al.

Summary: A novel photo-thermo-mechanochemical approach has been developed to assemble quinolines catalyzed by iron(II) phthalocyanine, featuring a cost-efficient catalytic system with operational simplicity and solvent-free conditions. Mechanistic experiments suggest that the in-situ-formed secondary amine may play a key role in the further cyclization/aromatization process.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

The Direct Mechanocatalytic Suzuki-Miyaura Reaction of Small Organic Molecules

Wilm Pickhardt et al.

Summary: This study achieved the molecular Suzuki cross-coupling reaction mechanochemically, without solvents, ligands, or catalyst powders. By using a catalytically active palladium milling ball, products were formed in quantitative yield in as little as 30 min. The adjustment of milling parameters eliminated abrasion from the catalyst ball and allowed for systematic catalyst analysis for the first time.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Multidisciplinary

SpeedMixing: Rapid Tribochemical Synthesis and Discovery of Pharmaceutical Cocrystals without Milling or Grinding Media

Yong Teoh et al.

Summary: This study presents a rapid blending technology called SpeedMixing for fast mechanosynthesis and discovery of model pharmaceutical cocrystals. The method utilizes rapid spinning in the absence of bulk solvents and milling/grinding media. Syntheses of pharmaceutical cocrystals based on different active pharmaceutical ingredients demonstrate that SpeedMixing is a rapid, scalable, controllable, and selective method for the synthesis of cocrystals, cocrystal polymorphs, and stoichiomorphs.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Multidisciplinary

Temperature-Controlled Mechanochemistry for the Nickel-Catalyzed Suzuki-Miyaura-Type Coupling of Aryl Sulfamates via Ball Milling and Twin-Screw Extrusion

Robert R. A. Bolt et al.

Summary: This article describes the use of temperature-controlled mechanochemistry for the mechanochemical nickel-catalyzed Suzuki-Miyaura coupling. The method eliminates the need for bulk solvents and is not affected by air/moisture, and has been successfully scaled up using twin-screw extrusion.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Multidisciplinary

Mechanocatalytic Room-Temperature Synthesis of Ammonia from Its Elements Down to Atmospheric Pressure

Steffen Reichle et al.

Summary: This study presents a new method for continuous ammonia production at room temperature and low pressure, achieving a breakthrough in the Haber-Bosch process. By optimizing experimental conditions, an efficient iron catalyst was successfully developed.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Taming Radical Pairs in the Crystalline Solid State: Discovery and Total Synthesis of Psychotriadine

Jordan J. Dotson et al.

Summary: Solid-state photodecarbonylation is used to assemble vicinal quaternary stereocenter motif in bis(cyclotryptamine) alkaloids. The success of the reaction is influenced by the substrate conformation, which was studied experimentally and computationally leading to the successful synthesis of psychotriadine, a previously unidentified compound found in extracts of Psychotria colorata.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Multidisciplinary Sciences

Mechanochemical synthesis of magnesium-based carbon nucleophiles in air and their use in organic synthesis

Rina Takahashi et al.

Summary: This study presents a method for the general mechanochemical synthesis of magnesium-based carbon nucleophiles in air using a ball milling technique, which avoids the drawbacks of using dry organic solvents and long reaction times.

NATURE COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides

Tamae Seo et al.

Summary: The study presents a fast and efficient solid-state method for Suzuki-Miyaura cross-coupling reactions that can handle reactions which are not feasible under traditional solution conditions. A new luminescent organic material with strong red emission was discovered and successfully prepared through molecular transformations.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

A Ball-Milling-Enabled Cross-Electrophile Coupling

Andrew C. Jones et al.

Summary: The nickel-catalyzed cross-electrophile coupling of aryl halides and alkyl halides enabled by ball-milling is efficient and green, achieving reductive C-C bond formation under a mechanochemical manifold. The mechanical action provided by ball milling allows for the use of a variety of zinc sources to turnover the nickel catalytic cycle, resulting in the synthesis of 28 cross-electrophile coupled products.

ORGANIC LETTERS (2021)

Article Multidisciplinary Sciences

Mechanochemical transformation of planar polyarenes to curved fused-ring systems

Teoh Yong et al.

Summary: The study demonstrates that mechanochemical forces can transform planar polyarenes into curved geometries by creating new C-C bonds, offering better yields and shorter reaction times without the need for inert conditions or organic solvents. This opens up a new reaction space for inducing curvature at a molecular level.

NATURE COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Beyond the Scholl reaction - one-step planarization and edge chlorination of nanographenes by mechanochemistry

Daniel M. Baier et al.

Summary: The edge chlorination of benchmark nanographenes is achieved through mechanochemical synthesis, which eliminates solubility limitations and the need for complex chlorination conditions. Furthermore, planarization of oligophenylenes and edge chlorination can be combined in a one-pot approach in as little as 60 minutes.

RSC ADVANCES (2021)

Article Chemistry, Multidisciplinary

Modular metal-free catalytic radical annulation of cyclic diaryliodoniums to access π-extended arenes

Daqian Zhu et al.

Summary: This study describes an alkylamine-mediated free radical intramolecular annulation to access PAHs under environmentally friendly conditions. By modulating substituents and their positions in the iodoniums, the free radical reaction controllably underwent three types of cyclization to form diverse PAHs frameworks. Preliminary mechanistic studies suggest that alkylamines initiated a radical pathway to efficiently complete the cyclization and further convert the products into complex graphene segments.

GREEN CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Mechanochemistry for Synthesis

Tomislav Friscic et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Multidisciplinary

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

Anthony Jolly et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Biochemistry & Molecular Biology

Continuous Flow Photochemistry for the Preparation of Bioactive Molecules

Mara Di Filippo et al.

MOLECULES (2020)

Article Chemistry, Multidisciplinary

Mechanochemical Cyclodehydrogenation with Elemental Copper: An Alternative Pathway toward Nanographenes

Sven Graetz et al.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2020)

Article Chemistry, Multidisciplinary

Mechanochemical Synthesis of Corannulene-Based Curved Nanographenes

Gabor Bati et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Investigations of Thermally Controlled Mechanochemical Milling Reactions

Nikola Cindro et al.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2019)

Article Chemistry, Multidisciplinary

Direct Mechanocatalysis: Palladium as Milling Media and Catalyst in the Mechanochemical Suzuki Polymerization

Christian G. Vogt et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

Precision synthesis versus bulk-scale fabrication of graphenes

Xiao-Ye Wang et al.

NATURE REVIEWS CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Toward Thiophene-Annulated Graphene Nanoribbons

Dandan Miao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Ball-free mechanochemistry: in situ real-time monitoring of pharmaceutical co-crystal formation by resonant acoustic mixing

Adam A. L. Michalchuk et al.

CHEMICAL COMMUNICATIONS (2018)

Article Chemistry, Multidisciplinary

The mechanochemical Scholl reaction - a solvent-free and versatile graphitization tool

Sven Graetz et al.

CHEMICAL COMMUNICATIONS (2018)

Review Chemistry, Organic

Organic Synthesis without Conventional Solvents

Martin Obst et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Solvent-free coupling of aryl halides with pyrroles applying visible-light photocatalysis

M. Obst et al.

REACTION CHEMISTRY & ENGINEERING (2017)

Article Chemistry, Multidisciplinary

Mechanochemical Synthesis of Phosphazane-Based Frameworks

Ying Sim et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Article Chemistry, Organic

Mechanochemical borylation of aryldiazonium salts; merging light and ball milling

Jose G. Hernandez

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Helically Coiled Graphene Nanoribbons

Maxime Daigle et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Regioselective Synthesis of Nanographenes by Photochemical Cyclodehydrochlorination

Maxime Daigle et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Organic

Solvent-free, visible-light photocatalytic alcohol oxidations applying an organic photocatalyst

Martin Obst et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Physical

Post-application of dry vortex grinding improves the yield of a [2+2] photodimerization: Addressing static disorder in a cocrystal

Elizabeth Elacqua et al.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

Large-Scale Green Chemical Synthesis of Adjacent Quaternary Chiral Centers by Continuous Flow Photodecarbonylation of Aqueous Suspensions of Nanocrystalline Ketones

Maria Guadalupe Hernandez-Linares et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

Synthesis of structurally well-defined and liquid-phase-processable graphene nanoribbons

Akimitsu Narita et al.

NATURE CHEMISTRY (2014)

Review Chemistry, Multidisciplinary

Mechanochemistry: opportunities for new and cleaner synthesis

Stuart L. James et al.

CHEMICAL SOCIETY REVIEWS (2012)

Article Chemistry, Multidisciplinary

Supramolecular Catalysis in the Organic Solid State through Dry Grinding

Anatoliy N. Sokolov et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Article Multidisciplinary Sciences

Atomically precise bottom-up fabrication of graphene nanoribbons

Jinming Cai et al.

NATURE (2010)

Article Chemistry, Organic

Controlling the Scholl reaction

Benjamin T. King et al.

JOURNAL OF ORGANIC CHEMISTRY (2007)