Microwave‐Assisted Facile Synthesis and Crystal Structure of <i>cis</i>‐9,10,11,15‐Tetrahydro‐9,10[3′,4′]‐furanoanthracene‐12,14‐dione

Phutdhawong, Weerachai; Buddhasukh, Duang; Pyne, Stephen G.; Rujiwatra, Apinpus; Pakawatchai, Chaveng

doi:10.1080/00397910500466025

Cited by 7 publications

(3 citation statements)

References 3 publications

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“…This suggests that α is due to MAH somehow taken up into the crystal, while β is due to the expected MAH DA adduct. This latter assignment was confirmed by model studies (for details, see Supporting Information, section S1e) and is in line with reported shifts of such DA adducts . Why and how MAH is taken up into the crystals is not yet understood.…”

Section: Resultssupporting

confidence: 81%

Decorating the Edges of a 2D Polymer with a Fluorescence Label

et al. 2016

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This work proves the existence and chemical addressability of defined edge groups of a 2D polymer. Pseudohexagonally prismatic single crystals consisting of layered stacks of a 2D polymer are used. They should expose anthracene-based edge groups at the six (100) but not at the two pseudohexagonal (001) and (001̅) faces. The crystals are reacted with the isotopically enriched dienophiles maleic anhydride and a C18-alkyl chain-modified maleimide. In both cases the corresponding Diels-Alder adducts between these reagents and the edge groups are formed as confirmed by solid state NMR spectroscopy. The same applies to a maleimide derivative carrying a BODIPY dye which was chosen for its fluorescence to be out of the range of the self-fluorescence of the 2D polymer crystals stemming from contained template molecules. If the crystals are excited at λ = 633 nm, their (100) faces and thus their rims fluoresce brightly, while the pseudohexagonal faces remain silent. This is visible when the crystals lie on a pseudohexagonal face. Lambda-mode laser scanning microscopy confirms this fluorescence to originate from the BODIPY dye. Micromechanical exfoliation of the dye-modified crystals results in thinner sheet packages which still exhibit BODIPY fluorescence right at the rim of these packages. This work establishes the chemical nature of the edge groups of a 2D polymer and is also the first implementation of an edge group modification similar to end group modifications of linear polymers.

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Section: Resultssupporting

confidence: 81%

Decorating the Edges of a 2D Polymer with a Fluorescence Label

et al. 2016

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“…Pericyclic reactions such as the Diels–Alder and hetero-Diels–Alder cycloadditions, the Alder-En reaction, as well as the decarboxylation of α-alkylated malonic acids, are also suitable for flow protocols in combination with inductive heating ( Scheme 10 , case A) [ 53 ]. The yields but especially the residence times of the reactions outperformed those of the analogous experiments carried out under batch conditions by far [ 62 – 64 ].…”

Section: Reviewmentioning

confidence: 99%

Inductive heating and flow chemistry – a perfect synergy of emerging enabling technologies

Kuhwald¹,

Türkhan²,

Kirschning³

2022

Beilstein J. Org. Chem.

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Inductive heating has developed into a powerful and rapid indirect heating technique used in various fields of chemistry, but also in medicine. Traditionally, inductive heating is used in industry, e.g., for heating large metallic objects including bending, bonding, and welding pipes. In addition, inductive heating has emerged as a partner for flow chemistry, both of which are enabling technologies for organic synthesis. This report reviews the combination of flow chemistry and inductive heating in industrial settings as well as academic research and demonstrates that the two technologies ideally complement each other.

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“…[5] In this communication, we report a novel method for the synthesis of N,N 0 -disubstituted acetamidines using a modified domestic microwave oven. [6,7] Scheme 1. Synthesis of acetamidine.…”

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confidence: 99%