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Title: Diels-Alder cycloaddition with CO, CO2, SO2, or N2 extrusion : a powerful tool for material chemistry
Authors: Krompiec, Stanisław
Kurpanik-Wójcik, Aneta
Matussek, Marek
Gołęk, Bogumiła
Mieszczanin, Angelika
Fijołek, Aleksandra
Keywords: Diels–Alder cycloaddition; extrusion; APEX strategy; functionalized nanomaterials; nanographenes; organic electronics; polycyclic aromatic hydrocarbons; polyarenes
Issue Date: 2022
Citation: "Materials" (2022), iss. 1, art. no 172, s. 1-149
Abstract: Phenyl, naphthyl, polyarylphenyl, coronene, and other aromatic and polyaromatic moieties primarily influence the final materials’ properties. One of the synthetic tools used to implement (hetero) aromatic moieties into final structures is Diels–Alder cycloaddition (DAC), typically combined with Scholl dehydrocondensation. Substituted 2-pyranones, 1,1-dioxothiophenes, and, especially, 1,3-cyclopentadienones are valuable substrates for [4 + 2] cycloaddition, leading to multisubstituted derivatives of benzene, naphthalene, and other aromatics. Cycloadditions of dienes can be carried out with extrusion of carbon dioxide, carbon oxide, or sulphur dioxide. When pyranones, dioxothiophenes, or cyclopentadienones and DA cycloaddition are aided with acetylenes including masked ones, conjugated or isolated diynes, or polyynes and arynes, aromatic systems are obtained. This review covers the development and the current state of knowledge regarding thermal DA cycloaddition of dienes mentioned above and dienophiles leading to (hetero)aromatics via CO, CO2, or SO2 extrusion. Particular attention was paid to the role that introduced aromatic moieties play in designing molecular structures with expected properties. Undoubtedly, the DAC variants described in this review, combined with other modern synthetic tools, constitute a convenient and efficient way of obtaining functionalized nanomaterials, continually showing the potential to impact materials sciences and new technologies in the nearest future.
DOI: 10.3390/ma15010172
ISSN: 1996-1944
Appears in Collections:Artykuły (WNŚiT)

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