{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,21]],"date-time":"2026-02-21T00:11:04Z","timestamp":1771632664800,"version":"3.50.1"},"reference-count":323,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2021,12,27]],"date-time":"2021-12-27T00:00:00Z","timestamp":1640563200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004281","name":"National Science Center","doi-asserted-by":"publisher","award":["2019\/33\/B\/ST4\/00962"],"award-info":[{"award-number":["2019\/33\/B\/ST4\/00962"]}],"id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004281","name":"National Science Center","doi-asserted-by":"publisher","award":["2019\/35\/B\/ST4\/00115"],"award-info":[{"award-number":["2019\/35\/B\/ST4\/00115"]}],"id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004281","name":"National Science Center","doi-asserted-by":"publisher","award":["2019\/33\/N\/ST4\/00817"],"award-info":[{"award-number":["2019\/33\/N\/ST4\/00817"]}],"id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004281","name":"National Science Center","doi-asserted-by":"publisher","award":["2021\/05\/X\/ST4\/00393"],"award-info":[{"award-number":["2021\/05\/X\/ST4\/00393"]}],"id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Materials"],"abstract":"<jats:p>Phenyl, naphthyl, polyarylphenyl, coronene, and other aromatic and polyaromatic moieties primarily influence the final materials\u2019 properties. One of the synthetic tools used to implement (hetero)aromatic moieties into final structures is Diels\u2013Alder 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.<\/jats:p>","DOI":"10.3390\/ma15010172","type":"journal-article","created":{"date-parts":[[2021,12,28]],"date-time":"2021-12-28T01:20:43Z","timestamp":1640654443000},"page":"172","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Diels\u2013Alder Cycloaddition with CO, CO2, SO2, or N2 Extrusion: A Powerful Tool for Material Chemistry"],"prefix":"10.3390","volume":"15","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3516-4235","authenticated-orcid":false,"given":"Stanis\u0142aw","family":"Krompiec","sequence":"first","affiliation":[{"name":"Institute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6004-3000","authenticated-orcid":false,"given":"Aneta","family":"Kurpanik-W\u00f3jcik","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3108-4182","authenticated-orcid":false,"given":"Marek","family":"Matussek","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5763-9089","authenticated-orcid":false,"given":"Bogumi\u0142a","family":"Go\u0142ek","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5911-4254","authenticated-orcid":false,"given":"Angelika","family":"Mieszczanin","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8012-3910","authenticated-orcid":false,"given":"Aleksandra","family":"Fijo\u0142ek","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,12,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"5082","DOI":"10.1002\/anie.201701054","article-title":"Unsymmetric Twofold Scholl Cyclization of a 5,11-Dinaphthyltetracene: Selective Formation of Pentagonal and Hexagonal Rings via Dicationic Intermediates","volume":"56","author":"Murata","year":"2017","journal-title":"Angew. 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