Diels–Alder Cycloaddition to the Bay Region of Perylene and Its Derivatives as an Attractive Strategy for PAH Core Expansion: Theoretical and Practical Aspects

PAHs (polycyclic aromatics hydrocarbons), the compound group that contains perylene and its derivatives, including functionalized ones, have attracted a great deal of interest in many fields of science and modern technology. This review presents all of the research devoted to modifications of PAHs t...

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Published inMolecules (Basel, Switzerland) Vol. 25; no. 22; p. 5373
Main Authors Kurpanik, Aneta, Matussek, Marek, Lodowski, Piotr, Szafraniec-Gorol, Grażyna, Krompiec, Michał, Krompiec, Stanisław
Format Journal Article
LanguageEnglish
Published Switzerland MDPI 17.11.2020
MDPI AG
Subjects
APEX
bay region
Cycloaddition Reaction
Diels–Alder cycloaddition
Esters - chemistry
nanographenes
perylene
Perylene - chemistry
Polycyclic Aromatic Hydrocarbons - chemistry
Review
Thermodynamics
perylene
Diels–Alder cycloaddition
bay region
APEX
nanographenes
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Abstract PAHs (polycyclic aromatics hydrocarbons), the compound group that contains perylene and its derivatives, including functionalized ones, have attracted a great deal of interest in many fields of science and modern technology. This review presents all of the research devoted to modifications of PAHs that are realized via the Diels–Alder (DA) cycloaddition of various dienophiles to the bay regions of PAHs, leading to the π-extension of the starting molecule. This type of annulative π-extension (APEX) strategy has emerged as a powerful and efficient synthetic method for the construction of polycyclic aromatic hydrocarbons and their functionalized derivatives, nanographenes, and π-extended fused heteroarenes. Then, [4 + 2] cycloadditions of ethylenic dienophiles, -N=N-, i.e., diazo-dienophiles and acetylenic dienophiles, are presented. This subject is discussed from the organic synthesis point of view but supported by theoretical calculations. The possible applications of DA cycloaddition to PAH bay regions in various science and technology areas, and the prospects for the development of this synthetic method, are also discussed.
AbstractList PAHs (polycyclic aromatics hydrocarbons), the compound group that contains perylene and its derivatives, including functionalized ones, have attracted a great deal of interest in many fields of science and modern technology. This review presents all of the research devoted to modifications of PAHs that are realized via the Diels-Alder (DA) cycloaddition of various dienophiles to the bay regions of PAHs, leading to the π-extension of the starting molecule. This type of annulative π-extension (APEX) strategy has emerged as a powerful and efficient synthetic method for the construction of polycyclic aromatic hydrocarbons and their functionalized derivatives, nanographenes, and π-extended fused heteroarenes. Then, [4 + 2] cycloadditions of ethylenic dienophiles, -N=N-, i.e., diazo-dienophiles and acetylenic dienophiles, are presented. This subject is discussed from the organic synthesis point of view but supported by theoretical calculations. The possible applications of DA cycloaddition to PAH bay regions in various science and technology areas, and the prospects for the development of this synthetic method, are also discussed.PAHs (polycyclic aromatics hydrocarbons), the compound group that contains perylene and its derivatives, including functionalized ones, have attracted a great deal of interest in many fields of science and modern technology. This review presents all of the research devoted to modifications of PAHs that are realized via the Diels-Alder (DA) cycloaddition of various dienophiles to the bay regions of PAHs, leading to the π-extension of the starting molecule. This type of annulative π-extension (APEX) strategy has emerged as a powerful and efficient synthetic method for the construction of polycyclic aromatic hydrocarbons and their functionalized derivatives, nanographenes, and π-extended fused heteroarenes. Then, [4 + 2] cycloadditions of ethylenic dienophiles, -N=N-, i.e., diazo-dienophiles and acetylenic dienophiles, are presented. This subject is discussed from the organic synthesis point of view but supported by theoretical calculations. The possible applications of DA cycloaddition to PAH bay regions in various science and technology areas, and the prospects for the development of this synthetic method, are also discussed.
PAHs (polycyclic aromatics hydrocarbons), the compound group that contains perylene and its derivatives, including functionalized ones, have attracted a great deal of interest in many fields of science and modern technology. This review presents all of the research devoted to modifications of PAHs that are realized via the Diels–Alder (DA) cycloaddition of various dienophiles to the bay regions of PAHs, leading to the π-extension of the starting molecule. This type of annulative π-extension (APEX) strategy has emerged as a powerful and efficient synthetic method for the construction of polycyclic aromatic hydrocarbons and their functionalized derivatives, nanographenes, and π-extended fused heteroarenes. Then, [4 + 2] cycloadditions of ethylenic dienophiles, -N=N-, i.e., diazo-dienophiles and acetylenic dienophiles, are presented. This subject is discussed from the organic synthesis point of view but supported by theoretical calculations. The possible applications of DA cycloaddition to PAH bay regions in various science and technology areas, and the prospects for the development of this synthetic method, are also discussed.
Author Krompiec, Michał
Matussek, Marek
Kurpanik, Aneta
Lodowski, Piotr
Szafraniec-Gorol, Grażyna
Krompiec, Stanisław
AuthorAffiliation 1 Institute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, Poland; aneta.kurpanik@gmail.com (A.K.); matussekmarek@gmail.com (M.M.); piotr.lodowski@us.edu.pl (P.L.); grazyna.szafraniec-gorol@us.edu.pl (G.S.-G.)
3 School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
2 Merck Chemicals Ltd., 1 Venture Road, Southampton SO16 7NP, UK; michal.krompiec@gmail.com
AuthorAffiliation_xml – name: 2 Merck Chemicals Ltd., 1 Venture Road, Southampton SO16 7NP, UK; michal.krompiec@gmail.com
– name: 3 School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
– name: 1 Institute of Chemistry, Faculty of Science and Technology, University of Silesia, Bankowa 14, 40-007 Katowice, Poland; aneta.kurpanik@gmail.com (A.K.); matussekmarek@gmail.com (M.M.); piotr.lodowski@us.edu.pl (P.L.); grazyna.szafraniec-gorol@us.edu.pl (G.S.-G.)
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Issue 22
Keywords perylene
Diels–Alder cycloaddition
bay region
APEX
nanographenes
Language English
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Snippet PAHs (polycyclic aromatics hydrocarbons), the compound group that contains perylene and its derivatives, including functionalized ones, have attracted a great...
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SubjectTerms APEX
bay region
Cycloaddition Reaction
Diels–Alder cycloaddition
Esters - chemistry
nanographenes
perylene
Perylene - chemistry
Polycyclic Aromatic Hydrocarbons - chemistry
Review
Thermodynamics
Title Diels–Alder Cycloaddition to the Bay Region of Perylene and Its Derivatives as an Attractive Strategy for PAH Core Expansion: Theoretical and Practical Aspects
URI https://www.ncbi.nlm.nih.gov/pubmed/33213037
https://www.proquest.com/docview/2463102843
https://pubmed.ncbi.nlm.nih.gov/PMC7698498
https://doaj.org/article/b06632a126a6450d90e0c2eaa841dae6
Volume 25
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