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首页> 外文期刊>Chemistry: A European journal >Intramolecular domino electrophilic and thermal cyclization of peri-ethynylene naphthalene oligomers
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Intramolecular domino electrophilic and thermal cyclization of peri-ethynylene naphthalene oligomers

机译：亚乙炔基萘低聚物的分子内多米诺亲电和热环化

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摘要

The intramolecular electrophilic or thermal cyclization of arylene ethynylene precursors recently became a powerful method for the synthesis of new polycyclic aromatic hydrocarbons (PAHs). In this work, we investigated in detail the synthesis and intramolecular cyclization reaction of a series of peri-ethynylene naphthalene oligomers in which the ethynylene units are fixed in close proximity within the naphthalene framework. The high reactivity of these precursors led to simultaneous thermal cyclization reactions, even during their syntheses. Electrophilic cyclizations with iodine were also undertaken. Several new PAHs containing five-membered rings, for example, indeno[2,1-a]phenalene, acenaphtho[1,2-a]pyrene, and benzo- or naphtho-annulated fluoranthene derivatives, were synthesized and their structures were unambiguously determined by X-ray crystallographic analysis. Plausible mechanisms were proposed and it was demonstrated that oligomers most probably underwent intramolecular domino cyclization via either radical or cationic intermediates. The photophysical and electrochemical properties of these new PAHs were investigated and some of them displayed amphoteric redox behavior, due to the existence of five-membered rings.
机译：亚芳基亚乙炔基前体的分子内亲电或热环化最近成为合成新型多环芳烃（PAHs）的有力方法。在这项工作中，我们详细研究了一系列亚乙炔基萘低聚物的合成和分子内环化反应，其中亚乙炔基单元紧密固定在萘骨架内。这些前体的高反应性导致了同时的热环化反应，即使在合成过程中也是如此。还进行了碘的亲电环化。合成了几种新的含五元环的PAH，例如茚并[2,1-a]苯、, [1,2-a] py和苯并-或萘并环的荧蒽衍生物，并明确确定了它们的结构通过X射线晶体学分析。提出了合理的机制，并证明低聚物最有可能通过自由基或阳离子中间体经历了分子内多米诺环化反应。研究了这些新的PAHs的光物理和电化学性质，由于五元环的存在，其中一些具有两性氧化还原行为。

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