{"title":"AzUlene-Fused Polycyclic Aromatic Hydrocarbons: Synthesis, Structural, Optical, and Electrochemical Properties of Azuleno[2,1-a]phenalenones","authors":"Taku Shoji, Naoko Sakata, Ryunosuke Ishikawa, Shigeki Mori, Tetsuo Okujima, Ryuta Sekiguchi, Shunji Ito","doi":"10.1002/ceur.202500039","DOIUrl":null,"url":null,"abstract":"<p>The preparation of 2-arylazulenes possessing 1-naphthyl substructure is achieved via Suzuki–Miyaura coupling with various arylboronic acids. Intramolecular cyclization using Brønsted acids is examined, yielding azulene-fused polycyclic aromatic hydrocarbons, that is, azuleno[2,1-<i>a</i>]phenalenones, in high yields. The optical properties of azuleno[2,1-<i>a</i>]phenalenones are characterized by UV/vis and fluorescence spectroscopy, revealing halochromic behavior and significant fluorescence under acidic conditions. Electrochemical properties are also assessed using voltammetry and spectroelectrochemical experiments, identifying compounds with remarkable electrochromic behavior.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 3","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202500039","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemistryEurope","FirstCategoryId":"1085","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/ceur.202500039","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
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Abstract
The preparation of 2-arylazulenes possessing 1-naphthyl substructure is achieved via Suzuki–Miyaura coupling with various arylboronic acids. Intramolecular cyclization using Brønsted acids is examined, yielding azulene-fused polycyclic aromatic hydrocarbons, that is, azuleno[2,1-a]phenalenones, in high yields. The optical properties of azuleno[2,1-a]phenalenones are characterized by UV/vis and fluorescence spectroscopy, revealing halochromic behavior and significant fluorescence under acidic conditions. Electrochemical properties are also assessed using voltammetry and spectroelectrochemical experiments, identifying compounds with remarkable electrochromic behavior.
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