{"title":"Synthesis and Properties of Cross-Shaped Polycyclic Aromatic Hydrocarbons","authors":"Junkai Huang, Lingyun Zhu, Taosong Wang, Ruiying Zhang, Yanxia Huang, Zi'ang Zhai, Yaohuan Mei, Lili Xie, Yuanming Li","doi":"10.1002/hlca.202500075","DOIUrl":null,"url":null,"abstract":"<p>The synthesis and characterization of cross-shaped π-extended dibenzo[<i>e,l</i>]pyrene derivatives with combined fjord and armchair edge structures were reported. The target molecules were synthesized via Yamamoto coupling and Scholl reactions, and their structures were fully characterized by nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HR-MS), and single-crystal X-ray diffraction. Photophysical studies revealed a significant redshift in absorption and emission spectra compared to the parent dibenzo[<i>e,l</i>]pyrene, attributed to the extended π-conjugation system. Density functional theory (DFT) calculations provided insights into the molecular orbital distribution and reduced bandgap resulting from the elongated conjugation pathway. This work offers a versatile synthetic strategy for polycyclic aromatic hydrocarbons with tailored edge topologies and paves the way for their potential applications in optoelectronic materials.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"108 8","pages":""},"PeriodicalIF":1.8000,"publicationDate":"2025-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Helvetica Chimica Acta","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/hlca.202500075","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
The synthesis and characterization of cross-shaped π-extended dibenzo[e,l]pyrene derivatives with combined fjord and armchair edge structures were reported. The target molecules were synthesized via Yamamoto coupling and Scholl reactions, and their structures were fully characterized by nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HR-MS), and single-crystal X-ray diffraction. Photophysical studies revealed a significant redshift in absorption and emission spectra compared to the parent dibenzo[e,l]pyrene, attributed to the extended π-conjugation system. Density functional theory (DFT) calculations provided insights into the molecular orbital distribution and reduced bandgap resulting from the elongated conjugation pathway. This work offers a versatile synthetic strategy for polycyclic aromatic hydrocarbons with tailored edge topologies and paves the way for their potential applications in optoelectronic materials.
期刊介绍：
Helvetica Chimica Acta, founded by the Swiss Chemical Society in 1917, is a monthly multidisciplinary journal dedicated to the dissemination of knowledge in all disciplines of chemistry (organic, inorganic, physical, technical, theoretical and analytical chemistry) as well as research at the interface with other sciences, where molecular aspects are key to the findings. Helvetica Chimica Acta is committed to the publication of original, high quality papers at the frontier of scientific research. All contributions will be peer reviewed with the highest possible standards and published within 3 months of receipt, with no restriction on the length of the papers and in full color.
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