{
  "abstract": "Silicon-substituted polycyclic aromatic hydrocarbons (Si-PAHs) are important functional π-conjugated molecules, but their synthesis is still largely dependent on the multistep preparation of precursors, such as halogenated PAHs. Herein, we report a lithium-mediated mechanochemical Birch reductive silylation of unfunctionalized PAHs in air at room temperature. Various silylated PAHs (Si-PAHs) and hydrogenated analogues were obtained directly from unfunctionalized PAHs by ball-milling PAHs with bulk Li(0) in a small amount of THF additive, followed by treatment with chlorosilanes, fluorosilanes, or hydrosilanes. This method accommodates a range of PAHs, including chrysene, fluoranthene, and perylene derivatives, and enables access to various substitution patterns that are difficult to achieve using conventional synthetic methods. The resulting Si-PAHs exhibit enhanced solubility and fluorescent quantum yields, along with a characteristic red shift in absorption and emission. Furthermore, the combination of the previously developed Li(0)-mediated mechanochemical cyclodehydrogenation and Birch reductive arylation with the present silylation enabled one-pot access to more complicated functional Si-PAHs.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry, Graduate School of Science, Nagoya University Chikusa Nagoya 464-8602 Japan"
  ],
  "article_type": "research article",
  "arxiv": null,
  "author_total": 3,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Shota Mikawa",
      "orcid": "0009-0002-1554-2884"
    },
    {
      "affs": [
        0
      ],
      "name": "Yoshifumi Toyama",
      "orcid": "0009-0002-1324-0946"
    },
    {
      "affs": [
        0
      ],
      "name": "Hideto Ito",
      "orcid": "0000-0002-4034-6247"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/69mexhg0w3pvr.bib",
  "cited_by": 1,
  "doi": "10.1039/d6sc05649k",
  "fulltext_url": "https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13725590/?tool=EBI",
  "id": "69mexhg0w3pvr",
  "issns": [
    "2041-6520",
    "2041-6539"
  ],
  "landing_url": "https://europepmc.org/article/PMC/PMC13725590",
  "language": "eng",
  "licence": "CC-BY-NC",
  "licence_label": "CC BY-NC",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by-nc/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "heading",
      "Chemistry"
    ],
    [
      "openalex",
      "1605|Organoboron and organosilicon chemistry"
    ]
  ],
  "openalex": "W7162397585",
  "pdf_url": "https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13725590/pdf/?tool=EBI",
  "pmcid": "PMC13725590",
  "pmid": "42974230",
  "published": "2026-11-02",
  "publisher": "Royal Society of Chemistry",
  "ris": "https://research.draconitic.com/paper/69mexhg0w3pvr.ris",
  "sources": [
    {
      "first_seen": "2026-11-03T15:20:50Z",
      "native_id": "PMC:PMC13725590",
      "source": "europepmc",
      "url": "https://europepmc.org/article/PMC/PMC13725590"
    },
    {
      "first_seen": "2026-11-04T12:23:56Z",
      "native_id": "PMC13725590",
      "source": "pmc",
      "url": "https://doi.org/10.1039/d6sc05649k"
    },
    {
      "first_seen": "2026-11-04T15:20:47Z",
      "native_id": "MED:42974230",
      "source": "europepmc",
      "url": "https://europepmc.org/article/MED/42974230"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Organoboron and organosilicon chemistry",
      "subfield": "organic"
    }
  ],
  "title": "Synthesis of silylated polycyclic aromatic hydrocarbons by lithium-mediated mechanochemical Birch reductive silylation† † Dedicated to the memory of Dr Kazuhiko Sato at the National Institute of Advanced Industrial Science and Technology (AIST), Japan, in recognition of his outstanding contributions to silicon chemistry and catalysis, and in mourning of his untimely passing.",
  "title_text": "Synthesis of silylated polycyclic aromatic hydrocarbons by lithium-mediated mechanochemical Birch reductive silylation† † Dedicated to the memory of Dr Kazuhiko Sato at the National Institute of Advanced Industrial Science and Technology (AIST), Japan, in recognition of his outstanding contributions to silicon chemistry and catalysis, and in mourning of his untimely passing.",
  "type": "peer-reviewed",
  "updated_at": "2026-11-06T12:21:47Z",
  "url": "https://research.draconitic.com/paper/69mexhg0w3pvr",
  "venue": "Chemical science",
  "versions": []
}