{
  "abstract": "This study develops a one-pot synthetic system that concurrently produces two classes of functional materials via a previously unobserved transformation of perfluorotoluene under nucleophilic conditions. Building on prior work with fluorinated discotic systems, the reaction of 2,2'-dilithio-1,1'-biaryls with perfluorotoluene (C₆F₅-CF₃) furnishes trifluoromethylated trifluorotriphenylene derivatives (TPFn, n = 1-4, 6, 8, 10, 8/2) alongside structurally distinct dearomatized spirofluorene analogues (TPFn-1). The formation of the spirofluorene compounds points to a competing pathway beyond classical aryl nucleophilic substitution. Based on structural evidences, a de-aromatization process involving cleavage of four C-F bonds (one from the pentafluorophenyl ring and three from the CF₃ group) and subsequent formation of new C-C bonds is proposed to account for the formation of the spiro-fused architecture. This side reaction sheds light on the moderate yields of the target TPFn series and highlights the complex reactivity of perfluorotoluene with 2,2'-dilithio-1,1'-biaryls. All TPFn compounds form thermally stable hexagonal columnar (Colhex) mesophases with large liquid-crystalline ranges, along with a strong modulation of the clearing temperatures with alkoxy chain-lengths. Despite the presence of the bulky lateral CF3 group, the transition temperatures are surprisingly not greatly affected when compared to previously synthesized 4F-TPn homologous compounds (with no CF3 groups). Structural analysis, supported by X-ray crystallography of di-tert-butyl model compound (tBuTPF), validates the molecular design and packing. This work thus provides a practical one-pot route to potentially fluorinated discotic semiconductors while revealing a competing transformation that advances the understanding of polyfluorinated arene chemistry and offers access to novel spiro-fused molecular architectures.",
  "abstract_shown": true,
  "affiliations": [],
  "article_type": null,
  "arxiv": null,
  "author_total": 7,
  "authors": [
    {
      "name": "Jiao Jian"
    },
    {
      "name": "Ming-Mei Zhou"
    },
    {
      "name": "Wen-Hao Yu"
    },
    {
      "name": "Xiao-Yan Bai"
    },
    {
      "name": "Ke-Xiao Zhao"
    },
    {
      "name": "Ke-Qing Zhao"
    },
    {
      "name": "Bertrand Donnio"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/4zghv6pebgd4b.bib",
  "cited_by": 1,
  "doi": "10.1021/acs.joc.6c00735",
  "fulltext_url": null,
  "id": "4zghv6pebgd4b",
  "issns": [
    "0022-3263",
    "1520-6904"
  ],
  "landing_url": "https://hal.science/hal-05807227v1",
  "language": "en",
  "licence": "CC-BY-NC-ND-4.0",
  "licence_label": "CC BY-NC-ND 4.0",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by-nc-nd/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "hal",
      "0.chim"
    ],
    [
      "hal",
      "1.chim.cris"
    ],
    [
      "hal",
      "1.chim.mate"
    ],
    [
      "hal",
      "1.chim.orga"
    ],
    [
      "openalex",
      "2504|Liquid Crystal Research Advancements"
    ]
  ],
  "openalex": "W7166563368",
  "pdf_url": "https://hal.science/hal-05807227/document",
  "pmcid": null,
  "pmid": null,
  "published": "2026-06-29",
  "publisher": "American Chemical Society",
  "ris": "https://research.draconitic.com/paper/4zghv6pebgd4b.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:59Z",
      "native_id": "hal-05807227",
      "source": "hal",
      "url": "https://hal.science/hal-05807227v1"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "hal:1.chim.cris",
      "subfield": "inorganic"
    },
    {
      "field": "chemistry",
      "origin": "hal:1.chim.mate",
      "subfield": "materials-polymers"
    },
    {
      "field": "chemistry",
      "origin": "hal:1.chim.orga",
      "subfield": "organic"
    }
  ],
  "title": "From Targeted Synthesis to Serendipitous Discovery: Transforming Perfluorotoluene into Discotic Liquid Crystals and Dearomatized Spirofluorenes",
  "title_text": "From Targeted Synthesis to Serendipitous Discovery: Transforming Perfluorotoluene into Discotic Liquid Crystals and Dearomatized Spirofluorenes",
  "type": "peer-reviewed",
  "updated_at": "2026-10-30T12:17:59Z",
  "url": "https://research.draconitic.com/paper/4zghv6pebgd4b",
  "venue": "Journal of Organic Chemistry",
  "versions": []
}