{
  "abstract": "In this work, we demonstrate that poly(ethylene glycol)-400 (PEG-400) can efficiently replace conventional and hazardous solvents such as N,N-dimethylaminoethanol (DMAE) and N,N-dimethylformamide (DMF) in the synthesis of phthalocyanines, a class of functional molecular materials widely investigated for optoelectronic and energy-related applications. Used at a loading as low as 1.0 equivalent relative to the phthalonitrile precursor, PEG-400 enables cyclotetramerization reactions under operationally simple and comparatively safer conditions, providing isolated yields of 50-83% across a range of metalated and metal-free derivatives and substitution patterns. The robustness of the protocol was further demonstrated at the multigram scale, affording cobalt phthalocyanine in 79% yield, with 88% of the PEG-400 recovered from the reaction mixture. Remarkably, PEG-400 proved compatible with sequential cyclotetramerization followed by Sonogashira or Suzuki coupling without isolation of the macrocyclic intermediate, affording functionalized products in up to 75% yield and enabling pot-economical access to more complex derivatives. E-factor and Process Mass Intensity (PMI) analyses quantitatively support the improved material-efficiency profile of the method when compared to representative literature procedures. Overall, these results establish PEG-400 as a versatile and sustainable medium for the resource-efficient synthesis and functionalization of phthalocyanine derivatives.",
  "abstract_shown": true,
  "affiliations": [
    "Istituto di Struttura della Materia (CNR-ISM), Strada provinciale 35d/9, Montelibretti, Italy, 00010",
    "Department of Chemistry, Sapienza University of Rome, P.le Aldo Moro 5, Rome, Italy, 00185",
    "Istituto di Struttura della Materia (CNR-ISM), Via del Fosso del Cavaliere 100, Rome, Italy, 00133",
    "Department of Chemistry and Technology of Drugs, Sapienza University of Rome, P.le Aldo Moro 5, Rome, Italy, 00185"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 5,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Federica Palmeri",
      "orcid": "0009-0002-8731-0724"
    },
    {
      "affs": [
        2
      ],
      "name": "Venanzio Raglione",
      "orcid": "0000-0003-3334-5171"
    },
    {
      "affs": [
        3
      ],
      "name": "Chiara Salvitti",
      "orcid": "0000-0002-9184-1299"
    },
    {
      "affs": [
        3
      ],
      "name": "Anna Troiani",
      "orcid": "0000-0002-6412-9407"
    },
    {
      "affs": [
        0
      ],
      "name": "Gloria Zanotti",
      "orcid": "0000-0002-1568-3591"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/3vpcmzj596y35.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15007374/v2",
  "fulltext_url": null,
  "id": "3vpcmzj596y35",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15007374/v2",
  "language": null,
  "licence": "CC-BY-NC-ND",
  "licence_label": "CC BY-NC-ND",
  "licence_source": "journal",
  "licence_url": "https://creativecommons.org/licenses/by-nc-nd/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "2505|Porphyrin and Phthalocyanine Chemistry"
    ]
  ],
  "openalex": "W7213275716",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15007374/v2",
  "pmcid": null,
  "pmid": null,
  "published": "2026-09-16",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/3vpcmzj596y35.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:19Z",
      "native_id": "10.26434/chemrxiv.15007374",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15007374/v2"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:2505|Porphyrin and Phthalocyanine Chemistry",
      "subfield": "materials-polymers"
    }
  ],
  "title": "Unlocking PEG-400: A Sustainable Reaction Medium for Phthalocyanine Synthesis and Pd-Catalyzed C–C Bond Formation",
  "title_text": "Unlocking PEG-400: A Sustainable Reaction Medium for Phthalocyanine Synthesis and Pd-Catalyzed C–C Bond Formation",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:19Z",
  "url": "https://research.draconitic.com/paper/3vpcmzj596y35",
  "venue": "ChemRxiv",
  "versions": []
}