{
  "abstract": "How local molecular determinants encode stability and dynamics in supramolecular assemblies remains a central challenge in adapting biological design principles for synthetic systems. Here, we systematically investigate eleven amino acid-functionalized benzene-1,3,5-tricarboxamides to elucidate how chirality, α-substitution, and side-chain architecture control the formation, stability and function of noncovalent octameric capsules. Achiral derivatives lacking an α-hydrogen exhibit poor solubility in noncompetitive solvents and preferentially form extended polymeric aggregates, highlighting the role of the α-H motif in mediating solvation and preorganization of hydrogen-bonding networks. In contrast, chiral analogues retaining the α-H group readily self-assemble into discrete, D2-symmetric octameric capsules. Substitution of the α-hydrogen with a methyl group disrupts solubility and capsular stability; however, introduction of long aliphatic side chains partially restores capsule formation, albeit with increased dynamics. Moreover, α-methylation profoundly affects capsule function, leading to a complete loss of fullerene encapsulation ability compared to the corresponding α-H-containing capsules. Overall, these results reveal how subtle variations at the α-position translate into emergent differences in stability, dynamics, function and architecture of hydrogen-bonded supramolecular capsules.",
  "abstract_shown": true,
  "affiliations": [
    "Center for Advanced Technologies, Adam Mickiewicz University Uniwersytetu Poznańskiego 10 61-614 Poznań Poland ars@amu.edu.pl.",
    "Faculty of Chemistry, Adam Mickiewicz University Uniwersytetu Poznańskiego 8 61-614 Poznań Poland.",
    "Department of Chemistry, Molecular Sciences Research Hub, Imperial College London 82 Wood Lane London W12 0BZ UK.",
    "Department of Chemistry, University College London Christopher Ingold Building 20 Gordon St London WC1H 0AJ UK."
  ],
  "article_type": "research article",
  "arxiv": null,
  "author_total": 6,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Filip Perlitius",
      "orcid": "0000-0003-0423-849X"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Grzegorz Markiewicz",
      "orcid": "0000-0003-0605-3210"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Mateusz Gołdyn",
      "orcid": "0000-0003-2282-9816"
    },
    {
      "affs": [
        2,
        3
      ],
      "name": "Gokay Avci"
    },
    {
      "affs": [
        2
      ],
      "name": "Kim E Jelfs",
      "orcid": "0000-0001-7683-7630"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Artur R Stefankiewicz",
      "orcid": "0000-0002-6177-358X"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/5psekgwesakpd.bib",
  "cited_by": 0,
  "doi": "10.1039/d6qo01259k",
  "fulltext_url": "https://europepmc.org/articles/PMC13742164",
  "id": "5psekgwesakpd",
  "issns": [
    "2052-4110",
    "2052-4129"
  ],
  "landing_url": "https://europepmc.org/article/MED/42997531",
  "language": "eng",
  "licence": "CC-BY",
  "licence_label": "CC BY",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Supramolecular Chemistry and Complexes"
    ]
  ],
  "openalex": "W7225400998",
  "pdf_url": "https://pubs.rsc.org/qo/article-pdf/doi/10.1039/d6qo01259k/15055364/d6qo01259k.pdf",
  "pmcid": "PMC13742164",
  "pmid": "42997531",
  "published": "2026-11-06",
  "publisher": null,
  "ris": "https://research.draconitic.com/paper/5psekgwesakpd.ris",
  "sources": [
    {
      "first_seen": "2026-11-09T15:20:34Z",
      "native_id": "MED:42997531",
      "source": "europepmc",
      "url": "https://europepmc.org/article/MED/42997531"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Supramolecular Chemistry and Complexes",
      "subfield": "organic"
    }
  ],
  "title": "Encoding stability and dynamics in hydrogen-bonded octameric capsules through amino acid α-position design.",
  "title_text": "Encoding stability and dynamics in hydrogen-bonded octameric capsules through amino acid α-position design.",
  "type": "peer-reviewed",
  "updated_at": "2026-11-09T15:20:34Z",
  "url": "https://research.draconitic.com/paper/5psekgwesakpd",
  "venue": "Organic chemistry frontiers : an international journal of organic chemistry",
  "versions": []
}