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Peer-reviewedCC BY 4.0ACS Omega

Introducing Chirality into Graphene Oxide Layers through a Facile Amino Acid-Based Covalent Functionalization

  • Francesco Amato1,2
  • Samuele De Santis1
  • Matteo Daino1
  • Leonardo Giaccari1
  • Alessandro Motta1,3
  • Mauro Giustini1
  • Francesca Anna Scaramuzzo4
  • Anita Scipioni1
  • Andrea Giacomo Marrani1
4 affiliations
  1. 1Sapienza Università di Roma , , P.le A. Moro 5 , ,
  2. 2ENEA, Casaccia Research Centre , , ,
  3. 3INSTM Consortium, UdR Roma , P.le A. Moro 5 , ,
  4. 4Sapienza Università di Roma , , Via del Castro Laurenziano 7 , ,
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Abstract

Graphene-based materials, including graphene oxide (GO), intrinsically lack stereocenters, limiting their usefulness in applications where chirality plays a crucial role. Covalent attachment of chiral molecules offers a promising strategy to introduce stereogenic elements into layers of GO. In this work, we report a one-pot method for the covalent functionalization of GO with lysine, exploiting the reactivity of the aminic groups of the amino acid toward epoxy groups located on the basal plane of the layers. Chirally functionalized layers of GO were prepared using d- and l-lysine and extensively purified to remove unreacted amino acid residuals. A comprehensive spectroscopic characterization confirms the successful functionalization, resulting in ∼3% N content. The chirality of the molecules bound to the resulting GO layers (relying on a rigorous purification by dialysis) was demonstrated through their interaction with a water-soluble porphyrin, which yielded chiral J-aggregates. The corresponding circular dichroism spectra confirmed that the porphyrin assemblies adopt distinct chiral configurations when templated by d- or l-GO. These findings highlight a straightforward route to impart chiral features to GO, expanding its applicability to several relevant fields, such as asymmetric catalysis, nanofiltration, and chiral sensing.

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Cite

BibTeXRIS
BibTeX
@article{amato2026introducing,
  title = {{Introducing Chirality into Graphene Oxide Layers through a Facile Amino Acid-Based Covalent Functionalization}},
  author = {Francesco Amato and Samuele De Santis and Matteo Daino and Leonardo Giaccari and Alessandro Motta and Mauro Giustini and Francesca Anna Scaramuzzo and Anita Scipioni and Andrea Giacomo Marrani},
  journal = {ACS Omega},
  year = {2026},
  month = oct,
  doi = {10.1021/acsomega.6c07448},
  url = {https://pubs.acs.org/acsodf/article/doi/10.1021/acsomega.6c07448/5458477/Introducing-Chirality-into-Graphene-Oxide-Layers},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - Introducing Chirality into Graphene Oxide Layers through a Facile Amino Acid-Based Covalent Functionalization
AU  - Francesco Amato
AU  - Samuele De Santis
AU  - Matteo Daino
AU  - Leonardo Giaccari
AU  - Alessandro Motta
AU  - Mauro Giustini
AU  - Francesca Anna Scaramuzzo
AU  - Anita Scipioni
AU  - Andrea Giacomo Marrani
PY  - 2026
DA  - 2026/10/26
JO  - ACS Omega
DO  - 10.1021/acsomega.6c07448
UR  - https://pubs.acs.org/acsodf/article/doi/10.1021/acsomega.6c07448/5458477/Introducing-Chirality-into-Graphene-Oxide-Layers
AB  - Graphene-based materials, including graphene oxide (GO), intrinsically lack stereocenters, limiting their usefulness in applications where chirality plays a crucial role. Covalent attachment of chiral molecules offers a promising strategy to introduce stereogenic elements into layers of GO. In this work, we report a one-pot method for the covalent functionalization of GO with lysine, exploiting the reactivity of the aminic groups of the amino acid toward epoxy groups located on the basal plane of the layers. Chirally functionalized layers of GO were prepared using d- and l-lysine and extensively purified to remove unreacted amino acid residuals. A comprehensive spectroscopic characterization confirms the successful functionalization, resulting in ∼3% N content. The chirality of the molecules bound to the resulting GO layers (relying on a rigorous purification by dialysis) was demonstrated through their interaction with a water-soluble porphyrin, which yielded chiral J-aggregates. The corresponding circular dichroism spectra confirmed that the porphyrin assemblies adopt distinct chiral configurations when templated by d- or l-GO. These findings highlight a straightforward route to impart chiral features to GO, expanding its applicability to several relevant fields, such as asymmetric catalysis, nanofiltration, and chiral sensing.
SN  - 2470-1343
ER  -