Dipeptides are popular building blocks for supramolecular gels that do not persist in the environment and may find various applications. In this work, we show that a simple substitution on the aromatic side-chain of phenylalanine with either fluorine or iodine enables supramolecular diversity upon self-assembly at neutral pH, leading to hydrogels or crystals. Each building block is characterized by H-1- and C-13-NMR spectroscopy, LC-MS, circular dichroism, and molecular models. The supramolecular behaviour is monitored with a variety of techniques, including circular dichroism, oscillatory rheology, transmission electron microscopy, attenuated total reflectance Fourier-transformed infrared spectroscopy, visible Raman spectroscopy, synchrotron-radiation single-crystal X-ray diffraction and UV Resonance Raman spectroscopy, allowing key differences to be pinpointed amongst the halogenated analogues.

Single-atom substitution enables supramolecular diversity from dipeptide building blocks

Scarel, Erica;Bellotto, Ottavia;Rozhin, Petr;Kralj, Slavko;De Zorzi, Rita;Marchesan, Silvia
2022-01-01

Abstract

Dipeptides are popular building blocks for supramolecular gels that do not persist in the environment and may find various applications. In this work, we show that a simple substitution on the aromatic side-chain of phenylalanine with either fluorine or iodine enables supramolecular diversity upon self-assembly at neutral pH, leading to hydrogels or crystals. Each building block is characterized by H-1- and C-13-NMR spectroscopy, LC-MS, circular dichroism, and molecular models. The supramolecular behaviour is monitored with a variety of techniques, including circular dichroism, oscillatory rheology, transmission electron microscopy, attenuated total reflectance Fourier-transformed infrared spectroscopy, visible Raman spectroscopy, synchrotron-radiation single-crystal X-ray diffraction and UV Resonance Raman spectroscopy, allowing key differences to be pinpointed amongst the halogenated analogues.
2022
Pubblicato
https://pubs.rsc.org/en/content/articlelanding/2022/sm/d1sm01824h
File in questo prodotto:
File Dimensione Formato  
Scarel_SoftMatter2022.pdf

Accesso chiuso

Tipologia: Documento in Versione Editoriale
Licenza: Copyright Editore
Dimensione 4.43 MB
Formato Adobe PDF
4.43 MB Adobe PDF   Visualizza/Apri   Richiedi una copia
d1sm01824h1.pdf

accesso aperto

Descrizione: supplementary files
Tipologia: Altro materiale allegato
Licenza: Digital Rights Management non definito
Dimensione 4.4 MB
Formato Adobe PDF
4.4 MB Adobe PDF Visualizza/Apri
Scarel_SoftMatter2022-Post_print.pdf

Open Access dal 02/02/2023

Tipologia: Bozza finale post-referaggio (post-print)
Licenza: Digital Rights Management non definito
Dimensione 4.97 MB
Formato Adobe PDF
4.97 MB Adobe PDF Visualizza/Apri
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11368/3014859
Citazioni
  • ???jsp.display-item.citation.pmc??? 3
  • Scopus 7
  • ???jsp.display-item.citation.isi??? 7
social impact