Cyclic peptoids are biocompatible/biodegradable cyclooligomers constituted byN-substituted glycines showing high binding constants with the first group alkali metals (Ka∼ 106for Na+, Li+and K+) in organic solvents. Three new metallated species bearingN-benzyl groups as side chains (a cyclic pentamer, [1·2Na]2+, and two cyclooctamer [3·Na]+and [3·2Na]2+peptoids) were synthesized together with the knownN-perbenzylated sodiated cyclohexamer [2·Na]+and [2·2Na]2+. Na+complexes were investigated by means of spectroscopic (NMR), computational (DFT) and X-ray crystallographic studies. The first application of these complexes as catalysts in the ring opening polymerization (ROP) ofl-lactide (l-LA) was examined. Our studies suggest that, for the intrinsic properties of the catalytic site (revealed by steric topographic maps) the homooligomeric pentamer complex [1·2Na]2+is the most active member of the cyclooligomeric family.

Synthesis and characterization of new Na+complexes ofN-benzyl cyclic peptoids and their role in the ring opening polymerization ofl-lactide

D'Amato A.;Schettini R.;Pierri G.;Izzo I.;Grisi F.;Tedesco C.;De Riccardis F.;Costabile C.
2021

Abstract

Cyclic peptoids are biocompatible/biodegradable cyclooligomers constituted byN-substituted glycines showing high binding constants with the first group alkali metals (Ka∼ 106for Na+, Li+and K+) in organic solvents. Three new metallated species bearingN-benzyl groups as side chains (a cyclic pentamer, [1·2Na]2+, and two cyclooctamer [3·Na]+and [3·2Na]2+peptoids) were synthesized together with the knownN-perbenzylated sodiated cyclohexamer [2·Na]+and [2·2Na]2+. Na+complexes were investigated by means of spectroscopic (NMR), computational (DFT) and X-ray crystallographic studies. The first application of these complexes as catalysts in the ring opening polymerization (ROP) ofl-lactide (l-LA) was examined. Our studies suggest that, for the intrinsic properties of the catalytic site (revealed by steric topographic maps) the homooligomeric pentamer complex [1·2Na]2+is the most active member of the cyclooligomeric family.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

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/11386/4768324
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 0
  • ???jsp.display-item.citation.isi??? 0
social impact