Different synthetic pathways leading to polythiophenes (PTs) containing units derived from methyl N-(tert-butoxycarbonyl)-S-3-thienyl- L-cysteinate (1) and methyl N-(tert-butoxycarbonyl)-S-(2-thien-3-ylethyl)-L-cysteinate (2) were investigated. The oxidative coupling with FeCl3 applied to N-deprotected monomer 1 generates a chemically fleeting PT, whereas when applied to N-deprotected monomer 2 generates a mixture of oligomers. Two co-polymers bearing cysteine moieties, poly{[methyl N-(tert-butoxycarbonyl)-S-3-thienyl-L-cysteinate]-cothiophene} (co-PT1) and poly{[methyl N-(tert-butoxycarbonyl)-S-(2-thien-3-ylethyl)-L-cysteinate]-co-thiophene} (co-PT2), were eventually synthesized through Stille coupling of 2,5-bis(trimethylstannyl)thiophene and 2,5-dibromo derivative of compound 1 and through the post-functionalization with protected cysteine of a tosylate co-polymer, poly{[2-(3-thienyl)ethyl 4-methylbenzenesulfonate]-co-thiophene} (co-PTTs). UV–vis, CD, NMR and GPC analyses evidenced that these polymers are able to form chiral self-assembling structures, due to the formation of a hydrogen bond network and to p-stacks, not only in the solid state but also in solution.

R. Cagnoli, M. Lanzi, A. Mucci, F. Parenti, L. Schenetti (2005). Polymerization of Cysteine Functionalized Thiophenes. POLYMER, 46, 3588-3596 [10.1016/j.polymer.2005.03.031].

Polymerization of Cysteine Functionalized Thiophenes

LANZI, MASSIMILIANO;
2005

Abstract

Different synthetic pathways leading to polythiophenes (PTs) containing units derived from methyl N-(tert-butoxycarbonyl)-S-3-thienyl- L-cysteinate (1) and methyl N-(tert-butoxycarbonyl)-S-(2-thien-3-ylethyl)-L-cysteinate (2) were investigated. The oxidative coupling with FeCl3 applied to N-deprotected monomer 1 generates a chemically fleeting PT, whereas when applied to N-deprotected monomer 2 generates a mixture of oligomers. Two co-polymers bearing cysteine moieties, poly{[methyl N-(tert-butoxycarbonyl)-S-3-thienyl-L-cysteinate]-cothiophene} (co-PT1) and poly{[methyl N-(tert-butoxycarbonyl)-S-(2-thien-3-ylethyl)-L-cysteinate]-co-thiophene} (co-PT2), were eventually synthesized through Stille coupling of 2,5-bis(trimethylstannyl)thiophene and 2,5-dibromo derivative of compound 1 and through the post-functionalization with protected cysteine of a tosylate co-polymer, poly{[2-(3-thienyl)ethyl 4-methylbenzenesulfonate]-co-thiophene} (co-PTTs). UV–vis, CD, NMR and GPC analyses evidenced that these polymers are able to form chiral self-assembling structures, due to the formation of a hydrogen bond network and to p-stacks, not only in the solid state but also in solution.
2005
R. Cagnoli, M. Lanzi, A. Mucci, F. Parenti, L. Schenetti (2005). Polymerization of Cysteine Functionalized Thiophenes. POLYMER, 46, 3588-3596 [10.1016/j.polymer.2005.03.031].
R. Cagnoli; M. Lanzi; A. Mucci; F. Parenti; L. Schenetti
File in questo prodotto:
Eventuali allegati, non sono esposti

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/11585/5595
 Attenzione

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

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 24
  • ???jsp.display-item.citation.isi??? 24
social impact