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 eventuallysynthesized 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.

Polymerization of Cysteine Functionalized Thiophenes / Cagnoli, Rita; M., Lanzi; Mucci, Adele; Parenti, Francesca; Schenetti, Luisa. - In: POLYMER. - ISSN 0032-3861. - STAMPA. - 46:11(2005), pp. 3588-3596. [10.1016/j.polymer.2005.03.031]

Polymerization of Cysteine Functionalized Thiophenes

CAGNOLI, Rita;MUCCI, Adele;PARENTI, Francesca;SCHENETTI, Luisa
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 eventuallysynthesized 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
46
11
3588
3596
Polymerization of Cysteine Functionalized Thiophenes / Cagnoli, Rita; M., Lanzi; Mucci, Adele; Parenti, Francesca; Schenetti, Luisa. - In: POLYMER. - ISSN 0032-3861. - STAMPA. - 46:11(2005), pp. 3588-3596. [10.1016/j.polymer.2005.03.031]
Cagnoli, Rita; M., Lanzi; Mucci, Adele; Parenti, Francesca; Schenetti, Luisa
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/458527
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