Polymerization of cysteine functionalized thiophenes |
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Authors: | Rita Cagnoli Adele Mucci Luisa Schenetti |
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Affiliation: | a Dipartimento di Chimica, Centro SCS, Università di Modena e Reggio Emilia, via G. Campi 183, 41100 Modena, Italy b Dipartimento di Chimica Industriale e dei Materiali, Università di Bologna, viale Risorgimento 4, 40136 Bologna, Italy |
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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]-co-thiophene} (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 π-stacks, not only in the solid state but also in solution. |
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Keywords: | Polythiophenes Cysteine Stille coupling |
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