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Chemoenzymatic Synthesis of Fluorescent and Colored Polyesters
Author(s) -
Navarra Cristina,
Marzorati Mattia,
Danieli Bruno,
Riva Sergio
Publication year - 2011
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201000327
Subject(s) - amine gas treating , chemistry , amide , polyester , polymerization , primary (astronomy) , fluorescence , combinatorial chemistry , catalysis , organic chemistry , polymer , polymer chemistry , caprolactone , protecting group , physics , quantum mechanics , astronomy , alkyl
Abstract A simple chemoenzymatic strategy for the synthesis of colored and fluorescent poly(ε‐caprolactone) esters has been developed. The procedure involves first the reaction of a functionalized primary amine with ε‐caprolactone, to give an amide with a terminal primary hydroxy group, followed by an enzymatic ring‐opening polymerization catalyzed by Novozym 435. The proposed method is easy to handle and is suitable for the incorporation of different amines, as it shown for the yellow compound N ‐deacetylthiocolchicine and the fluorescent amines 4‐(2‐aminoethylamino)‐7‐( N , N ‐dimethylsulfamoyl)benzofurazan and dansylcadaverine. A similar strategy is considered for the synthesis of poly(ε‐caprolactone) esters, employing alcohols as initiators of the reaction. In this case, an intermediate ester carrying a terminal primary hydroxy group cannot be isolated and the reaction forms directly the desired polymers.