Supplementary material

Functional polylactide via ring-opening copolymerisation with allyl, benzyl and propargyl glycidyl ethers

Gwenaelle Pound-Lana1*, Jean-Michel Rabanel2, Patrice Hildgen2, Vanessa Carla Furtado

Mosqueira1

1 Laboratório de Desenvolvimento Galênico e Nanotecnologia, Universidade Federal de Ouro

Preto, Campus Universitário Morro do Cruzeiro, Ouro Preto, MG 35400-000, Brazil

2 Laboratoire de Nanotechnologie pharmaceutique, Faculty of Pharmacy, Université de

Montréal, Montréal, QC H3T 1J4, Canada

*corresponding author gpoundlana@gmail.com

1. NMR characterization of alkyne-functional polylactide, azidocoumarin and poly(lactide-co-propargyl glycidyl ether)-coumarin conjugate in CDCl3

Figure 1: 2D-homonuclear correlation spectroscopy (COSY) and 13C-NMR spectra of a copolymer of lactide and propargyl glycidyl ether (PGE) obtained with 46 mol% PGE in the feed

Figure 2: Heteronuclear single-quantum correlation (HSQC) spectrum

Figure 3: 1H-NMR spectra of copolymers of lactide obtained with increasing propargyl glycidyl ether (PGE) content in the feed.

Figure 4: 1H-NMR spectra of 3-(α-azidoacetyl)coumarin and its polymer-conjugate obtained via Cu(I)-catalyzed cycloaddition with alkyne-functional polylactide.

2. Photochemical characterization of the azide-functional coumarin and its synthetic precursor.

Figure 5: schematic scheme for the synthesis of 3-(α-azidoacetyl)coumarin according to [1] and its UV-Vis (left) and fluorescence (right) spectra in acetonitrile.

The molar absorptivity values at the maximum UV absorption wavelength (304 nm), were 13500 and 12900 mol-1·L-1·cm-1 for 3-(bromoacetyl)coumarin and 3-(α-azidoacetyl)coumarin, respectively. The brominated coumarin precursor did not show luminescent properties, whereas the 3-(α-azidoacetyl)coumarin showed strong fluorescence in acetonitrile with excitation and emission maxima of 450 and 510 nm, respectively.

[1] R.A. Kusanur, M.V. Kulkarni, New 1,3-dipolar cycloadducts of 3-azidoacetylcoumarins with DMAD and their antimicrobial activity, Indian Journal of Chemistry Section B-Organic Chemistry Including Medicinal Chemistry 44(3) (2005) 591-594.