SUPPLEMENTARY INFORMATION. Isomannide-Containing Poly(butylene 2,5-furandicarboxylate) Copolyesters via Ring Opening Polymerization

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1 SUPPLEMENTARY INRMATIN Isomnnide-Contining Poly(butylene 2,5-furndirboxylte) Copolyesters vi Ring pening Polymeriztion Jun Crlos Morles-Huert, 1 Antxon Mrtínez de Ilrduy 1 Slvdor León 2 nd Sebstián Muñoz-Guerr 1* 1 Deprtment d Enginyeri Quími, Universitt Politèni de Ctluny, ETSEIB, Digonl 647,8028 Brelon, Spin 2 Deprtmento de Ingenierí Quími, Universidd Politéni de Mdrid, ETSIIM, Gutiérrez Absl 2, Mdrid, Spin Correspondene to: S. Muñoz-Guerr (E-mil: sebstin.munoz@up.edu) Additionl Supporting Informtion (SI) my be found in the online version of this rtile. Contents: igure S1. ) 1 H NMR, b) HPLC nd ) MALDI T of (B) n. igure S2. 1 H NMR of the rude produt obtined in the yliztion retion of Im nd DCA-Cl 2 showing the presene of both yli nd liner oligomeri speies. igure S3. 1 H NMR of the retion produt obtined in the ondenstion of Is with DCA-Cl 2. igure S4. Reltive energy (kl mol -1 residue) of yli oligo(isohexide furnote) determined by energy minimiztion with pplition of the GRMACS fore-field nd tken s referene the orresponding liner speies.(simultion detils nd referenes). igure S5. 1 H NMR spetr of the whole series of opb x Im y opolyesters with indition of signl ssignments. igure S6. Powder XRD profiles reorded from semirystlline opb x Im y nd the PB nd PIm homopolyesters. Spings indited in Å. igure S7. Polrizing optil mirogrphs of thin films of PB nd semirystlline opb x Im y. igure S8. DSC tres of PB, PIm nd opb x Im y opolyesters showing the infletions due to glss-trnsitions.

2 ) CDCl 3 b C C C C n b b) (B) 2 (B) 3 CHCl 3 (B) time (min) ) % Intensity (B) 2 +N (B) 3 +N 210 (B) 4 +N (B) 5 +N mss (m z -1 ) igure S1. ) 1 H NMR, b) HPLC nd ) MALDI T of (B) n.

3 CHCl 3 b e n-1 e e end end b b end igure S2. 1 H NMR of rude (Im) n. CHCl 3 f H e i h d I Hg h end, d end * f e, l h, d g e end,l end igure S3. 1 H NMR of liner oligomers of PIs.

4 Energy(kl mol residue -1 ) n (Id) n (Is) n (Im) n igure S4. Reltive energy (kl mol -1 residue -1 ) of yli oligo(isohexide furnote)s vs size of the yle size determined by energy minimiztion with pplition of the GRMACS fore-field nd tken s referene the orresponding liner speies. Simultion detils: Clssil moleulr mehnis minimiztions hve been rried out on liner nd yli oligomers with the GRMS fore-field 1, nd the orresponding energy prmeters hve been obtined with the Atomisti Topology Builder (ATB) online tool. 2 The geometry of the yli oligomers (Im) n, (Is) n nd (Id) n with n rnging from 2 to 5 ws optimized, nd the reltive energy by monomer ws omputed reltive to the orresponding liner polymer. The modelling ws performed with the GRMACS softwre ostenbrink, C.; Vill, A.; Mrk, A.E.; vn Gunsteren, W.. J. Comput. Chem. 2004, 25, ) Mlde, A.K.; Zuo, L.; Breeze, M.; Stroet, M.; Poger, D.; Nir, P.C.; ostenbrink, C.; Mrk, A.E.; J. Chem. Theory Comput. 2011, 7, ; b) Cnzr, S.; El-Kebir, M.; Pool, R.; Elbssioni, K.; Mlde, A.K.; Mrk, A.E.; Geerke, D.P.; Stougie, L.; Klu, G.W. J. Comput. Biol. 2013, 20, ; ) Kozir, K.B.; Stroet, M.; Mlde, A.K.; Mrk, A.E. J. Comp. Aided Mol. De. 2014, 28, Eihenberger, A.P.; Allision, J.R.; Dolen, J.; Geerke, D.P.; Hort, B.A.C.; Meier, K.; ostenbrink, C.; Shmid, N.; Steiner, D.; Wng, D.Q.; vn Gunsteren, W.. J. Chem. Theory Comput. 2011, 7,

5 h f i e f H g i d f f H i i f, i f i g i h i d f e f PB opb 95 Im 5 opb 90 Im 10 opb 80 Im 20 opb 70 Im 30 opb 60 Im 40 opb 50 Im 50 PIm igure S5. 1 H NMR spetr of the whole series of opb x Im y opolyesters with indition of signl ssignments.

6 PB d (Å) opb 95 Im 5 opb 90 Im 10 PIm igure S6. Powder XRD profiles reorded from semirystlline opb x Im y nd the PB nd PIm homopolyesters. Spings indited in Å. igure S7. Polrizing optil mirogrphs of thin films of PB nd semirystlline opb x Im y. PB opb 95 Im 5 endo opb 90 Im 10 opb 80 Im 20 opb 70 Im 30 opb 60 Im 40 opb 50 Im 50 PIm Temperture ( o C) igure S8. DSC tres of PB, PIm nd opb x Im y opolyesters showing the infletions due to glss-trnsition.