Characterization

 All final monomers were fully characterized by 1H NMR, 13C NMR, EI/HRMS,

and elemental analysis. The high molecular weight polymers were characterized using

H NMR, 13C NMR, GPC, and DSC.

Monomer Synthesis

Synthesis of 2-(undec-4-enoylamino)ethyl-undec-4-enoate (glycinol diene) (1).

 To a stirred solution of undecenyl acid (2.27 g, 14.7 mmol) in 55 mL CHC13 was

added ethanolamine (glycinol) (0.33 mL, 5.5 mmol); 1,3-diisopropylcarbodiimide (DIC)

(1.92 mL, 12.3 mmol); and 4-(dimethylamino)pyridine (DMAP) (0.13 g, 1.1 mmol) at 25

C in a 100 mL round bottom flask under an argon atmosphere. The reaction was

allowed to stir for 24 hours. The mixture was filtered to remove urea salts and the

remaining organic solution was washed successively with 1 M HC1 (2 x 20 mL);

saturated NaHCO3 solution (2 x 20 mL); and saturated NaCl solution (1 x 20 mL).

Solvent and volatile small molecules were removed from the washed organic layer by

vacuum evaporation resulting in a viscous oil. Upon cooling, the solid was recrystalized

three times from methanol and water. Overall yield for the resulting monomer (1) was

50%. H NMR (300 MHz, CDC13, ppm): 6 1.18-1.44 (m, 20H), 1.52-1.68 (m, 4H),

1.98-2.09 (q, 4H), 2.14-2.22 (t, 2H), 2.28-2.36 (t, 2H), 2.74-2.92 (m, 2H), 3.49-3.58 (m,

2H), 4.18-4.21 (m, 2H), 4.89-5.04 (m, 4H), 5.66-5.74 (s, 1H), 5.74-5.89 (m, 2H). 13C

NMR (75 MHz, CDC13, ppm): 6 25.45, 26.29, 29.52, 29.71 29.76, 29.84, 29.90, 29.93,

34.41, 34.81, 37.39, 39.45, 63.77, 114.80, 114.82, 139.80, 173.82, 174.63. Elemental

Analysis (C,H,N): Theoretical: (73.24, 11.01, 3.56). Found: (73.17, 11.12, 3.71).

EI/HRMS [M + 1]: Calculated for C24H43N03: 394.3243 g/mol. Found: 394.3302.