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. 2023 May 15;13(12):3551–3557. doi: 10.1039/d3cy00284e

Catalytic conditions for the synthesis of polyureas from diformamides and diaminesa.

graphic file with name d3cy00284e-u1.jpg
Entry Diformamide Diamine Base Solvent N2 Yield/% M n (MALDI) Al : Ar T d/°C T m/°C
1 DF1 DA1 KOtBu THF Sealed 82 1877 1.67 246 221
2 DF1 DA1 KOtBu Anisole Sealed 77 2111 1.03 246 220
3 DF1 DA1 KOtBu Anisole Open 32 2111 1.67 237 201
4 DF1 DA1 KOtBu Diglyme Open 79 1904 2.01 238 212
5 DF1 DA1 KOtBu DMSO Open 44 4.88 266 211
6 DF1 DA1 K2CO3 Anisole Open 30 1770 1.73 242 204
7 DF2 DA1 KOtBu Anisole Open 85 2111 N/A 253 216
8 DF2 DA1 KOtBu Diglyme Open 25 2110 N/A 213 210
9 DF2 DA1 KOtBu THF Open 78 2594 N/A 247 215
10 DF1 DA2 KOtBu Anisole Open 94 3140b 1.16 223
a

Catalytic conditions: diamine (0.5 mmol), diformamide (0.5 mmol), solvent (2 mL), complex 1 (2 mol%), and KOtBu (8 mol%). Al : Ar = aliphatic : aromatic NMR integral relationship. Mn (MALDI, g mol−1): value is estimated as the maximum signal observed in MALDI FT-ICR mass spectrometry. Td (decomposition temperature) was recorded at 5% mass loss. Tm stands for melting temperature.

b

M n of 44 000 g mol−1 was estimated using GPC.