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. 2021 Dec 1;122(1):565–788. doi: 10.1021/acs.chemrev.1c00449

Scheme 77. Synthesis of Benzene-Fused Se-Annulated PDI Dimers and Trimers.

Scheme 77

Reagents and conditions: (a)148 1,3,5-benzenetriboronic acid tris(pinacol)ester, Pd(PPh3)4, Na2CO3, 2:1 THF/H2O, reflux, 48 h, 91%; (b) I2, toluene, hν (Hg lamp), rt, 24 h, 93%; (c) HNO3 (fuming), DCM, rt, 12 h, quant.; (d) selenium powder, NMP, 190 °C, 12 h, 87%; (e)149 Pd(PPh3)4, K2CO3, 2:1 THF/H2O, 85 °C, 13 h, 75%; (f) I2, DCM, hν (sunlight), rt, 8 h, 80%; (g) ClSO3H, rt, 4 h, quant.; (h) 6-undecylamine or 12-tricosylamine, imidazole, 150 °C, 4 h, 41%.