Scheme 3. Synthetic Route toward the Key Building Block 11,11′-Dibromo-5,5′-bischrysene 5.
Reagents and conditions: (a) PdCl2(PPh3)2, CuI, Et3N, THF, rt, 24 h, 7a: 82%, 7b: 85%. (b) n-BuLi, THF, ICH2CH2I, −78 °C to rt, 8a: 88%, 8b: 90%. (c) CuCl, DMF, Air, 80 °C, 6 h, 9a: 78%, 9b: 83%. (d) Pd(PPh3)4/Na2CO3, THF/H2O/EtOH, 60 °C, 24h, 11a: 50%, 11b: 56%. (e) PtCl2, Toluene, 85 °C, 24 h, 5a: 70%, 5b: 78%.