Reaction Steps
To a mixture of 1,2,3,4,8,12,13,14,15,19-deca(4′-t-butylphenylthio)-6,10,17,21-tetrahydro-6,10,17,21-tetra(2′,6′-dimethylphenyl)nonacene-6,10,17,21-tetraol (0.04 g, 0.015 mmol) in 1,4-dioxane (10 mL) was added anhydrous SnCl2 (0.1 g, 0.52 mmol). To this suspension was added 10% HCl (1 mL) in complete darkness and the resulting mixture was stirred at room temperature for 0.5 h under Ar. Upon completion of the reaction, black precipitates were filtered in the dark light under N2. The solids were washed with water (50 mL) followed by methanol to yield persistent nonacene derivative 1,2,3,4,8,12,13,14,15,19-deca(4′-t-butylphenylthio)-6,10,17,21-tetra(2′,6′-dimethylphenyl)nonacene as a black solid. 1H NMR (500 MHz, CDCl3): δ 8.83 (s, 4H), 8.74 (s, 4H), 7.14 (m, 20H), 7.08 (m, 10H), 7.00 (m, 10H), 6.72 (m, 8H), 6.66 (m, 4H), 1.96 (s, 24H), 1.23 (bs, 90H). 13C NMR (125.68 MHz, CDCl3): δ 148.9, 148.7, 148.5, 148.4, 143.5, 143.4, 142.9, 137.7, 137.1, 136.0, 134.2, 133.7, 131.4, 131.3, 130.9, 128.7, 128.4, 128.2, 128.0, 127.9, 127.5, 127.2, 126.1, 126.1, 126.0, 126.0, 34.50, 34.48, 31.51, 31.45, 31.4, 19.9. LDI-MS m/z: 2536 [M+], UV-vis λmax (nm): 550, 600, 655, 716, 846, 921, 1033. The 1H NMR spectrum of 1,2,3,4,8,12,13,14,15,19-deca(4′-t-butylphenylthio)-6,10,17,21-tetra(2′,6′-dimethylphenyl)nonacene and the compound structure are shown in FIGS. 17A & B.
