The title compound was prepared by the regioselective homocoupling of 10-methoxyazuleno[2,1-c]phenanthrene in the presence of ammonium persulfate. The structure of the synthesized compound was assigned on the basis of its 1 H-NMR, FT-IR, and mass spectral data. Its crystal structure and electrochemical properties are also reported. 10,phenanthrene (2) 10-Methoxyazuleno[2,1-c]phenanthrene (1) was synthesized according to our previously reported method [3]. Under an argon atmosphere, a mixture of compound 1 (50 mg, 0.16 mmol) and APS (183 mg, 0.80 mmol) in degassed toluene (25 mL) was heated at 100 °C for 1 h. Additional APS (183 mg, 0.80 mmol) was added and the mixture was stirred for 2 h at 100 °C. After cooling to room temperature, the reaction mixture was washed with brine, and extracted with CHCl3. The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel 60N (spherical neutral, 40-50 µm, Kanto Chemical Co., Inc., Hexane/AcOEt = 50:1) to give 2 (40 mg, 80% yield) as a green solid. Synthesis ofMelting point: no change until 300 °C.FT-IR (neat): νmax (cm −1 ): 2922, 1571, 1499, 1446, 1261, 1218, 954, 834, 789, 758, 729, 697, 682. 1 H-NMR (CDCl3, 500 MHz): δ9.54 (d, J = 7.7 Hz, 2H), 9.35 (d, J = 8.2 Hz, 2H), 7.99 (dd, J = 8.0, 0.9 Hz, 2H), 7.86 (br d, J = 8.0 Hz, 2H), 7.80 (d, J = 8.5 Hz, 2H), 7.74 (br s, 2H), 7.60 (dt, J = 7.0, 1.0 Hz, 2H), 7.52 (t, J = 7.4 Hz, 2H), 7.34 (br t, J = 9.8 Hz, 4H), 6.75 (t, J = 9.7 Hz, 2H), 6.55 (br s, 2H), 3.12-3.25 (m, 6H). HRMS (ESI-TOF): [M] + calcd for C46H30O2 614.2240; found 614.2210.