Reaction Steps
The general procedure was used to couple 5,15-dibromo-10,20-di(3,5-di-tert-butylphenyl)porphyrin (0.043 g, 0.05 mmol) with R-(+)-1,1′-bi-2-naphthol (0.167 g, 0.58 mmol), using Pd2(dba)3 (0.0046 g, 0.005 mmol) and DPEphos (0.0107 g, 0.02 mmol) in the presence of Cs2CO3 (0.0652 g, 0.2 mmol). The reaction was conducted in toluene (5 mL) at 100° C. for 20 h. The title compound was isolated by flash column chromatography (silica gel, ethyl acetate:hexanes (v/v)=1:5) as purple solids (0.022 g, 35%). 1H NMR (300 MHz, CDCl3): δ 9.21 (d, J=4.8 Hz, 4H), 8.77 (d, J=4.8 Hz, 4H), 7.37-8.05 (m, 26H), 7.07 (d, J=16.2 Hz, 2H), 6.49 (d, J=9.6 Hz, 2H), 5.66 (s, 2H), 1.51 (m, 36H), −2.45 (s, 2H). 13C NMR (75 MHz, CDCl3): δ 161.2, 151.9, 149.0, 140.0, 134.4, 133.9, 131.7, 130.8, 130.3, 129.7, 129.6, 128.9, 128.6, 128.4, 127.9, 127.4, 127.0, 125.2, 125.0, 123.7, 121.3, 117.8, 117.2, 114.5, 35.0, 31.7. UV-vis (CHCl3, λmax, nm): 425, 521, 558, 598, 655. HRMS-MALDI ([M+H]+): calcd for C88H79N4O4, 1255.6096, found 1255.6045 with an isotope distribution pattern that is the same as calculated one.
