solution was filtered and the filtrate was evaporated. The crude solids were purified by chromatography
(silica gel, 30% THF/hexane) to give 11 ( 425 mg, 52.7%) as a bright orange solid.
A mixture of 11 (280 mg, 0.35 mmol), Zn(OAc)2 (24 mg, 0.13 mmol) and 1.8-diazabicyclo[5.4.0]-
undec-7-ene (0.2 mL) in n-pentanol (5 mL) was heated to reflux for 12 h. After the solution was cooled it
was diluted with MeOH and the black precipitates were filtered. The crude solids were purified by
chromatography(silica gel, 50% THF/hexane) to give 1 (140 mg, 49%) as a green solid. The
octadecyloxy group substituted phthalocyanine (2) was synthesized by similar procedure like as 1.
The characterizations of 11, 12, 1 and 2.
Compound (11) : 52.7 % yield; Rf = 0.4 (THF : Hexane = 1 : 3); mp 145-146 ℃(recrystallized from
1
ethanol); FT-IR (KBr) : ν = 2921, 2852, 2233, 1581, 1488, 1241, 1145 cm-1; H-NMR (CDCl3, 400
MHz) : δ = 8.00 ~ 7.90 (m, 10H), 7.25 ~ 7.14 (m, 4H), 7.06 ~ 6.85 (m, 4H), 4.08 (t, J=6.4 Hz, 4H), 1.80
(m, 4H), 1.40 ~ 1.20 (m, 24H), 0.90 (t, J=7.1 Hz, 6H); Anal. Calcd for C50H56N6O4 : C 74.60, H 7.01, N
10.44. Found C 74.53, H 7.03, N 10.47.
Compound (12) : 60.5 % yield; Rf = 0.5 (THF : Hexane = 1 : 5); mp 133-134 ℃(recrystallized from
1
ethanol); FT-IR (KBr) : ν = 2917, 2850, 2233, 1581, 1490, 1245, 1145 cm-1; H-NMR (CDCl3, 400
MHz) : δ = 8.10 ~ 7.90 (m, 10H), 7.21 ~ 7.15 (m, 4H), 7.03 ~ 6.99 (m, 4H), 4.08 ~ 4.03 (t, J=6.3 Hz, 4H),
1.85~1.80 (m, 4H), 1.59 ~ 1.13 (m, 60H), 0.90 ~ 0.88 (t, J=7.2 Hz, 6H); Anal. Calcd for C68H92N6O4 : C
77.23, H 8.77, N 7.95. Found C 77.16, H 8.80, N 7.99.
Compound (1) : 49 % yield; Rf = 0.5 (THF : Hexane = 1 : 3); mp >368 ℃(decomp, recrystallized from
ethanol); FT-IR (KBr) : ν = 2923, 2852, 1598, 1492, 1430, 1392, 1245, 1145 cm-1; 1H-NMR (CDCl3, 400
MHz) : δ = 7.86 ~ 7.46 (s , 40H), 7.11 ~ 6.72 (s, 32H), 3.95 (s, 16H), 1.79(s, 16H) 1.56~1.20 (m, 96H),
0.92 (t, J=7.1 Hz 24H); UV/VIS (CHCl3, 10-5): λmax (nm) [ε] = 249[37910], 286[35030], 358[79850],
614[18620], 681[100990]; MALDI–TOF MS : m/z 2136, 2068, 1820, 1815, 574; Anal. Calcd for
C200H224N24O16Zn : C 73.11, H 6.87, N 10.23. Found C 73.20, H 6.79, N 10.19.
Compound (2) : 56 % yield; Rf = 0.5 (THF : Hexane = 1 : 2); mp >379 ℃(decomp, recrystallized from
1
ethanol); FT-IR (KBr) : ν = 2921, 2850, 1598, 1492, 1392, 1247, 1145 cm-1; H-NMR (CDCl3, 400
MHz) : δ = 8.20 ~ 7.45 (s , 40H), 7.10 ~ 6.70 (s, 32H), 3.94 (s, 16H), 1.78(s, 16H) 1.60 ~ 0.98 (m, 240H),
0.87 (t, J=7.2 Hz, 24H); UV/VIS (CHCl3, 10-5): λmax (nm) [ε] = 251[34040], 285[23030], 360[79730],
615[10420], 683[89300]; MALDI–TOF MS : m/z 3914, 3438, 2960, 2583, 2220, 574. Anal. Calcd for
C272H368N24O16Zn : C 76.06, H 8.64, N 7.83. Found C 76.17, H 8.57, N 7.91.
ACKNOWLEDGEMENTS
The authors thank the Ministry of Education of Korea for financial support (BK 21 program).