Reaction Steps
S-Acetylthio-derivatized triple decker (15). Samples of (Pc)Eu(Pc)Eu(E′B-Por) (28) (15 mg, 7.0 μmol), 4-iodo-1-(S-acetylthio)benzene (2.0 mg, 7.0 μmol), Pd2(dba)3 (1.0 mg, 1.1 μmol) and P(o-tolyl)3 (2.5 mg, 8.3 μmol) were added to a Schlenk flask. The flask was evacuated and purged with argon three times. Then deaerated toluene (3 mL) and deaerated N,N-diisopropylethylamine (0.6 mL) were added by syringe. The flask was immersed in an oil bath at 35° C. and stirred under argon. The reaction was monitored by TLC (silica, toluene) and LD-MS. After 24 h, the solvent was removed under vacuum, the residue dissolved in toluene/ether (60:1), and loaded onto a silica gel column packed with the same solvent. Elution with toluene/ether (60:1) afforded the desired product together with trace of unreacted starting material as the first band. The product thus obtained was further purified by a second column chromatography procedure (silica gel, toluene), affording a black solid (15) (3.1 mg, 19%) after removal of the solvent and washing with CH3OH. 1H NMR (CDCl3) δ 1.91 (m, 27H), 2.62 (s, 3H), 3.28 (m, 8H), 4.70-4.80 (m, 3H), 4.98 (d, J=6.6 Hz, 1H), 6.68 (m, 4H), 6.94 (d, J=6.6 Hz, 1H), 7.54 (m, 1H), 7.71 (m, 1H), 8.03 (m, 1H), 8.71 (brs, 8H), 9.05-9.12 (m, 3H), 9.42 (m, 1H), 10.10 (brs, 8H), 11.11 (brs, 8H), 11.56 (m, 2H), 11.72 (m, 1H), 12.02 (m, 1H), 12.98 (brs, 8H); LD-MS obsd 2291.4 (M+), 2250.2 (M+-CH3CO), 1181.0 (M+-(Por)Eu), 1111.6 (M+-(Pc)Eu(Pc)), 1067.8 (M+-(Pc)Eu(Pc)-CH3CO); FAB-MS obsd 2284.59, calcd exact mass 2284.58 (C130H90OSN20Eu2); λabs 341, 419, 523, 618, 721 nm.
