Conformational Control of a Polyether-Linked Porphyrin Dimer Induced by Complexation with a Sodium Cation

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• 1a 1H NMR (500 MHz, CDCl3) δ 0.96 (t, J = 7.6 Hz, 12H), 1.26–1.51 (m, 24H), 1.87 (quint, J = 7.6 Hz, 8H), 2.89 (t, J = 7.6 Hz, 8H), 3.68–3.75 (m, 8H), 3.94 (m, 4H), 4.07 (s, 6H), 4.28 (m, 4H), 7.22–7.28 (m, 8H), 7.46 (d, J - 7.9 Hz, 8H), 8.02–8.09 (m, 16H), 8.89–8.91 (m, 16H); FAB MS m/z 1938 (M+), 1939 (MH+), 1940 (MH+ +1), 1941 (MH+ +2), 1942 (MH+ +3), 1943 (MH+ +4), 1994 ((MH+ +5); Anal. Calcd for C122H122N8O7Zn2: C, 75.41; H, 6.33; N, 5.77. Found: C, 75.15; H, 6.42; N, 5.41. 1b 1H NMR (500 MHz, CDCl3/CD3CN = 7/3, v/v) δ 0.96 (t, J = 7.6 Hz, 12H), 1.26 -1.53 (m, 24H), 1.86 (quint, J = 7.6 Hz, 8H), 2.87 (t, J = 7.6 Hz, 8H), 3.72–3.79 (m, 12H), 3.93 (t, J = 4.3 Hz, 4H), 4.02 (s, 6H), 4.25 (t, J = 4.3 Hz), 7.14 (d, J = 8.6 Hz, 4H), 7.19 (d, J = 8.2 Hz, 4H), 7.43–7.44 (m, 8H), 7.97–8.04 (m, 16H), 8.81–8.85 (m, 16H); FAB MS m/z 1982 (M+), 1983 (MH+), 1984 (MH+ +1), 1985 (MH+ +2), 1986 (MH+ +3), 1987 (MH+ +4), 1988 ((MH− +5); Anal. Calcd for C124H126N8O8Zn2: C, 74.95; H, 6.39; N, 5.64. Found: C, 74.81; H, 6.64; N, 5.30.
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• Here a sodium cation was chosen as a guest because sodium perchlorate shows better solubility to the solvent employed here than the other alkali and alkaline earth metal salts.
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• The standard deviations for complexation of 1a 1b with NaClO4 are less than 3%.
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• The value of K for complexation of 2 with is 4620 ± 1020 M−1. This relatively large value is probably due to the absence of the steric repulsion of the porphyrin ring.
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