1.1 Porphyrins - Friedrich-Alexander-Universität Erlangen-Nürnberg

6 Experimental Section
UV/Vis (CH2Cl2): λ [nm] (ε [M -1 ·cm -1 ]) = 421 (381000), 517 (20000), 553 (9300), 593 (5800),
648 (4200).
EA: C59H56N6O2·H2O. Calc.: C 78.81, H 6.50, N 9.35; found: C 79.07, H 6.47, N 9.15.
6.2.6.5 5 4 ,10 4 ,20 4 -Tri-t-Butyl-5 6 -Methyl-15 4 -Nitro-5,10,15,20-Tetraphenylporphyrin-5 2 -
HO 2 C
182
Ethanoic Acid, 90
According to GP II, 120 mg (136 μmol) of cyanomethyl
porphyrin 89 are brought to reaction in glacial HOAc
(15 mL), conc. H2SO4 (15 mL) and water (5 mL). Pure 90,
obtained after FC over silica with CH2Cl2 and ethyl acetate
as eluent (ratio: 7 : 3), appears as a violet powder in
113 mg (126 μmol) yield, equiv. to 92 % based on 89.
1 H NMR (400 MHz, rt, CDCl3): δ [ppm] = -2.74 (s, 2 H, NH), 1.50 (s, 18 H, t-BuH), 1.53 (s, 9 H,
t-BuH), 1.80 (s, 3 H, CH3), 3.21 (s, 2 H, CH2), 7.50 (m, 4 H, ArH+Ar’H), 7.69 (d, 3 J = 7.8 Hz, 4 H,
ArH), 7.94 (d, 3 J = 7.8 Hz, 2 H, ArH), 8.06 (d, 3 J = 7.8 Hz, 2 H, ArH), 8.35 (d, 3 J = 7.8 Hz, 2 H,
Ar’’H), 8.61 (m, 4 H, Ar’’H+β-H), 8.68 (d, 3 J = 4.8 Hz, 2 H, β-H), 8.76 (d, 3 J = 4.6 Hz, 2 H, β-H),
8.86 (d, 3 J = 4.6 Hz, 2 H, β-H).
13 C NMR (100.5 MHz, rt, CDCl3): δ [ppm] = 22.0, 31.5, 34.7, 39.7, 116.6, 117.4, 120.6, 121.8,
123.7, 124.1, 125.5, 130.4 (br), 131.8 (br), 134.4, 134.5, 134.9, 135.2, 138.4, 138.7, 139.6,
147.7, 149.5, 150.7, 151.6, 176.0.
MS (FAB+, NBA): m/z (%) = 900 (100) [M] +· .
IR (ATR): 𝜈� [cm -1 ] = 3321, 2963, 2906, 2868, 1712, 1595, 1560, 1519, 1474, 1400, 1362, 1340,
1310, 1269, 1223, 1210, 1186, 1110, 1021, 993, 982, 968, 919, 849, 800, 738.
UV/Vis (CH2Cl2): λ [nm] (ε [M -1 ·cm -1 ]) = 421 (369000), 518 (19600), 553 (10100), 593 (6300),
649 (4900).
N
NH HN
N
90
C 59 H 57 N 5 O 2
M = 900.11 g·mol -1
NO 2
EA: C59H57N5O4·EtOAc·1.5 H2O. Calc.: C 74.53, H 6.75, N 6.90; found: C 74.15, H 6.61, N 7.15.