1.1 Porphyrins - Friedrich-Alexander-Universität Erlangen-Nürnberg

9.0 8.8 8.6 8.4 8.2 8.0 7.8
Discussion and Results 3
Since all those systems are of high symmetry (D2h), the corresponding NMR spectra appear
quite simple. Furthermore are 49 and 79 already known to literature 69,70b , so that the
discussion will focus on 78 whose 1 H NMR spectrum is displayed in Figure 43. The data on 79
is included in the experimental section.
3, 7,
13, 17
2, 8,
12, 18
*
m-Ar’H
o-ArH m-ArH
CH 2
9 8 7 6 5 4 3 2 1 0 -1 δ [ppm] -3
10 4
20 4
5 4
15 4
*
NC
CN
N
NH HN
Figure 43. 1 H NMR spectrum of 78 measured at 400 MHz in CDCl3 at rt. Signals are numbered
according to IUPAC recommendations. (Ar’ = functionalized phenyl rings)
The β-pyrrolic as well as the arylic protons on the non-functionalized meso-substituents give
rise to two doublets each with characteristic couplings of 3 J = 4.8 Hz (β-pyrr.) and 3 J = 8.3 Hz
(arylic), respectively, which is completely in line with the D2h symmetry pattern. The signal
for the methylene group carrying the functionality is detected as a singlet at 3.29 ppm, i. e.
shifted upfield by 0.78 ppm compared to the o-bromomethyl substituted precursor
(4.07 ppm) analog to the other compound series under investigation. The t-butyl groups are
observed as two singlets in a 1 : 1 ratio at 1.67 and 1.63 ppm being also typical for that
substitution pattern. Finally, most upfield, the resonance for the inner ring amine protons is
found at -2.62 ppm.
N
NC
CN
NH
107