Synthesis of three asymmetric N-confused tetraarylporphyrins.
Two monosubstituted and one tetrasubstituted N-confused porphyrins (1-3) were prepared in ca. 3-5% yields using a [2 + 2] synthesis. The monosubstituted porphyrins have carbomethoxy (1) or nitro (2) substituents on one of the meso-phenyl groups, while the meso-phenyl groups of the third NCP (3) are substituted with nitro, bromo, and methyl groups in an AB(2)C pattern. The specific regiochemistry of the aryl rings around the macrocycle in each porphyrin was definitively determined using a combination of 1D ((1)H and (13)C) and 2D (gHMBC, gHSQC and ROESY) NMR spectroscopy. The absorption spectra of 1-3 in CH(2)Cl(2) are similar to those of N-confused tetraphenylporphyrin (NCTPP) but have Soret and Q bands that are shifted to lower energies with smaller extinction coefficients in comparison to those for NCTPP.
Department of Chemistry, Knight Chemical Laboratory, The University of Akron, Akron, Ohio 44325-3601, USA.
Rajendra
R
Acharya
Liladhar
L
Paudel
Jojo
J
Joseph
Claire E
CE
McCarthy
Venkat R
VR
Dudipala
Jody M
JM
Modarelli
David A
DA
Modarelli
D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet
D011166:Porphyrins