Synthesis and spectroscopy of a series of substituted N-confused tetraphenylporphyrins.
A series of N-confused tetraphenylporphyrins (H(2)NCTPPs) with substituents on either the para- or the 3,5-positions of the meso phenyl rings were prepared using Lindsey conditions. Both electron-withdrawing and electron-donating groups were chosen in order to probe the effects of peripheral substitution on the properties of the macrocycles. The series includes 5,10,15,20-tetra-(4-R-phenyl) N-confused porphyrins (where R = bromo (1), iodo (2), cyano (3), methoxy (4), 2',5'-dimethoxyphenyl (5), or ethynyl (6)) and 5,10,15,20-(3,5-di-tert-butylphenyl) N-confused porphyrin (7). Absorption and steady-state fluorescence measurements were carried out, and quantum yields were measured for all compounds in both dichloromethane (CH(2)Cl(2)) and dimethylacetamide (DMAc).
Shaw
Janet L
JL
Department of Chemistry, Knight Chemical Laboratory, The University of Akron, Akron, Ohio 44325-3601, USA.
Garrison
Shana A
SA
Alemán
Elvin A
EA
Ziegler
Christopher J
CJ
Modarelli
David A
DA