@article {754,
	title = {Synthesis and characterization of beta-trifluoromethyl-meso-tetraphenylporphyrins},
	journal = {Journal of Organic Chemistry},
	volume = {68},
	number = {5},
	year = {2003},
	note = {ISI Document Delivery No.: 651PVTimes Cited: 18Cited Reference Count: 59},
	month = {Mar},
	pages = {1892-1900},
	type = {Article},
	abstract = {beta-Trifluoromethyl-meso-tetraphenylporphyrins were synthesized to investigate the electronic and steric effects of the trifluoromethyl groups on the macrocycle. Preparation of these novel porphyrins was carried out by copper-assisted trifluoromethylation of beta-tetrabromo-meso-tetraphenylporphyrin metal complexes and in situ generated CF3Cu. For comparison, the beta-methyl analogues were also prepared. Analysis of beta-trifluoromethylporphyrins by UV-vis, NMR, and cyclic voltammetry (CV) showed that the electron-withdrawing effects of the trifluoromethyl groups on the antipodal pyrroles required the macrocycle to take a fixed 18pi-electron pathway. UV-vis, CV, and molecular modeling studies suggest that the novel porphyrins are distorted following introduction of trifluoromethyl groups onto the pyrrolic beta-position of meso-tetraphenylporphyrin. The pK(a) difference of beta-tetrakis(trifluoromethyl)-meso-tetraphenylporphyrin from that of DBU in CH2Cl2, obtained by spectrophotometric titration, affirms that it is one of the most electron-deficient porphyrins so far prepared.},
	keywords = {BROMINATED-PYRROLE TETRAPHENYLPORPHYRIN, COMPLEXES, EFFICIENT CATALYSTS, ELECTROCHEMISTRY, ELECTRON-DEFICIENT PORPHYRINS, HYDROXYLATION, METALLOPORPHYRINS, REDOX POTENTIALS, SUBSTITUENTS, X VARIES},
	isbn = {0022-3263},
	url = {<Go to ISI>://000181329900033},
	author = {Terazono, Y. and Dolphin, D.}
}
