One-Pot Conversion of Fluorophores to Phosphorophores

The porphyrinoids shows quite significant chemical and photophysical properties.^1-3 Development of simple and efficient procedures for corrole synthesis, combined with facile tuning of physical and chemical characteristics by changing substituents on either the macrocycle or the chelate metal, has elevated in various extensive applications.^4,5

We have introduced a very efficient and facile one-pot conversion of free base 5,10,15-tris(pentafluorophenyl)corrole, (H₃)tpfc, into the coinage metal complexes of 2,3,17,18-tetraiodo-5-10-15-tris(pentafluorophenyl)corrole, (I₄-tpfc)M (M = Cu, Ag, Au). The iodoniation/metallation procedures provide much higher yields and larger selectivity than both conceivable stepwise syntheses. Photophysical analysis discloses that the gold(III) complex (I₄-tpfc)Au displays phosphorescence at room temperature and a substantial quantum yield for singlet oxygen formation. We trust the conclusions deduced from this research to be of large utility for structure/activity tuning of other corroles and related ligands. We are presenting now our results on the facile one-pot synthesis of group 11 metals with tetraiodinated-corroles, as well as some functionalization of the C-I bonds therein.⁶

References:

1. Lemon, C. M.; Brothers, P. J. Porphyrins Phthalocyanines 2011, 15, 809.
2. Flamigni, L. The Chemical Rec. 2016, 47, 32.
3. Sudhakar, K; Giribabu, L; D’Souza, F. etc. –An Asian J. 2015, 10, 2708.
4. Vestfrid, J.; Goldberg, I.; Gross, Z. Chem. 2014, 53, 10536.
5. Vestfrid, J.; Kothari, R.; Kostenko, A.; Goldberg, I.; Tumanskii, B.; Gross, Z. Chem. 2016, 55, 6061.
6. Soll, M.; Sudhakar, K.; Fridman, N; Müller, A; Röder, B.; Gross, Z. Org. Lett. 2016 in press.