Synthesis of a tricationic subphthalocyanine with potential use in photoinactivation of bacteria.

M. B. SPESIA, E. N. DURANTINI

http://www.mdpi.net/ecsoc-10. Molecular Diversity Preservation International (MDPI), Basel, Switzerland.

Conferencia; Tenth International Electronic Conference on Synthetic Organic Chemistry (ECSOC-10); 2006

Molecular Diversity Preservation International (MDPI), Basel, Switzerland.

A novel chloro[2,9,16(2,9,17)-trikis-4-(N-methylpyridyloxy)] subphthalocyaninnato boron(III) iodide (SubOPc3+) has been synthesized by boron trichloride-induced cyclotrimerization of 4-(4-pyridyloxy)phthalonitrile in 1-chloronaphthalene. This approach produced a regioisomers mixture of chloro[2,9,16(2,9,17)-trikis-4-(pyridyloxy)]subphthalocyaninnato boron(III) (SubOPc) with 19% yield. Exhaustive methylation of SubOPc with methyl iodide yielded 92% of tricationic SubOPc3+. The spectroscopic and photodynamic properties of the SubOPc3+ were compared with its homologous non-charged SubOPc and with subphthalocyanine (SubPc). The cationic SubOPc3+ is essentially aggregated in solution of different solvents and it is partially dissolved as monomer in N,N-dimethylformamide (DMF)/water (10% v/v)/HCl (1.2 mM). The singlet molecular oxygen, O2(1Dg), production was evaluated using 9,10-dimethylanthracene (DMA). The photodynamic effect was strongly dependent of the medium, diminishing where the sensitizer is aggregated but it increases in an appropriated surrounding microenvironment. The studies show that SubOPc3+ can be an interesting agent with potential applications in photodynamic inactivation of bacteria.