| To solve the problem associated with poor solubility of phthalocyanines and easy aggregation,the first example of introduce the positively charge bis-quaternary ammonium compounds with methyl pyridine and isoquinoline terminal groups were introduced into the peripheral positions of silicon(IV)phthalocyanines.On the one hand,it can endowed the water solubility of phthalocyanines in favour of the incorporation of negative drug-resistant bacteria.On the other hand,it can inhibite the formation of aggregation through the vast space steric hindrance of ary type structure.In this paper,a novel series of hydrophobicity and hydrophily arm-type silicon(IV)phthalocyanines have been synthesized.They were bis-(3,5-bis-(bromopropoxy))benzyloxy/bis-(3,5-bis-(bromobutoxy))benzyloxy axially substituted silicon(IV)phthalocyanine(MlSiPc/M2SiPc),bis-(3,5-bis-(1’,3’-methylpyridine bromopropoxy)benzyloxy))silicon(IV)phthalocyanine(NISiPc),bis-(3,5-bis-(1’,4’-isoquinoline bromopropoxy)benzyloxy))silicon(IV)phthalocyanine(N2SiPc),bis-(3,5-bis-(1’,3’-methylpyridine bromobutoxy)benzyloxy))silicon(IV)phthalocyanine(N3SiPc),bis-(3,5-bis-(1’,4’-isoquinoline bromobutoxy)benzyloxy))silicon(IV)phthalocyanine(N4SiPc).The structures of these phthalocyanines were characterized by IR,1HNMR,ESI-MS and MALDI-TOF-MS methods.The photophysical properties of hydrophobicity and hydrophily arm-type cationic silicon(IV)phthalocyanines were studied by UV/Vis,steady-state and time-resolved fluorescence spectroscopic methods.The results indicated that hydrophobicity and hydrophily silicon(IV)phthalocyanines(MISiPc,M2SiPc,N1SiPc,N2SiPc,N3SiPc and N4SiPc)were dissolved existed mainly as monomer in DMF solvents.Length of branch exerted no significant effect on the maximum absorption peak position and intensity for the Q band of M1SiPc and M2SiPc.Because of the solvent polarity,maximum Q-band of water-soluble phthalocyanines has a marked redshifted compared that in the aqueous solution.Also,fluorescence intensity,the fluorescence quantum yield and singlet oxygen quantum yield of water-soluble phthalocyanines were significantly weaker than those in DMF,which mainly due to the to easily aggregation in aqueous solution.What’s more,the singlet oxygen quantum yields of methylpyridine substituented phthalocyanines higher than that of with isoquinoline substitution.The photodynamic antimicrobial chemotherapy of water-soluble arm-type phthalocyanines for acinetobacter baumannii were studied.Acinetobacter baumannii could be selectively uptake by water-soluble arm-type silicon phthalocyanine bearing different substituent groups.The uptake amount of methyl pyridine substituented silicon phthalocyanine reached largest at 12 h.Better antimicrobial result was obtained.This might because that the surface positive charge of phthalocyanine can easily combined with negative bacteria and produce singlet oxygen quantum to kill them.Wrapped CTAB gold nanorods(GNRs)are prepared by the seed-mediated method.The water-soluble phthalocyanines nanoparticlescomposite were prepared by layer-by-layer self-assembly cationic water-insoluble arm-type silicon(Ⅳ)phthalocyanines(NlSiPc/N2SiPc)to the negative charge polyelectrolyte(PSS)electrostaticallyencapsulated the polyelectrolyte-coated gold nanorods surface.To reduce the toxicity of perpheral CTAB of gold nanorods,polyelectrolyte and water-soluble phthalocyanines were layer-by-layer self-assembled.The UV/Vis absorption spectra showed that the longitudinally localized surface plasmon resonance(LSPR)peak exhibited red-shifted,weaking of the intensity and widening of the peak shape,which indicated that the capacity of phthalocyanine increased.TEM images of water-soluble phthalocyanines composite nanoparticles showed rod morphology.The Zeta potential measurements showed evidence for bulk average successful polymer layer coating,as the nanorod surface charge changed in accord with the net charge of each assemble layer.Irradiated by laser(688nm,500mW/cm2),the gold nanorods absorb light energy and converted into heat,showed that water-soluble phthalocyanines@gold nanorods composite has obvious heat effect that the system of temperature rise over time.The result is that induced the release of phthalocyanine(N1SiPc/N2SiP)from the composite nanoparticles,however liberaterd scarcely any without laser irradiation.All in all,light activated control the release of water-soluble arm-type phthalocyanine.This result will provide some data for the self-assemble and control release of nano-based photosensitizer. |
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