116453-89-5Relevant articles and documents
Photochromic reactions involving palladium(II) octabutoxynaphthalocyanine and molecular oxygen
Rihter, Boris D.,Kenney, Malcolm E.,Ford, William E.,Rodgers, Michael A. J.
, p. 8146 - 8152 (1993)
The palladium complex of 1,6,10,15,19,24,28,33-octabutoxynaphthalocyanine, PdNc(OBu)8, is shown to undergo reversible addition of O2 in benzene solution at ambient temperature (22 ± 1 °C) during steady-state photolysis with an Ar ion laser. On the basis of 1H-NMR and electronic absorption spectral evidence, the photoadduct is postulated to be an endoperoxide which has molecular oxygen added to one of the benzene rings at the sites α to the point of fusion with the tetrapyrrole ring, i.e., the positions bearing butoxy substituents. The formation of this product probably involves O2(1Δg). The photoadduct decomposes mainly back into PdNc(OBu)8 by a thermal process whose first-order rate constant is (2.6 ± 0.2) × 10-4 s-1 at 22 °C. This reaction is accelerated by light. Laser flash photolysis results show that the quantum efficiency for the formation of the photoadduct in O2-saturated benzene is 8 in Ar-saturated benzene is 0.035 ± 0.010 with either 355-or 532-nm light, but the value is 0.0015 ± 0.0005 with 683-nm light. PdNc(OBu)8 may be the first example of a tetrapyrrole to form a metastable endoperoxide, and the latter compound appears to be the first example of an endoperoxide that is subject to photocycloreversion with visible light. It is also demonstrated that energy transfer from O2(1Δg) to PdNc(OBu)8 occurs with a bimolecular rate constant of9 × 109 M-1 s-1 to produce PdNc(OBu)8(T1) which phosphoresces in fluid solution. This behavior suggests that the platinum group metal complexes of octaalkoxynaphthalocyanine may prove to be useful as luminescence probes for improving the detection limit of O2(1Δg).
Synthesis of a novel asymmetrical octasubstituted zinc naphthalocyanine
Qiu,Cheng,Wu
, p. 52 - 53 (2007/10/03)
The synthesis and characterization of a novel asymmetrical octasubstituted zinc naphthalocyanine 〈ZnNc〈OR1〉6〈OR2〉 2, R1=C4H9, R2=CH2CH2OCH3〉 made by mixed condensation are described.
Octa-alkoxy Phthalocyanine and Naphthalocyanine Derivatives: Dyes with Q-band Absorption in the Far Red or Near Infrared
Cook, Michael J.,Dunn, Adrian J.,Howe, Steven D.,Thomson, Andrew J.,Harrison, Kenneth J.
, p. 2453 - 2458 (2007/10/02)
The lithium alkoxide-catalysed cyclic tetramerisation of various 3,6-dialkoxy-4,5-dichlorophthalonitriles, 1,4-dialkoxynaphthalene-2,3-dicarbonitriles and 3,6-dialkoxyphthalonitriles to give the corresponding metal-free octa-alkoxyoctachlorophthalocyanines, octa-alkoxynaphthalocyanines and octa-alkoxyphthalocyanines is described.An unexpected trans-alkoxylation reaction occurs during the cyclisation of the first two series of precursors.Metal-free phthalocyanines and naphthalocyanines have been converted into derivatives containing various metal ions.Compounds show Q-band absorption in the region 739-862 nm in toluene solution.The fluorescence spectra of selected examples are reported.The solubility of some of the compounds has been measured in a formulation of liquid crystal materials.
