Copper naphthalocyanine

Analogously, the corresponding octa(phcnylsulfanyl)- (16 %), octa(phenylseianyl)- (51 %) and octa(phenyltellanyl)-substituted (35%) copper(II) 2,3-naphthalocyanines can be prepared. 

Photothermal sensitization has been mentioned briefly with regard to nickel(II) octabutoxy-naphthalocyanine (Section 9.22.10.1). A similar phenomenon has been observed with copper(II) haematoporphyrin ((1), Cu for 2H).196 This substance is accumulated by amelanotic melanoma cells. When the impregnated cells were subjected to light from a quartz-halogen lamp cell survival was not affected (i.e., no PDT effect), but intense pulsed laser irradiation (532 nm, Q-switched... 

The phthalocyanines, naphthalocyanines, and certain of their metal derivatives (Figure 6.17) are infrared fluorophores. 61"64 As a class, they are exceptionally stable compounds, with copper (Cu) phthalocyanine (not a fluorophore) remaining intact above 300 °C in air. First used for textile dyeing in the last century and still widely used, there is a rich chemistry of phthalocyanines. Most derivatives can be made by prolonged heating of a phthalimide or phthalic acid derivative with a metal in powder or salt form at elevated temperature. Several derivatives absorb in the near-IR, and either fluoresce or phosphoresce. The electronic transitions of phthalocyanines are complex and have been extensively studied, at least in part because the symmetry of the molecule makes theoretical calculations of its spectroscopic behavior more tractable. Unsubstituted phthalocyanines and naphthalocyanines are, as a class, very insoluble in solvents other than, for instance, nitrobenzene. Sulfonated phthalocyanines are water soluble and exhibit spectra comparable to the parent derivative. Photolumines-cent phthalocyanines (Pcs) include SiPc, ZnPc, and PC itself. These compounds have been little used for practical infrared fluorometry to date however, Diatron Corpora-... 

LB films of copper (II) octa-n-butoxy-2,3-naphthalocyanine show good sensitivities to vapor of alcohols, with the following sequence of sensitivities i-PrOH, EtOH, MeOH [64]. The response time and recovery time to vapor of MeOH, EtOH, and t-PrOH [volume fraction (1-5) x 10 ] were within 2 and 5 seconds, respectively, while those of the LB films to ammonia (1 x 10 " ) were 30-60 seconds and 4-5 minutes, respectively. 

Figure 14.29. RAIRS of the naphthalocyanine onto a smooth copper surface. Relative in-...

The adsorption of vanadyl-5,14, 23, 32-tetraphenyl-2, 3-naphthalocyanine VOTPNPc and vanadyl-5,10,15, 20-tetraphenyl-21H,31H-porphine VOTPPORP macrocycles onto metallic surfaces has been studied by Carrasco et al . A weak adsorbate-substrate interaction and no significant structural modifications imposed by surface effect were inferred from the IR spectra of the compounds deposited onto a KBr monocrystal and onto a smooth copper surface. 

The relative intensity ratio between selected bands measured in IRRAS suggested that in the case of the naphthalocyanine complex the compound is oriented with the naphthalocyanine moiety plane parallel to the copper surface the VO and the phenyl groups in both complexes are oriented perpendicular to the macrocycles rings, with the oxygen atom opposed to the metallic surface. Therefore, it exist a preferential molecular orientation of the molecules deposited onto the copper surface. 

The surface model was identical to that used in the case of a similar study carried out for azabipiridyl, naphthalocyanine (NPc) and CuNPc macrocycles interacting with a copper surface ... 

M. Saavedra, F. Mendizabal, M.M. Campos-Vallette, R.E. Clavijo, and G. Diaz (1998). Infrared and theoretical interpretation of the structure of naphthalocyanine and its copper(II) complex deposited onto a smooth copper surface. Vib. Spectrosc. 18, 25. 

Application of the same methods starting from 1,2-dicyanonaphthalene [11] yields 1,2-naphthalocyaninatometal complexes. The magnesium, lead, copper and zinc 1,2-naphthalocyanines (1,2-NcM) were first prepared by Linstead [12], Compared to the corresponding phthalocyanines the known 1,2-naphthalocyaninatometal compounds exhibit a higher thermal and chemical stability. When 1,2-NcM, is synthesized from 1,2-dicyanonaphthalene four different positional isomers are formed (compare to 2,3-NcM, Fig. 1) [11],... 

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