Zinc naphthalocyanine

Zinc naphthalocyanine has been prepared in low yield (18%) by the template reaction of Zn(02CMe)2, urea and 2,3-naphthalenedicarboxylic acid.1138 The synthesis of zinc tetra-2,3-naphthoporphine by a template reaction has been described.1139... 

Photoinduced Electron Transfer in a Self-assembled Zinc Naphthalocyanine-Fullerene Diad... 

The self-assembled diad formed by axial coordination of zinc naphthalocyanine (ZnNc) and fulleropyrrolidine bearing a coordinating imidazole ligand (Qolm) is a good example of a supramolecular system undergoing photoinduced electron... 

Scheme 7.3. Structure of the zinc naphthalocyanine-fullerene diad (ZnNc). (Reprinted with permission from ref. [20]).

Zinc hydrides, 931 Zinc naphthalocyanine preparation, 993 Zinc pseudohalides, 981 solid state, 985 Zirconium phosphate ion exchange resins, 720... 

Thitta R, Sandanayaka ASD, Schumacher AL, D Souza L, Araki Y, Ito O, D Souza F (2007) Donor—acceptor nanohybrids of zinc naphthalocyanine or zinc porphyrin noncovalently linked to single-wall carbcm nanotubes for photoinduced electron transfer. J Phys Chem C 111 6947-6955... 

Yanagi, H., T. Kouzeki, M. Ashida, T. Noguchi, A. Manivannan, K. Hashimoto, and A. Fujishima (1992). Molecular orientation of vacuum-deposited thin films of zinc-naphthalocyanine. LAppl. Phys. 71, 5146. 

Figure 13 Tetra-terr-butyl zinc naphthalocyanine 14. Imidazole and pyridine functionalized Cgo fullerenes 15-18.

Single wall nanotubes (SWNTs) have been employed as building blocks for PET systems in combination with naphthalocyanine 19 (Figure 14). In the first instance, SWNTs were solubilized by n-n stacking with a pyrene-fimctionalized imidazole moiety 20. In the second step, zinc naphthalocyanine 19 was axially coordinated to the... 

Figure 14 Supramolecular nanostructure formed between zinc naphthalocyanine 19, imidazole-fnnctionalized pyrene 20, and a single wall carbon nanotnbe.

Ring systems intermediate between phthalocyanines and naphthalocyanines are known 263,264 (51) is such a compound. They are most simply called benzonaphthoporphyrazines, and various zinc(II) complexes with cationic (A--m e t hy 1 pyridini um-3-oxy) substituents have Amax in the range 680-750 nm in solution or in Cremophor micelles, and show promise in bioassays in vivo.264... 

Early experiments with zinc(II) (and aluminum(III)) naphthalocyanine were not very promising, although the lower sulfonic acids did show some PDT activity.268,269 The chromophore is of... 

The absorption spectra of the silicon(IV) naphthalocyanines follows the pattern already seen with the analogous zinc(II) (Section 9.22.12.1.4) and aluminum(III) (Section 9.22.13.2) derivatives 354 the red band is shifted about 100 nm further to the red, with intensification. Bis(trihex-ylsiloxy)silicon(IV) naphthalocyanine has Amax(PhH) = 776 nm (e = 650,000 M-1 cm-1) and <1>A 0.35 (oxygen-saturated benzene).389 The solution is fluorescent (main emission at 780 nm, Tf 2.85 ns) the triplet energy (ca. 22 k cal mol-1) is a little less than the energy of the first singlet state of dioxygen, and the process (Equation (9)) is reversible (cf. compounds (40) and (41), Section 9.22.10.2). 

At the first stage of the research, several zinc(II) tetrapyrroles (porphyrin, phthalocyanine and naphthalocyanine derivatives) were investigated [27] in the systems containing sacrificed compounds. The results obtained contributed to the development of the theory of redox reactions and energy-transfer processes, they were, however, of little practical significance. 

Similarly, the pyridyl fullerenes 30 and 31 also axially bind to ZnNcCBu)4 (28) to form supramolecular triads in which the zinc(II) naphthalocyanine acts as an electron donor, the pyridyl fullerenes act as primary electron acceptors, and either the ferrocene (Fc) or iV,iV-dimethylaminophenyl (DMA) moiety serves as a second electron donor [43], Fig. 2 shows the optimized structures of the resulting triads calculated by density functional theory (DFT), showing that the three components are arranged in a linear fashion. The binding constants of these systems (7.4 x 104M 1 for [ZnNc( Bu)4] 30 and 10.2 x 104M 1 for [ZnNc( Bu)4] 31 in o-dichlorobenzene) determined by UV-Vis spectroscopy are comparable with... 

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],... 

---