A Convenient Synthetic Method for Pure Oxo(phthalocyaninato)titanium(IV) and Application to Other Metal Phthalocyanines

Abstract

High-yield synthesis of pure oxo(phthalocyaninato)titanium(IV) was conveniently achieved by heating a mixture of 1,2-dicyanobenzene, titanium(IV) butoxide, urea, and 1-octanol at 150 °C. It is suggested that a key pathway of the efficient condensation reaction is the complex formation of titanium(IV) butoxide with ammonia generated by the nucleophilic attack of 1-octanol to urea. Applicabilities of this method were investigated for condensation reactions of 1,2-dicyanobenzene with other metal alkoxides.

Synthesis and X-ray crystal structures of imido and ureato derivatives of titanium(iv) phthalocyanine and their application in the catalytic formation of carbodiimides by metathesis from isocyanates

“…The IR spectra of all TiPc's show the typical absorptions of the basic Pc moiety, such as n C C at 1608 cm -1 , while the characteristic Ti O stretching band (n Ti O at 965 cm -1 ) is not observed. 31 Additionally, the vibrations at 1683 cm -1 (3a) and 1684 cm -1 (3b) can be assigned to the carbonyl group (n C O ). 24 UV/vis spectra of 1, 2a and 3a (Fig.…”

Synthesis, Characterization, and Photovoltaic Properties of Soluble TiOPc Derivatives

“…The TiOPc derivatives, 2,9,16,23-tridecyloxyphthalocyaninato oxotitanium(IV) ( 3a) and 2,9,16,23-pentadecyloxyphthalocyaninato oxotitanium(IV) ( 3b) were prepared using the two-step synthesis described in Ref. [ 23 ]. The synthetic route of TiOPc derivatives is shown in Scheme 1.…”

Convenient synthesis of phthalocyanines with disilazanes under mild conditions

“…Urea is used in the production of phthalocyanines from less expensive starting materials such as phthalic acids, phthalic anhydrides and phthalimides but the reaction needs severe conditions which often cause the formation of undesirable by-products. 9 Recently, we have reported that hexamethyldisilazane 10 (HMDS) is an excellent reagent for the construction of the phthalocyanine framework from phthalimides, phthalic anhydrides, and phthalonitriles. 11 Various metallophthalocyanines can be prepared under mild conditions on heating with HMDS.…”