Soluble alkyl (II, 8a,b), fluoroalkyl (4a), and fluoroalkoxy (4b,c, 8c) 1,(4)- or 2,(3)-substituted phthalocyaninato- and linear 2,(3)- and angular 1,(2)-annulated naphthalocyaninatotitanium(IV) oxides 10, 12, and 14 were synthesized and characterized with regard to their spectroscopic, photophysical, and photochemical properties. While alkyl- and fluoroalkoxy-substituted compounds are highly soluble in nonpolar solvents, e.g., hexane, fluoroalkyl-substituted compounds are better soluble in polar aprotic solvents such as acetone. The stability against photooxidation in solution is enhanced on going from alkylated phthalocyanines 1,(4)-(C5H11)8PcTiO (8a), 1,(4)-(C6H13)8PcTiO (8b), and 2,(3)-(C4H9)8PcTiO (II) to fluorinated phthalocyanines 2,(3)-(CF3)4PcTiO (4a), 2,(3)-(CF3CH2O)4PcTiO (4b), and 2,(3)-(CF3CH2O)8PcTiO (4c), from phthalocyanines to naphthalocyanines (tert-butyl)4-2,(3)-NcTiO (10), 1,(2)-NcTiO (12), and (tert-butyl)4-1,(2)-NcTiO (14), and on going from 2,(3)-substituted 4a−c to 1,(4)-substitute...

Study of Substituent Effects on the Photoconductivity of Soluble 2,(3)- and 1,(4)-Substituted Phthalocyaninato- and Naphthalocyaninatotitanium(IV) Oxides

(1,2-Naphthalocyaninato)lutetium(III), bis(1,2-naphthalocyaninato)lutetium(III), and tris(1,2-naphthalocyaninato)dilutetium(III) have been synthesized in good yields. These complexes were characterized by UV−visible, 1H NMR, and mass spectroscopies and by electrochemical techniques. Bis(1,2-naphthalocyaninato)lutetium(III) is compared to bis(2,3-naphthalocyaninato)lutetium(III):  the good correspondance between the experimental data and theoretical results obtained by others is emphasized in this work. Stacking one to three macrocyclic rings is possible in the series of the 1,2-naphthalocyanine sandwich-like complexes with lutetium(III); as shown by UV−visible spectroelectrochemistry and voltammetry, this influences greatly the π-conjugated systems, modifying spectacularly their spectroscopic and redox properties.

From the Single- to the Triple-Decker Sandwich. Effect of Stacking on the Redox and UV-Visible Spectroscopic Properties of Lutetium(III) 1,2-Naphthalocyaninate Complexes.

Soluble alkyl‐ and alkoxy‐substituted titaniumoxo phthalocyanines: Synthesis and photoconductivity

We have prepared a series of 2,3-naphthalocyanine (H2NPc) compounds and examined their spectroscopic properties All of them can be vacuum sublimed as thin films which absorb strongly in the near i

E. F. Bradbrook

Papers

384. The preparation of the ten dicyanonaphthalenes and the related naphthalenedicarboxylic acids