Subphthalocyanines: Preparation, Reactivity and Physical Properties

Synthesis and structure of the coordinatively unsaturated boron subphthalocyanine cation, [B(SubPc)]+

“…Protonation of the bridging O atom in -oxo iron(III) porphyrin dimers is known [27,28], so the present result reflects the basicity of the aza bridge N atoms in the subPc macrocycle relative to the bridge O atom. The neutral -oxo dimer (t-BuSubPc)B-O-B(t-BuSubPc) has been previously isolated [7,29]. The structure of the cation in 3 is shown in Fig.…”

A New Substitution Pattern in Subphthalocyanines: Regioselective Synthesis and Separation of “ortho” Derivatives

“…Subphthalocyanines [1] (SubPcs, a and b in Figure 1) are cone-shaped [2] macrocycles comprising three N-fused diiminoisoindoline units around a boron core. Their particular structure and their 14 π-electron extended aromatic [3] ring make them ideal candidates for a study of their second order nonlinear optical (NLO) properties, [4] their potential use in PhotoDynamic Therapy, [4e] and for the preparation of Langmuir-Blodgett films.…”

“…[1][2][3][4] Trisubstituted SubPcs (one group in each isoindole subunit) have been isolated as 3:1 mixtures of constitutional isomers with C 1 and C 3 symmetries, that could be resolved only in one case by HPLC.…”

“…This substitution pattern renders the C 1 and C 3 constitutional isomers of the axially substituted chlorosubphthalocyanines structurally different enough from each other to make possible, for the first time, their easy separation by column chromatography. [1] For the sake of consistency with former work in our laboratory, and also for [2d] and (e) phenyl-boronsubphthalocyanine chemical compatibility reasons with BCl 3 , we chose as substituents for this study the groups NO 2 , I, SC 3 H 7 , and SO 2 C 3 H 7 . By studying the regioselectivity of the processes leading to the formation of the SubPcs we have been able to outline a mechanistic proposal based on steric factors.…”

Synthesis of a Monofunctional Phthalocyanine on Silica

“…For this purpose it is a prospective approach to bind a phthalocyanine bearing only one reactive substituent without crosslinking at suitable carriers like organic polymers, inorganic high molecular weight compounds or monoclonal antibodies. Monofunctional phthalocyanines are prepared by statistical synthesis employing two different dicarbonitriles [6][7][8][9], ring opening of a so-called subphthalocyanine in the presence of a differently substituted dicarbonitrile [10][11][12][13] or reaction of a polymer-bonded dicarbonitrile with differently substituted dicarbonitriles in solution followed by cleavage of the formed phthalocyanine [14][15][16]. Every method exhibits advantages and disadvantages which will not be discussed here.…”