Subphthalocyanine-based porous organic polymers

Abstract

The synthesis and photophysical properties of two subphthalocyanine-based porous organic polymers (SubPc-POPs) are reported.

Recent advances in subphthalocyanines and related subporphyrinoids

“…Axial substitution of the axial chlorine atom with phenols is commonly carried out by refluxing the starting SubPc-Cl with the corresponding alcohol in a high-boiling point aromatic solvent such as toluene, 46–48,50,53–56,58,70,73,76,91–117 1 : 1 toluene/THF mixture, 118 chlorobenzene, 17,119 dichlorobenzene (DCB) 29,30 and o -xylene. 120 Interestingly, reaction of SubPc-Cl, SubPc-Br and mesylated SubPcs with phenols in DMF was found to afford the corresponding formate derivative in addition to the target phenoxy conjugate and the hydrolyzed SubPc-OH product ( vide infra ). 121 Axial substitution with phenols can be performed by a one-pot two-step procedure without purification of the chlorinated precursor, by adding the aryl alcohol and the solvent directly to the crude cyclotrimerization product.…”

“…Deprotection of silyl ether groups in the presence of CsF in acetone and subsequent reaction of the hydroxy-substituted SubPc with 1,4-benzene diboronic acid have also been reported. 120…”

“…It was based on the reaction between hexahydroxy-SubPc and 1,4-benzene diboronic acid in a 1 : 1 (v/v) mixture of dioxane and mesitylene at 105 °C for three days. 120 Both the choice of the reaction solvent, temperature and the substitution of the axial chlorine atom by a phenoxy substituent were crucial factors for the success of this process. The POP-SubPc derivatives 162 and 163 were characterized by different techniques.…”

Fluorous phthalocyanines and subphthalocyanines

“…The synthesis of F-SubPCs, as shown in Scheme 2, was accomplished by adapting previous literature procedures [23]. In brief, the phthalonitrile precursors 1-3 were prepared by an SNAr reaction of the fluoroalkyl thiols and halogenated phthalonitriles.…”

Electronic Structure, Bonding, and Stability of Boron Subphthalocyanine Halides and Pseudohalides

“…[12] This work clarified that BsubPc is an aromatic macrocycle with resonance, as isoindoline and imide bonds around the boron complex are equally distributed in the solid state. Interestingly, it was later found that BsubPc-based linear [13][14][15] and porous [16,17] polymeric materials can be formed. Years later, the lack of systematic BsubPc structural analysis prompted Virdo et al to reconfirm the solid-state structure and examine its possible dependence on several variables.…”