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

Abstract

The regioselective preparation of ortho‐substituted subphthalocyanides was achieved employing 3‐substituted phthalonitrile derivatives as starting materials. A mechanistic proposal has been outlined.

An optically-active subphthalocyanine dimer

“…Monosubstituted phthalonitriles produce racemic mixtures of a pair of regioisomeric SubPcs with C 3 and C 1 symmetry. [7][8][9][10][11] The separation of both the SubPc regioisomers and, using a chiral HPLC column, the enantiomeric forms, have been reported by Claessens and Torres. 9 Kobayashi et al 11 have published a circular dichroism study of SubPcs with C 3 symmetry.…”

The influence of strong and weak hydrogen bonds on the solid state arrangement of hydroxy-containing boron subphthalocyanines

“…1), thus permitting the modification of physical and spectral properties in a controlled fashion. [4][5][6][7][8][9][10][11][12][13][14] Recently, BsubPcs have attracted attention because of their interesting optical and electronic properties, and are being investigated for applications such as organic field effect transistors (OTFTs), organic light emitting diodes (OLEDs), and organic solar cells (OSCs). 15 BsubPc derivatives are typically employed in the solid state in organic electronic applications, and some correlation between solid state packing parameters and charge carrier mobility has been demonstrated in vacuum-deposited BsubPc films.…”

Phthalocyanine Nano Colloids in Water Prepared by Reprecipitation Method

“…1,2-Dicyano-4-iso-amylsulfinylbenzene 5 and 1,2-dicyano-4-iso-amylsulfonylbenzene 6 were synthesized in accordance with modified literature procedures. 9,10,11,12,13,14,15 The four substituted phthalocyanines were mixtures of the four corresponding regioisomers. Therefore, they were characterized without further isolation from their FT/IR spectra and HRMS.…”