Phthalocyanines bicyclic

Indium phthalocyanine (PcInCl) can be prepared by treating indium(III) chloride with phthalonitrile in a high-boiling solvent like quinoline139 or 1-chloronaphthalene.143 Dimeric indium(III) phthalocyanine complexes of the type Pc2In,144 Pc3In2145 as well as a bicyclic phthalocyanine (Pc3/2ln)146 are also known. 

Thallium phthalocyanine (PcT12) can be obtained by heating phthalonitrile with an inter-metallic alloy of indium and thallium in an evacuated glass ampule.145 The structure of this compound is unique among metal phthalocyanines as the two thallium cations occupy two opposite corners of an octahedron, which is formed by the thallium cations and the four iso-indolinc nitrogen atoms facing the center of the macrocycle.147 Another unusual type of phthalocyanine can be prepared by heating phthalonitrile with thallium metal.148 It was identified as a bicyclic thallium(III) phthalocyanine (Pc3/2T1).14S... 

Bicyclic phthalocyanines possess an unusual skeleton built from three halves of a normal phthalocyanine macrocycle, arranged like a propeller. Such compounds are formed by treating phthalonitrile at low pressure and high temperature (0.1 atm, N2,210 C, 1-2 d) in the presence of thallium148 or indium (yield 5%).146... 

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