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Issue 12, 2015
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Regiospecific synthesis of tetrasubstituted phthalocyanines and their liquid crystalline order

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Abstract

Metal-free and metal(II) all-endo-tetraalkoxy-phthalocyanines of C4h symmetry are synthesised regiospecifically from 3-(2-butyloctyloxy)phthalonitrile with lithium octanolate and subsequent metal ion exchange. The voluminous, yet not overly large, and racemically disordered alkoxy substituent not only renders the cyclotetramerisation regiospecific, but also leads to liquid crystalline self-assembly with attainable clearing temperatures and persisting columnar organisation at room temperature. A rare hexagonal mesophase with twelve columns per hexagonal unit cell is found in the metal-free homologue, whereas the metal complexes show rectangular mesophases. The clearing temperature increases with increasing axial component of the metal ion coordination sphere. At low temperature, significant antiferromagnetic exchange between magnetic centres is observed for the CoII homologue, whereas the magnetic centres are magnetically independent in the CuII derivative, in line with the observed higher clearing temperature in the CoII case that testifies of stronger interdisk interactions.

Graphical abstract: Regiospecific synthesis of tetrasubstituted phthalocyanines and their liquid crystalline order

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Article information


Submitted
08 Jan 2015
Accepted
09 Feb 2015
First published
09 Feb 2015

This article is Open Access

Dalton Trans., 2015,44, 5569-5576
Article type
Paper

Regiospecific synthesis of tetrasubstituted phthalocyanines and their liquid crystalline order

P. Apostol, A. Bentaleb, M. Rajaoarivelo, R. Clérac and H. Bock, Dalton Trans., 2015, 44, 5569
DOI: 10.1039/C5DT00076A

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