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Issue 5, 2009
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Synthesis and phase behaviour of β-octaalkyl porphyrins

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A homologous series of three octakis-alkyl-substituted porphyrin (OAP) derivatives with alkyl chain lengths of C8, C10 and C12 has been synthesised. For each compound, both the free-base (i.e. two H-atoms) and the fourfold coordinated zinc complex were investigated, where the latter for each chain length was found to exhibit liquid-crystalline mesophase behaviour. At low temperatures all three metal coordinated compounds formed a solid S phase with a structure based on a square packing of columns with a stacking periodicity of approx. 4.5 Å. At increased temperatures the square packed solid S phases undergo phase transitions to liquid-crystalline columnar phases based on centred rectangular lattices of C2/m symmetry, with the ratio of the lattice parameters, a/b, ranging between 1 and 1.732. The a/b ratio exhibited two discontinuous jumps with increasing temperature prior to melting to the isotropic phase for Zn-OAP-C8, implying the existence of three columnar phases denoted Colr1, Colr2 and Colr3. For the longer chain length compounds, the number of mesophases formed was reduced, first to two for Zn-OAP-C10, then to one for Zn-OAP-C12.

Graphical abstract: Synthesis and phase behaviour of β-octaalkyl porphyrins

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The article was received on 24 Jul 2008, accepted on 17 Oct 2008 and first published on 20 Nov 2008

Article type: Paper
DOI: 10.1039/B812724G
J. Mater. Chem., 2009,19, 598-604

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    Synthesis and phase behaviour of β-octaalkyl porphyrins

    G. C. Shearman, G. Yahioglu, J. Kirstein, L. R. Milgrom and J. M. Seddon, J. Mater. Chem., 2009, 19, 598
    DOI: 10.1039/B812724G

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