meso-tetraalkynylporphyrins

Journal article

5,10,15,20-Tetra(4-n-butylphenylethynyl)porphyrin has been synthesised from 4-n-butylphenylpropynal and converted into its zinc(II) and lead(II) complexes. The solution electronic spectra of these porphyrins are compared to the analogous complexes of 5,10,15,20-tetra(trimethylsilylethynyl)porphyrin. The aryl rings of the tetra(4-n-butylphenylethynyl)porphyrin extend the porphyrin chromophore, resulting in an increase in the oscillator strength and a bathochromic shift of about 600 cm-1 in all the absorption bands. Metallation with lead(II) results in a larger bathochromic shift of about 1400 cm-1, when compared with zinc(II). The crystal structure of the pyridine zinc complex of 5,10,15,20-tetra(4-butylphenylethynyl)-porphyrin shows that the molecule has a large approximately planar π-system. Pairs of diagonally off-set π-π stacked porphyrins pack into a layer structure. Each pyridine ligand is located in a pocket defined by four butyl chains.

Authors: Anderson, H; Wylie, A; Prout, K

• Publication status: Published
• Journal: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
• Issue: 10
• Pages: 1607-1611
• Publication date: 1998-05-21
• DOI: 10.1039/a800992i
• EISSN: 1364-5463
• ISSN: 0300-922X
• Language: English