II -porphyrin was recently obtained from fusing the β,β'-positions of the porphyrin core with four quinone units. Here, studies with metal-fre …">

Panchromatic π-Extended Porphyrins from Conjugation with Quinones - PubMed (original) (raw)

. 2016 May;81(5):477-488.

doi: 10.1002/cplu.201600115. Epub 2016 Apr 6.

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Panchromatic π-Extended Porphyrins from Conjugation with Quinones

Srinivas Banala et al. Chempluschem. 2016 May.

Abstract

Typical porphyrins are coloured compounds due to their characteristic wavelength-selective visible light absorptions. An exceptional "blackened" ZnII -porphyrin was recently obtained from fusing the β,β'-positions of the porphyrin core with four quinone units. Here, studies with metal-free and NiII -containing analogues are reported. These quinone-fused porphyrins were prepared from the corresponding β,β'-tetrasulfolenoporphyrins via thermally generated porphyrindienes, which were trapped by [4+2] cycloaddition as benzoquinone cycloadducts, which were subsequently oxidised. By using this strategy, metal-free and NiII -containing porphyrins with one, two, three or four conjugated naphthoquinone moieties were prepared efficiently. The presence of the π-conjugated naphthoquinone moieties changed the porphyrin chromophores profoundly, giving broadly absorbing "blackened" pigments. The influence of coordinated NiII ions, or of the absence of a metal ion in the modified porphyrin core, on their structural and spectroscopic properties was explored. Blackened quinone-conjugated porphyrins might be pigments suitable for solar energy conversion. With their unique peripheral functional groups they are also a set of porphyrins "programmed" for further covalent extension. Thus, they are building blocks for the preparation of supra-porphyrinoid assemblies that might be useful in optoelectronics and in the nanosciences.

Keywords: cycloaddition; naphthoquinones; porphyrinoids; solar energy; transition metals.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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