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Issue 1, 2011
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Structural characteristics that make chlorophylls green: interplay of hydrocarbon skeleton and substituents

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Abstract

Understanding the effects of substituents on natural photosynthetic pigments is essential for gaining a deep understanding of why such pigments were selected over the course of evolution for use in photosynthetic systems. This knowledge should provide for a more thoughtful design of artificial light-harvesting systems. The hydrocarbon skeleton of all chlorophylls is phorbine, which contains an annulated five-membered (isocyclic) ring in addition to the reduced pyrrole ring characteristic of chlorins. A phorbine and a 131-oxophorbine (which bears an oxo group in the isocyclic ring) were synthesized as benchmark molecules for fundamental spectral and photophysical studies. The phorbine and 131-oxophorbine macrocycles lack peripheral substituents other than a geminal dimethyl group in the reduced ring to stabilize the chlorin chromophore. The spectral properties and electronic structure of the zinc or free base 131-oxophorbine closely resemble those of the corresponding analogues of chlorophyll a. Accordingly, the fundamental electronic properties of chlorophylls are primarily a consequence of the 131-oxophorbine base macrocycle.

Graphical abstract: Structural characteristics that make chlorophylls green: interplay of hydrocarbon skeleton and substituents

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Publication details

The article was received on 21 Aug 2010, accepted on 06 Oct 2010 and first published on 10 Nov 2010


Article type: Paper
DOI: 10.1039/C0NJ00652A
Citation: New J. Chem., 2011,35, 76-88
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    Structural characteristics that make chlorophylls green: interplay of hydrocarbon skeleton and substituents

    O. Mass, M. Taniguchi, M. Ptaszek, J. W. Springer, K. M. Faries, J. R. Diers, D. F. Bocian, D. Holten and J. S. Lindsey, New J. Chem., 2011, 35, 76
    DOI: 10.1039/C0NJ00652A

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