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Molecules 2014, 19(10), 15938-15954; doi:10.3390/molecules191015938

Lessons from Chlorophylls: Modifications of Porphyrinoids Towards Optimized Solar Energy Conversion

1
Faculty of Biochemistry, Biophysics and Biotechnology, Jagiellonian University, Gronostajowa 7, 30-387 Kraków, Poland
2
Chełkowski Institute of Physics, University of Silesia, Uniwersytecka 4, 40-007 Katowice, Poland
3
Department of Biophysics, University of Life Sciences in Lublin, Akademicka 13, 20-950 Lublin, Poland
4
Institute of Pharmacology, Polish Academy of Sciences, Smętna 12, 31-343 Kraków, Poland
*
Author to whom correspondence should be addressed.
Received: 21 April 2014 / Revised: 20 August 2014 / Accepted: 5 September 2014 / Published: 3 October 2014
(This article belongs to the Special Issue Macrocyclic Chemistry)
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Abstract

Practical applications of photosynthesis-inspired processes depend on a thorough understanding of the structures and physiochemical features of pigment molecules such as chlorophylls and bacteriochlorophylls. Consequently, the major structural features of these pigments have been systematically examined as to how they influence the S1 state energy, lifetimes, quantum yields, and pigment photostability. In particular, the effects of the macrocyclic π-electron system, central metal ion (CMI), peripheral substituents, and pigment aggregation, on these critical parameters are discussed. The results obtained confirm that the π-electron system of the chromophore has the greatest influence on the light energy conversion capacity of porphyrinoids. Its modifications lead to changes in molecular symmetry, which determine the energy levels of frontier orbitals and hence affect the S1 state properties. In the case of bacteriochlorophylls aggregation can also strongly decrease the S1 energy. The CMI may be considered as another influential structural feature which only moderately influences the ground-state properties of bacteriochlorophylls but strongly affects the singlet excited-state. An introduction of CMIs heavier than Mg2+ significantly improves pigments' photostabilities, however, at the expense of S1 state lifetime. Modifications of the peripheral substituents may also influence the S1 energy, and pigments’ redox potentials, which in turn influence their photostability. View Full-Text
Keywords: singlet excited state lifetime; quantum yield; pigment photostability; pigment aggregation; central metal ion; molecular symmetry singlet excited state lifetime; quantum yield; pigment photostability; pigment aggregation; central metal ion; molecular symmetry
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Karcz, D.; Boroń, B.; Matwijczuk, A.; Furso, J.; Staroń, J.; Ratuszna, A.; Fiedor, L. Lessons from Chlorophylls: Modifications of Porphyrinoids Towards Optimized Solar Energy Conversion. Molecules 2014, 19, 15938-15954.

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