NDLI: Dendritic Porphyrin–Fullerene Conjugates: Efficient Light-Harvesting and Charge-Transfer Events

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Dendritic Porphyrin–Fullerene Conjugates: Efficient Light-Harvesting and Charge-Transfer Events

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Dendritic Porphyrin–Fullerene Conjugates: Efficient Light-Harvesting and Charge-Transfer Events

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Kovacs, Christian Garcia-garibay, Miguel A. Kuzmanich, Gregory De Miguel Rojas, Gustavo Hirsch, Andreas Spänig, Fabian Guldi, Dirk M. Schlundt, Sebastian
Description	Author Affiliation: Schlundt S ( Department of Chemistry and Pharmacy and Interdisciplinary Center of Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054-Erlangen, Germany.)
Abstract	A novel dendritic $C_{60}-H_{2}P-(ZnP)_{3}$ (P=porphyrin) conjugate gives rise to the successful mimicry of the primary events in photosynthesis, that is, light harvesting, unidirectional energy transfer, charge transfer, and charge-shift reactions. Owing, however, to the flexibility of the linkers that connect the $C_{60},$ $H_{2}P,$ and ZnP units, the outcome depends strongly on the rigidity/viscosity of the environment. In an agar matrix or Triton X-100, time-resolved transient absorption spectroscopic analysis and fluorescence-lifetime measurements confirm the following sequence. Initially, light harvesting is seen by the peripheral $C_{60}-H_{2}P-$ $(ZnP)_{3}$ conjugate. Once photoexcited, a unidirectional energy transfer funnels the singlet excited-state energy to $H_{2}P$ to form $C_{60}-(H_{2}P)-(ZnP)_{3},$ which powers an intramolecular charge transfer that oxidizes the photoexcited $H_{2}P$ and reduces the adjacent $C_{60}$ species. In the correspondingly formed $(C_{60})^{.−}-(H_{2}P)^{.+}-(ZnP)_{3}$ conjugate, an intramolecular charge-shift reaction generates $(C_{60})^{.−}-H_{2}P-(ZnP)_{3}^{.+},$ in which the radical cation resides on one of the three ZnP moieties, and for which lifetimes of up to 460 ns are found. On the other hand, investigations in organic media (i.e., toluene, THF, and benzonitrile) reveal a short cut, that is, the peripheral ZnP unit reacts directly with $C_{60}$ to form $(C_{60})^{.−}-H_{2}P-(ZnP)_{3}^{.+}.$ Substantial configurational rearrangements— placing ZnP and $C_{60}$ in proximity to each other—are, however, necessary to ensure the required through space interactions (i.e., close approach). Consequently, the lifetime of $(C_{60})^{.−}-H_{2}P-(ZnP)_{3}^{.+}$ is as short as 100 ps in benzonitrile.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	45
Volume Number	15
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2009-11-16
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Dendrimers Chemistry Fullerenes Porphyrins Zinc Electron Transport Photochemistry Spectrometry, Fluorescence Stereoisomerism Structure-Activity Relationship Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S.
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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