Das Sammeln von Licht und die Energieübertragung in neuen konvergent aufgebauten Dendrimeren

Light harvesting and energy transfer have received considerable attention in the literature because of their important role in natural photosynthesis. These processes involve the use of a light-absorbing antenna (donor) moiety that is capable of transferring the absorbed energy to a nearby secondary energy acceptor species. The energy-transfer process is influenced by the spatial relationship of the donor and acceptor chromophores, and recently researchers have sought to mimic the efficient arrangements found in nature. These include chromophore-functionalized polymers, [1] dendrimers, [2] supported Langmuir ± Blodgett films, [3] thin films, [4] and microspheres. [5] Here, we report the use of self-assembled monolayers (SAMs) to align the donor and acceptor chromophores and facilitate intermolecular energy transfer. Intermolecular interactions between adjacent adsorbates have previously been applied to improve the chemical stability of monolayers [6] and to facilitate surface-directed polymerization [7] or surface-confined photodimerization. [8] We extend the exploration of these interactions to include long-range photo-induced Förster energy transfer [9] between donor and acceptor chromophores on SAMs. This process involves a through-space dipole ± dipole interaction that does not occur by ªhoppingº through bonds. Energy transfer can thus be facilitated by assembly of donor and acceptor chromophores as mixed monolayers.We have recently reported efficient light harvesting by chromophore-labeled dendrimers in which light is funneled through space by Förster energy transfer from multiple coumarin-2 (1) donor dyes at the dendrimer periphery to a single coumarin-343 (2) acceptor chromophore. [10] These dyes were also chosen for our chromophore-labeled monolayers 2.

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Surface-Confined Light Harvesting, Energy Transfer, and Amplification of Fluorescence Emission in Chromophore-Labeled Self-Assembled Monolayers

Chrisstoffels

Adronov

Fréchet

2000

Angewandte Chemie

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The First Dendrimer‐Based Enantioselective Fluorescent Sensor for the Recognition of Chiral Amino Alcohols

Pugh

2000

Angewandte Chemie

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The development of fluorescence-based molecular sensors has received broad attention in research in recent years. [1±3] The use of fluorescence spectroscopic methods for molecular recognition has many advantages: fluorescence provides many more signaling modes for substrate detection, such as quenching, fluorescence enhancement, excimers, exciplexes, and lifetimes, than electronic absorption. The high sensitivity of fluorescence techniques requires the use of only very small amounts of sensor molecules. Fluorescence spectrometers are also of low cost and widely available. Fluorescence sensors can be further applied to continuous monitoring and remote sensing by using optical fibers. A large number of fluorescent sensors have been designed for applications in the detection of metal ions, phosphates, and neutral molecules. [1±3] Recently, a fluorescent sensor has also been used in the combinatorial search for catalysts. [4a] If such fluorescent sensors could be made enantioselective, they would allow a rapid analysis of the enantiomeric composition of thousands of chiral molecules generated by the combinatorial synthesis. This process would greatly facilitate the combinatorial discovery of asymmetric catalysts or reagents since the current chromatographic analysis of enantiomers is inherently a slow process. An enzyme-catalyzed release of fluorophores has been used in the search for catalytic antibodies for the enantioselective hydrolysis of acetates. [4b] Chiral discrimination by luminescence has also been studied in the past two decades. [5±9] These studies involve a variety of luminescent materials including inorganic complexes, [5] organic molecules, [6±8] and enzymes. [9] Enantioselective responses have been observed when chiral luminophores are treated with chiral quenchers or enhancers. The relationship between the fluorescence properties of the sensors and the enantiomeric purity of the substrates have been established in a few cases. [5b, 6g, 7, 9b] Recently, we carried out a program to incorporate chiral dendrimers [10] into enantioselective fluorescent sensors as a real-time technique to quantitatively or semi-quantitatively determine the enantiomeric composition of chiral molecules. Properly designed dendritic materials have been found to show efficient migration of energy from the dendrons or periphery groups to the more conjugated units or core, which has led to greatly enhanced fluorescence intensity. [11±17] The strong fluorescence signals of such dendrimers should be very useful in the development of fluorescent sensors. Based on the structure of chiral 1,1'-bi-2-naphthol ((S)-1) [18] and the den- [6] For other representative metal-free asymmetric catalysts that do not employ peptides, see: a) Y.

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First Generation Light-Harvesting Dendrimers with a [Ru(bpy)3]2+ Core and Aryl Ether Ligands Functionalized with Coumarin 450

2000

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Das Sammeln von Licht und die Energieübertragung in neuen konvergent aufgebauten Dendrimeren

Cited by 48 publications

References 31 publications

Surface-Confined Light Harvesting, Energy Transfer, and Amplification of Fluorescence Emission in Chromophore-Labeled Self-Assembled Monolayers

Surface-Confined Light Harvesting, Energy Transfer, and Amplification of Fluorescence Emission in Chromophore-Labeled Self-Assembled Monolayers

The First Dendrimer‐Based Enantioselective Fluorescent Sensor for the Recognition of Chiral Amino Alcohols

First Generation Light-Harvesting Dendrimers with a [Ru(bpy)3]2+ Core and Aryl Ether Ligands Functionalized with Coumarin 450

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