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1,8‐dipyrenylnaphthalenes: syntheses, molecular structure, and spectroscopic properties

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Wahl,  Peter
Max Planck Institute for Medical Research, Max Planck Society;

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Krieger,  Claus
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Schweitzer,  Dieter
Department of Molecular Physics, Max Planck Institute for Medical Research, Max Planck Society;

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Staab,  Heinz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Wahl, P., Krieger, C., Schweitzer, D., & Staab, H. A. (1984). 1,8‐dipyrenylnaphthalenes: syntheses, molecular structure, and spectroscopic properties. Chemische Berichte, 117(1), 260-276. doi:10.1002/cber.19841170120.


Cite as: https://hdl.handle.net/21.11116/0000-0005-AEC9-5
Abstract
Syntheses of the 1,8‐dipyrenylnaphthalenes 1 – 3 are reported. The stereoisomers 1 and 2 were separated; their structural assignment is based on 1H NMR, on the optical activity of 2, and on X‐ray structure analyses of 1 and 2. Kinetic parameters for the isomerisation 2 ⇌ 1 were determined by optical rotation measurements. – Emission spectra of 1 – 3 are discussed in comparison to monopyrenyl compounds 4 and 8. For 1 and 3 typical ‘excimer‐like’ fluorescence is observed. The difference between 1 and 2 clearly demonstrates the dependence of excimer interactions between the pyrene units on the mutual orientation of the π‐systems involved. – On the basis of X‐ray analyses the molecular structures of 1 – 3 are discussed with emphasis on π…π‐interactions between the pyrene units.