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1,8‐Dipyrenylnaphthalenes: Syntheses, Molecular Structure, and Spectroscopic Properties
Author(s) -
Wahl Peter,
Krieger Claus,
Schweitzer Dieter,
Staab H. A.
Publication year - 1984
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19841170120
Subject(s) - chemistry , pyrene , excimer , isomerization , fluorescence , stereochemistry , molecule , crystallography , organic chemistry , optics , physics , catalysis
Abstract Syntheses of the 1,8‐dipyrenylnaphthalenes 1 – 3 are reported. The stereoisomers 1 and 2 were separated; their structural assignment is based on 1 H 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.