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[3.3]‐ and [4.4](2,7)Pyrenophanes as Excimer Models: Synthesis, Molecular Structure, and Spectroscopic Properties
Author(s) -
Staab Heinz A.,
Riegler Norbert,
Diederich François,
Krieger Claus,
Schweitzer Dieter
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.19841170119
Subject(s) - chemistry , excimer , dehydrogenation , planarity testing , pyrene , benzoxazole , fluorescence , pyrolysis , photochemistry , stereochemistry , crystallography , organic chemistry , physics , quantum mechanics , catalysis
Abstract As excimer models the [3.3]‐ and [4.4]pyrenophanes 1 and 2 were synthesized. As the key precursor for the synthesis of 1 the octahydro‐dithia[4.4]pyrenophane 9 was obtained by cyclisation of 4 and 8 , the syntheses of which are described. Disulfone 10 , derived from 9 , on vapour‐phase pyrolysis yielded 11 which by dehydrogenation was converted into 1 . In an analogous route 2 was obtained via 16, 17 , and 18 starting from 4 and 15 (prepared in the reaction sequence 12 → 13 → 14 → 15 ). – The molecular structures of 1 and 2 , determined by X‐ray structure analyses, are discussed with regard to transanular distances and deviations from planarity of the pyrene units. – Absorption spectra of 1 and 2 are discussed with reference to transanular interactions. The fluorescence emissions of 1 and 2 are found to be ‘excimer‐like’. Results obtained by ODMR measurements of 1 are reported.