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Bis(pyrrolo)tetrathiafulvalene – An Efficient π‐Donor in Supramolecular Chemistry
Author(s) -
Lau Jesper,
Brøndsted Nielsen Mogens,
Thorup Niels,
Cava Michael P.,
Becher Jan
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199912)1999:12<3335::aid-ejoc3335>3.0.co;2-i
Subject(s) - tetrathiafulvalene , chemistry , supramolecular chemistry , hydroquinone , catenane , acceptor , electron donor , photochemistry , electron acceptor , stereochemistry , crystallography , combinatorial chemistry , organic chemistry , molecule , crystal structure , catalysis , physics , condensed matter physics
The synthesis of three novel macrocycles 3–5 based on the two electron donors bis(2,5‐dimethylpyrrolo)[3,4‐ d ]tetrathiafulvalene ( 1 ) and 1,4‐hydroquinone is presented. Their abilities to include the electron acceptor paraquat ( 6 ) have been investigated by UV/Vis and 1 H NMR spectroscopy and an X‐ray crystallographic analysis. Also, the complex formation between the cyclic acceptor cyclobis(paraquat‐ p ‐phenylene) ( 7 ) and different tetrathiafulvalene derivatives has been studied. A strong association between 1 and 7 facilitates the self‐assembly of catenanes from the macrocycles 3–5 . However, the preferred position of the cyclic acceptor 7 in the catenanes around either the pyrrolo‐annelated TTF or around the hydroquinone donor relies on a fine balance between all the individual noncovalent forces acting in cooperation.