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Preparation of a Highly Alkyl‐substituted Bis(8‐hydroxyquinoline) Derivative and Its Use for the Self‐Assembly of a Lipophilic Helicate with an Internal Binding Site for Cationic Guests
Author(s) -
Albrecht Markus,
Blau Oliver,
Zauner Jeanette
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(199911)1999:11<3165::aid-ejoc3165>3.0.co;2-q
Subject(s) - chemistry , cationic polymerization , 8 hydroxyquinoline , bromide , alkyl , derivative (finance) , halogenation , solubility , ethylene , combinatorial chemistry , medicinal chemistry , benzyl bromide , self assembly , polymer chemistry , organic chemistry , catalysis , financial economics , economics
The tetra‐decyl‐substituted ethylene‐linked bis(8‐hydroxyquinoline) derivative 9‐H 2 is synthesized in an eight step procedure starting from 3‐ n ‐decyl‐8‐methoxyquinoline ( 1 ). NBS‐bromination followed by a Suzuki‐reaction enables the introduction of a decyl chain in the 5‐position. In the key step of the sequence a mild (Ph 3 P) 2 NiBr 2 ‐catalyzed homo‐coupling reaction of the benzyl bromide 7 is performed. In the presence of cationic templates (M + = Na + , K + , NH 4 + ) compound 9‐H 2 reacts with gallium(III) ions to form dinuclear complexes [M⊂{( 9 ) 3 Ga 2 }]Cl in template‐directed self‐assembly processes. For the first time helicate‐type cryptates are obtained which show good solubility in apolar solvents.