Synthesis of Water-Soluble Cyclophane Hexamers Having a Triphenylene Core and Their Enhanced Guest-Binding Behavior.
A key compound, a precursor of water-soluble cyclophane hexamer, was prepared via Williamson ether synthesis of tetraaza[6.1.6.1]paracyclophane derivatives bearing a bromoacetamide moiety with triphenylene-2,3,6,7,10,11-hexaol as a core. A cationic cyclophane hexamer (1) was obtained by removing the protecting groups from the precursor. Fluorescence titration experiments proved that cationic cyclophane hexamer 1 showed macrocyclic multivalency effects; i.e., 1:1 host/guest binding constants (K) of 1 with anionic guests, 6-anilinonaphthalene-2-sulfonate and 6-p-toluidinonaphthalene-2-sulfonate, were increased about 63- and 62-fold, respectively, relative to those of monomeric cyclophane. Similarly, anionic cyclophane hexamer 2, which was easily prepared from 1, showed macrocyclic multivalency effects in K values with cationic guests such as hydrochlorides of doxorubicin and daunorubicin as an anticancer drug.
Department of Chemistry, Faculty of Science, Fukuoka University , 8-19-1 Nanakuma, Fukuoka 814-0180, Japan.
Osamu
O
Hayashida
Department of Chemistry, Faculty of Science, Fukuoka University , 8-19-1 Nanakuma, Fukuoka 814-0180, Japan.
Toshikazu
T
Matsuo
Department of Chemistry, Faculty of Science, Fukuoka University , 8-19-1 Nanakuma, Fukuoka 814-0180, Japan.
Kazuhiro
K
Nakamura
Department of Chemistry, Faculty of Science, Fukuoka University , 8-19-1 Nanakuma, Fukuoka 814-0180, Japan.
Shuhei
S
Kusano