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Foldamer‐Derived Preorganized Bi‐ and Tri‐zinc Porphyrin Tweezers for a Pentafluorobenzene‐bearing Pyridine Guest: The Binding Pattern Study
Author(s) -
Li Changzhi,
Zhao Xin,
Gao Xiang,
Wang Quanrui,
Li Zhanting
Publication year - 2013
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201300009
Subject(s) - chemistry , molecular tweezers , porphyrin , zinc , foldamer , pyridine , titration , tweezers , molecule , amide , crystallography , hydrogen bond , ligand (biochemistry) , proton nmr , stereochemistry , photochemistry , inorganic chemistry , medicinal chemistry , supramolecular chemistry , organic chemistry , receptor , biochemistry
By introducing two and three zinc porphyrin units to one side of hydrogen bonding‐induced aromatic amide foldamers, two new molecular tweezers 1 and 2 have been prepared. To explore new possible binding patterns, a leucine‐based pyridine ligand 3 that bears a pentafluorophenyl group has been prepared. UV‐Vis and 1 H NMR experiments reveal that 1 and 2 favorably complex one or two molecules of 3 . UV‐Vis titration experiments show that the apparent association constants of the complexes of the zinc porphyrin units of the two receptors and 3 are considerably higher than that of the complex between a simple control zinc porphyrin and 3 . In the presence of excess of 3 , the left zinc porphyrin unit of 1 and 2 can bind one more molecule of 3 , which is, however, stabilized only by the single Zn‐N coordination.