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Synthesis of novel phenylazomethine derivatives as a multi‐dentate ligand for advanced metal‐organic hybride nano‐materials
Author(s) -
Yamamoto Kimihisa
Publication year - 2003
Publication title -
macromolecular symposia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.257
H-Index - 76
eISSN - 1521-3900
pISSN - 1022-1360
DOI - 10.1002/masy.200390156
Subject(s) - trimer , aniline , imine , chemistry , molecule , ligand (biochemistry) , substituent , tin , polymer chemistry , stereochemistry , organic chemistry , dimer , biochemistry , receptor , catalysis
Oligophenylazomethines (OPAs) and the aniline‐capped OPAs were synthesized via dehydration of 4‐aminobenzophenone in the presence of TiCl 4 as a Lewis acid. TiCl 4 acts as an excellent dehydration agent for formation of the C=N bond. OPAs have some isomers, which are based on the E/Z conformation of the azomethine moieties. Novel cyclic molecules, the cyclic phenylazomethine trimer (CPA 3 ‐ab) derivatives, were synthesized via the dehydration of the 4‐aminobenzophenone. The yields of the macrocycles were enhanced to over 90% by induction of the bulky α‐substituent to the substrate. The highly preferential formation of novel aabb‐type phenylazo‐methine macrocycles was also achieved. The resulting CPA 6 ‐aabb has unique structure based on the E/Z conformation of the azomethine bonds, the extremely regular molecular‐packing state. The novel dendritic phenylazomethines(DPAs), were synthesized by the convergent method. The DPAs have a high solubility unlike the conventional linear polyphenylazomethines. The tin chloride complexed to the imine groups of DPAs in a stepwise fashion. The complexation occurs in the order of 1st, 2nd, 3rd, and 4th layers of DPA G4.