Premium
Synthesis of polyurethane cationomers with anil groups: intramolecular proton transfer in salicylideneanil structures
Author(s) -
Buruiana Emil C,
Olaru Mihaela,
Strat Mitache,
Strat Geta,
Simionescu Bogdan C
Publication year - 2005
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.1846
Subject(s) - aniline , intramolecular force , tautomer , polymer chemistry , polyurethane , chemistry , photochromism , molar mass , toluene , diol , photochemistry , medicinal chemistry , organic chemistry , polymer
Three new o ‐hydroxy Schiff bases, 2‐chloromethyl‐ N ‐(2‐hydroxybenzilidene)aniline, 3‐(11‐bromoundecanoyloxymethyl)‐ N ‐(2‐hydroxybenzilidene)aniline and 4‐chloromethylphenyl (carbamoyloxymethyl‐2‐hydroxybenzylidene)aniline, used as quaternization agents for a polyetherurethane precursor based on poly(tetramethylene oxide) diol of 2000 g mol −1 average molar mass (PTMO), 2,4‐toluene diisocyanate and N ‐methyldiethanolamine (1:3:2 molar ratio), have been synthesized in order to obtain polymeric films with fluorescent properties. The structure and the photochromic mechanism of the salicylideneanil units were investigated. The excited state intramolecular proton‐transfer process (ESIPT) with the cis ‐ and trans ‐keto isomers formation as intermediate compounds and the formation of a keto tautomer were evidenced by a large Stokes shifted emission (100 nm). Copyright © 2005 Society of Chemical Industry