TY - JOUR
T1 - Molecular Association of Water-Soluble Calixarenes with Several Stilbene Dyes and Its Application to the Facile Determination of Cationic Surfactant Concentrations
AU - Nishida, Masashi
AU - Ishii, Daido
AU - Yoshida, Isao
AU - Shinkai, Seiji
N1 - Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.
PY - 1997/9
Y1 - 1997/9
N2 - The molecular association of water-soluble p-sulfonatocalix[n]arenes (1n; n = 4, 6, and 8) with several stilbene dyes (D) has been studied by spectrophotometric and 1HNMR methods. It was found that 1n reacts in 1: 1 stoichiometry with, D such as 4-[(4-dimethylamino)styryl]-1-methylpyridinium (St-4Me), 2-[(4-dimethylamino)styryl]-1-methylpyridinium (St-2Me) and 2-[(4-dimethylamino)styryl]-1-ethylpyridinium (St-2Et) iodides to form their complexes (1nD). The apparent association constants for 18-complexes are larger by about ten times than those of 14- and 16-complexes. Examinations of the CPK molecular models and the spectrophotometric studies suggested that 14 complexes D mainly with its 1-methyl- or 1-ethylpyridinium group, whereas 16 complexes D either with its pyridinium ring or with its protonated dimethylamino group in a similar probability, and in 18-complexes the molecule is wholly incorporated into the cavity of 18. The absorbance of D, which was decreased by association with 1n, was regenerated by the addition of other colorless cationic surfactants (A) such as cetylethyldimethylammonium ion. Studies on the substitution reaction of 1nD with A indicated that a 1 : 1 complex (1nA) is formed by releasing a free dye molecule (D). This was applied to a convenient determination of the cationic surfactant concentration in water.
AB - The molecular association of water-soluble p-sulfonatocalix[n]arenes (1n; n = 4, 6, and 8) with several stilbene dyes (D) has been studied by spectrophotometric and 1HNMR methods. It was found that 1n reacts in 1: 1 stoichiometry with, D such as 4-[(4-dimethylamino)styryl]-1-methylpyridinium (St-4Me), 2-[(4-dimethylamino)styryl]-1-methylpyridinium (St-2Me) and 2-[(4-dimethylamino)styryl]-1-ethylpyridinium (St-2Et) iodides to form their complexes (1nD). The apparent association constants for 18-complexes are larger by about ten times than those of 14- and 16-complexes. Examinations of the CPK molecular models and the spectrophotometric studies suggested that 14 complexes D mainly with its 1-methyl- or 1-ethylpyridinium group, whereas 16 complexes D either with its pyridinium ring or with its protonated dimethylamino group in a similar probability, and in 18-complexes the molecule is wholly incorporated into the cavity of 18. The absorbance of D, which was decreased by association with 1n, was regenerated by the addition of other colorless cationic surfactants (A) such as cetylethyldimethylammonium ion. Studies on the substitution reaction of 1nD with A indicated that a 1 : 1 complex (1nA) is formed by releasing a free dye molecule (D). This was applied to a convenient determination of the cationic surfactant concentration in water.
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U2 - 10.1246/bcsj.70.2131
DO - 10.1246/bcsj.70.2131
M3 - Article
AN - SCOPUS:0000294217
VL - 70
SP - 2131
EP - 2140
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
SN - 0009-2673
IS - 9
ER -