J. Technology and Education, Vol.27, No.1, pp.27-31 (2020)
松井 栄樹*、小林 勝也、大江 真樹
福井工業高等専門学校 物質工学科 （〒916-8507 福井県鯖江市下司町）
Identification of metal complex of anthraquinone dyes having coordination site
Eiki MATSUI*, Katsuya KOBAYASHI, Masaki OE
Department of Chemistry and Biology, National Institute of Technology, Fukui College
(Geshi, Sabae, Fukui 916-8507, Japan)
(Received March 4, 2020; Accepted March 23, 2020)
The purpose of this study was to introduce a substituent having a metal coordination moiety into an anthraquinone dye and to identify the effect of the metal coordination on the quinone site using ESI-MS. 2-Amino dye 2 and 1-amino dye 4 were synthesized, and their structures were identified by APCI-MS, 1H-NMR, 13C-NMR, and DEPT45 measurements. Subsequently, ESI-MS measurement of the metal coordination of dyes 2 and 4 showed the complex formation. As a result, in the case where Zn2 +, Cu2 +, Ni2 +, and Co2 + ions were coordinated, the signals where the amino group of dye 2 was deprotonated and the metal ion was coordinated were strongly observed. On the other hand, the signals in which the metal ion and the perchlorate ion coordinated to dye 4 were strongly observed.
These differences can be attributted to the position of the metal coordination moiety. Deprotonation of the amino group and coordination at the quinone site occur which is likely to play a part in complex formation.
Keywords: anthraquinone dye, metal coordination, ESI-MS, coordination at the quinone