Synthesis and complexation properties of new azophenol type and phenol blue type chromogenic acyclic crown ethers

Abstract

Two types of new chromogenic acyclic crown ethers were synthesized from the diphenols 1a and 1b in alkaline solutions. One is azophenol compounds 2a and 2b. They were produced by reacting 1a and 1b with p- nitro-benzenediazonium fluoroborate separately. The other one is phenol blue type compounds 3a and 3b. They were obtained from the oxidative condensation of 1a and 1b with N, N-dimethyl-p- phenylenediamine promoted by K~3[Fe(CN)~6]. Their properties of complexation with alkali and alkaline earth metal ions have been investigated by means of UV-visible spectrometry. It was observed that 2a has apparently selective coloration properties with LiClO~4 and Ca(ClO~4)~2 but 2b was selectively colored with LiClO~4, NaClO~4 and Ca(ClO~4)~2 in THF-H~2O (95:5, v/v). 3a and 3b exhibited some degrees of coloration with Li^+, Na^+ and several alkaline metal ions, especially with Ca^2^+, Sr^2^+ and Ba^2^+ in CH~3CN. These results show that the complexation properties of 2a and 2b are similar to 2'a and 2'b, and 3a and 3b similar to 3'b.

Key words: CROWN ETHER, ULTRAVIOLET SPECTROPHOTOMETRY

CLC Number:

O621

Cite this article

HUANG SHU;MENG JIE;TIAN BAOZHI. Synthesis and complexation properties of new azophenol type and phenol blue type chromogenic acyclic crown ethers[J]. Chin. J. Org. Chem., 1996, 16(4): 328-334.

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