Synthesis of crownophanes possessing bipyridine moieties:: bipyridinocrownophanes exhibiting perfect extractability toward Ag+ ion

被引：8

作者：

Inokuma, Seiichi ^{[1
]}

Kuramami, Masahiro ^{[1
]}

Otsuki, Shinji ^{[1
]}

Shirakawa, Tetsuyuki ^{[1
]}

Kondo, Shi-ichi ^{[1
]}

Nakamura, Yosuke ^{[1
]}

Nishimura, Jun ^{[1
]}

机构：

[1] Gunma Univ, Dept Nanomat Syst, Grad Sch Engn, Kiryu, Gumma 3768515, Japan

来源：

TETRAHEDRON | 2006年 / 62卷 / 42期

关键词：

crown compound; cyclophane; extraction; Ag+-selective ionophore; 2+2] photocycloaddition;

D O I：

10.1016/j.tet.2006.08.005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel crownophanes with two bipyridine moieties (bipyridinocrownophanes la and 1b) were conveniently prepared by means of intramolecular [2+2] photocycloaddition of vinylbipyridine derivatives. In the liquid-liquid extraction of heavy metal cations, la and 1b exhibited perfect selectivity toward Ag+ with high efficiency. It was found that the ethereal oxygen atoms and the four nitrogen atoms in 1a and 1b acted as ligating sites, according to the high extractability and complexing stability constant for Ag+ compared to those of the corresponding pyridinocrownophanes 4a and 4b. H-1 NMR and ESI-MS analyses suggested that the crownophanes formed a 1:1 complexes with the Ag+ ion. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：10005 / 10010

页数：6

共 3 条

[1] Synthesis of crownophane possessing pyridine moieties on the aromatic nuclei (pyridine-lariat crownophane):: A crownophane exhibiting perfect selectivity toward Ag+
Inokuma, S
Kimura, K
Funaki, T
Nishimura, J
HETEROCYCLES, 2001, 55 (03) : 447 - 451
[2] TRIDENTATE PYRIDINE PODAND IONOPHORES EXHIBITING PERFECT AG+ ION SELECTIVITY
TSUKUBE, H
UENISHI, J
KOJIMA, N
YONEMITSU, O
TETRAHEDRON LETTERS, 1995, 36 (13) : 2257 - 2260
[3] Benzimidazole Conjugate of 1,1′-Thiobis(2-naphthol) as Switch-On Fluorescence Receptor for Ag+ and the Complex as Secondary Recognition Ensemble toward Cys, Asp, and Glu in Aqueous Methanolic Solution: Synthesis, Characterization, Ion and Amino Acid Recognition, Computational Studies, and Microscopy Features
Dessingou, Jayaraman
Mitra, Atanu
Tabbasum, Khatija
Baghel, Garima Singh
Rao, Chebrolu P.
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01): : 371 - 378

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