1-vinylazulenes - potential host molecules in ligands for metal ion detectors

被引：18

作者：

Birzan, Liviu ^{[1
]}

Cristea, Mihaela ^{[1
]}

Draghici, Constantin C. ^{[1
]}

Tecuceanu, Victorita ^{[1
]}

Maganu, Maria ^{[1
]}

Hanganu, Anamaria ^{[1
]}

Arnold, Georgiana-Luiza ^{[2
]}

Ungureanu, Eleonora-Mihaela ^{[2
]}

Razus, Alexandru C. ^{[1
]}

机构：

[1] Roumanian Acad, Inst Organ Chem CD Nenitescu, 202B Spl Independentei, Bucharest 060023, Romania

[2] Univ Politehn Bucuresti, Fac Appl Chem & Mat Sci, 1-7 Gheorghe Polizu, Bucharest 011061, Romania

来源：

TETRAHEDRON | 2016年 / 72卷 / 18期

关键词：

Azulene; Ligands; Knoevenagel condensation; C-H activation; Bathochromic shift; Redox potentials; CONJUGATED OLIGOMERS; AZULENE DERIVATIVES; KNOEVENAGEL; POLY(4-AZULEN-1-YL-2,6-BIS(2-THIENYL)PYRIDINE); SPECTROSCOPY; CHEMISTRY; SHIFTS; STATE;

D O I：

10.1016/j.tet.2016.03.049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several vinylazulenes containing metalophilic groups were prepared as potential host molecules in ligands for metal ion detectors. The azulene-1-carbaldehyde derivatives were condensed with methylene active compounds in the presence of piperidine. The reaction is influenced by both the nature of the methylene activating groups and by the presence of the alkyl groups on the 4-,6- or 8- position of the azulene moiety. Some unusual reagents, as nitroacetate were condensed with imines activated by acetic anhydride. Several autocondensation azulenic products were evidenced in the presence of weak activated methylenes. Considerations regarding S-1 and S-2 absorption bands of the azulene compounds were revealed and correlated with frontier molecular orbitals. At the same time, the prepared ligands redox potentials were investigated by differential pulse voltammetry (DPV). (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2316 / 2326

页数：11

共 43 条

[1]

Amarandei CA, 2014, ACTA CHIM SLOV, V61, P894

[2] Stimuli-Responsive Azulene-Based Conjugated Oligomers with Polyaniline-like Properties [J].