Domino synthesis of protochromic "ON-OFF-ON" luminescent 2-styryl quinolines

被引：27

作者：

Cinar, Rahime ^{[1
]}

Nordmann, Jan ^{[1
]}

Dirksen, Elena ^{[1
]}

Mueller, Thomas J. J. ^{[1
]}

机构：

[1] Univ Dusseldorf, Inst Organ Chem & Makromol Chem, Lehrstuhl Organ Chem, D-40225 Dusseldorf, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 16期

关键词：

FLUORESCENT PH INDICATORS; ELECTRON-TRANSFER; NONEQUILIBRIUM SOLVATION; RANGE; COMPLEXES; SPECTRA; PROBE; MACROMOLECULES; QUINAZOLINE; BEARING;

D O I：

10.1039/c3ob27270b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The microwave-assisted coupling-isomerization reaction (MACIR) opens a straightforward domino access to 2-styryl quinolines in good to excellent yields. The push-pull character of these lumophores can be enhanced by placing a dimethyl amino group as an auxochrome in the para-position of the styryl moiety whereas anti-auxochromes are located in the 6-position of the quinoline part. The optical absorption and emission properties of the compounds were studied in solvents of different polarity and at various pH. The pronounced proto-and solvochromicity of the absorption and emission properties qualify them as luminescent pH sensors with "ON-OFF-ON" emission profiles triggered by pH variation over a broad pH range. The electronic structure of the chromophores is rationalized by DFT calculations.

引用

页码：2597 / 2604

页数：8

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