Synthesis and fluorescence properties of side-chain carboxylated 5,9-diaminobenzo[a]phenoxazinium salts

被引：21

作者：

Frade, VHJ ^{[1
]}

Gonçalves, MST ^{[1
]}

Moura, JCVP ^{[1
]}

机构：

[1] Univ Minho, Ctr Quim, P-4710057 Braga, Portugal

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 30期

关键词：

biomarkers; benzo[a]phenoxazines; long-wavelength fluorescence probes; fluorescent dyes; cationic dyes; fluorophores;

D O I：

10.1016/j.tetlet.2005.05.105

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The efficient synthesis of a series of novel side-chain carboxylated 5,9-diaminobenzo[a]phenoxazinium salts is described. The ring system was prepared by the reaction of 5-alkylamino-2-nitrosophenol hydrochlorides with the appropriate N-alkylated-naphthylamine. Evaluation of the visible and fluorescence properties of the cationic dyes was carried out in ethanol and water at physiological pH. In both solvents they showed intense visible absorption maxima in the range 500-638 nm (ethanol) and 625-650 (water), and fluoresced strongly, with fluorescence maxima from 612 to 669 nm (ethanol) and from 654 to 685 nm (water). A wide variation in fluorescence quantum yields is observed, ranging from 0.051 to 0.50 and 0.065 to 0.32 in ethanol and water, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：4949 / 4952

页数：4

共 20 条

[1] Structural polarity and functional bile canaliculi in rat hepatocyte spheroids [J].