1,1-dicyano-2-[6-(dimethylamino)naphthalen-2-yl]propene (DDNP): A solvent polarity and viscosity sensitive fluorophore for fluorescence microscopy

被引：92

作者：

Jacobson, A

Petric, A

Hogenkamp, D

Sinur, A

Barrio, JR

机构：

[1] UNIV CALIF LOS ANGELES,SCH MED,DEPT MOLEC & MED PHARMACOL,LOS ANGELES,CA 90095

[2] UNIV CALIF LOS ANGELES,SCH MED,LAB STRUCT BIOL & MOL MED,LOS ANGELES,CA 90095

[3] UNIV LJUBLJANA,FAC CHEM & CHEM TECHNOL,LJUBLJANA 6100,SLOVENIA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1996年 / 118卷 / 24期

关键词：

fluorescence; environmental sensitivity; conformers;

D O I：

10.1021/ja9543356

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

1,1-Dicyano-2-[6-(dimethylamino)naphthalen-2=yl]propene (II, DDNP) has been synthesized as a fluorescent dye whose intramolecular rotational relaxation is solvent polarity and viscosity dependent. Its fluorescence emission (lambda max: 470-610 nm in hydrophobic and viscous environments) is in a very favorable region for its use with visible fluorescence microscopy, without interference from cell or tissue autofluorescence. Its fluorescence emission quantum yield in an aqueous environment is very low, allowing for facile differentiation between lipid or protein bound state and aqueous media. II crystallizes into two solid isoforms containing one (red crystals) and two conformers (yellow crystals), exhibiting differing spectral properties. X-ray crystal structures reveal a planar arrangement between dimethylamino and naphthalenyl moieties, with out-of-plane arrangements between the malononitrile and naphthalene ring found in each of the three conformers.

引用

页码：5572 / 5579

页数：8

共 42 条

[1]

ARSENIJEVIC L, 1988, ORG SYNTH, V6, P34

[2] SOME REMARKS ON THE INTERPRETATION OF THE SPECTRAL PROPERTIES OF PRODAN [J].