Anellated hemicyanine dyes with large symmetrical solvatochromism of absorption and fluorescence

被引:47
作者
Hübener, G [1 ]
Lambacher, A [1 ]
Fromherz, P [1 ]
机构
[1] Max Planck Inst Biochem, Dept Membrance & Neurophys, Martinsried, Germany
关键词
D O I
10.1021/jp0345809
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A novel class of amphiphilic hemicyanine dyes is described where electron-pushing aniline and electron-pulling pyridinium are joined by anellated benzene rings. Enhancing the solvent polarity, the absorption band of these ANNINE dyes is shifted to the blue and the fluorescence band is shifted to the red at an invariant 00 energy. The increasing Stokes shift spans the whole visible spectrum. The divergent symmetrical solvatochromism of the positively charged chromophores is parametrized by a monopole-dipole model using a Born-Onsager-Marcus approach. From the intramolecular charge shift that is induced by electronic excitation, the linear Stark effect that is expected when the ANNINE dyes are used as voltage-sensitive probes in a biomembrane is estimated.
引用
收藏
页码:7896 / 7902
页数:7
相关论文
共 39 条
[1]   Volumes and hydration warmth of ions [J].
Born, M .
ZEITSCHRIFT FUR PHYSIK, 1920, 1 :45-48
[2]   SOLVENT REORGANIZATION IN OPTICAL AND THERMAL ELECTRON-TRANSFER PROCESSES - SOLVATOCHROMISM AND INTRAMOLECULAR ELECTRON-TRANSFER BARRIERS IN SPHEROIDAL MOLECULES [J].
BRUNSCHWIG, BS ;
EHRENSON, S ;
SUTIN, N .
JOURNAL OF PHYSICAL CHEMISTRY, 1987, 91 (18) :4714-4723
[3]  
Bullen A, 1999, MODERN TECHNIQUES NE, P89
[4]   OPTICAL MEASUREMENT OF MEMBRANE-POTENTIAL [J].
COHEN, LB ;
SALZBERG, BM .
REVIEWS OF PHYSIOLOGY BIOCHEMISTRY AND PHARMACOLOGY, 1978, 83 :35-88
[5]   FLUORESCENCE OF AMPHIPHILIC HEMICYANINE DYES WITHOUT FREE DOUBLE-BONDS [J].
EPHARDT, H ;
FROMHERZ, P .
JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (17) :4540-4547
[6]   FLUORESCENCE AND PHOTOISOMERIZATION OF AN AMPHIPHILIC AMINOSTILBAZOLIUM DYE AS CONTROLLED BY THE SENSITIVITY OF RADIATIONLESS DEACTIVATION TO POLARITY AND VISCOSITY [J].
EPHARDT, H ;
FROMHERZ, P .
JOURNAL OF PHYSICAL CHEMISTRY, 1989, 93 (22) :7717-7725
[7]  
EPHARDT H, 1991, J PHYS CHEM-US, V95, P6729
[8]   The synthesis of 3-substituted derivatives of methylcholanthrene [J].
Fieser, LF ;
Riegel, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 :2561-2565
[9]   SPECTRA, MEMBRANE-BINDING, AND POTENTIOMETRIC RESPONSES OF NEW CHARGE SHIFT PROBES [J].
FLUHLER, E ;
BURNHAM, VG ;
LOEW, LM .
BIOCHEMISTRY, 1985, 24 (21) :5749-5755
[10]   FLUORESCENT DYES AS PROBES OF VOLTAGE TRANSIENTS IN NEURON MEMBRANES - PROGRESS REPORT [J].
FROMHERZ, P ;
DAMBACHER, KH ;
EPHARDT, H ;
LAMBACHER, A ;
MULLER, CO ;
NEIGL, R ;
SCHADEN, H ;
SCHENK, O ;
VETTER, T .
BERICHTE DER BUNSEN-GESELLSCHAFT-PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 1991, 95 (11) :1333-1345