Facile preparative redox chemistry of bis(4-dialkylaminophenyl)squaraine dyes

被引:8
作者
Griffiths, J [1 ]
Park, S [1 ]
机构
[1] Univ Leeds, Dept Colour Chem, Leeds LS2 9JT, W Yorkshire, England
关键词
squaraine dye; leuco-squaraine; redox reactions; cyclobutenone;
D O I
10.1016/S0040-4039(02)01857-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bis(4-dialkylaminophenyl)squaraine dyes are readily reduced in solution by borohydride to give alkali soluble leuco compounds, which exist in the 3-hydroxy-2,4-(4-dialkylaminophenyl)cyclobutenone tautomeric form. The leuco dyes can be oxidised rapidly back to the squaraine dye, thus providing a means of temporarily solubilising the squaraine dye in water. The leuco compounds undergo Substitution reactions typical of vinylogous carboxylic acids. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7669 / 7671
页数:3
相关论文
共 13 条
[1]   STRONG 2ND-HARMONIC GENERATION FROM CENTROSYMMETRIC DYES [J].
ASHWELL, GJ ;
JEFFERIES, G ;
HAMILTON, DG ;
LYNCH, DE ;
ROBERTS, MPS ;
BAHRA, GS ;
BROWN, CR .
NATURE, 1995, 375 (6530) :385-388
[2]   CROWN-ETHER DERIVATIVES OF SQUARAINE - NEW NEAR-INFRARED-ABSORBING, REDOX-ACTIVE FLUOROIONOPHORES FOR ALKALI-METAL RECOGNITION [J].
DAS, S ;
THOMAS, KG ;
THOMAS, KJ ;
GEORGE, MV ;
BEDJA, I ;
KAMAT, PV .
ANALYTICAL PROCEEDINGS, 1995, 32 (06) :213-215
[3]  
HAMILTON AL, 1997, Patent No. 9740104
[4]   PHOTOCHEMISTRY OF SQUARAINE DYES .1. EXCITED SINGLET, TRIPLET, AND REDOX STATES OF BIS[4-(DIMETHYLAMINO)PHENYL]SQUARAINE AND BIS[4-(DIMETHYLAMINO)-2-HYDROXYPHENYL]SQUARAINE [J].
KAMAT, PV ;
DAS, S ;
THOMAS, KG ;
GEORGE, MV .
JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (01) :195-199
[5]  
KAZMALER PM, 1988, J PHYS CHEM-US, V92, P4226
[6]  
LAW KY, 1987, J IMAGING SCI, V31, P172
[8]  
Matsuoka M., 1990, INFRARED ABSORBING D
[9]   ORGANIC SOLAR-CELLS OF HYDROXY SQUARYLIUM [J].
MERRITT, VY ;
HOVEL, HJ .
APPLIED PHYSICS LETTERS, 1976, 29 (07) :414-415
[10]  
Muthyala R., 2002, Chemistry and Applications of Leuco Dyes