Tetrahydroquinoxaline based squaraines: Synthesis and photophysical properties

被引:43
作者
Chandrasekaran, Yogesh [1 ]
Dutta, Gitish K. [1 ]
Kanth, Raja Bhaskar [1 ]
Patil, Satish [1 ]
机构
[1] Indian Inst Sci, Solid State & Struct Chem Unit, Bangalore 560012, Karnataka, India
关键词
NIR dyes; Squaraines; Tetrahydroquinoxaline; Donor-acceptor-donor; Bathochromic shift; Job's plot; SINGLET OXYGEN GENERATION; SQUARYLIUM CYANINE DYES; ONE-POT SYNTHESIS; FLUORESCENT CHEMOSENSOR; PHOTOACTIVE CHEMOSENSORS; UNSYMMETRICAL SQUARAINES; PHOTODYNAMIC THERAPY; DIVALENT COPPER; ABSORBING DYES; AQUEOUS-MEDIA;
D O I
10.1016/j.dyepig.2009.04.003
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Tetrahydroquinoxaline based squaraine dyes synthesized by the condensation reaction between squaric acid and different tetrahydroquinoxaline derivatives are described. The squaraines gave a strong intense peak at 700 nm and were found to exhibit good molar extinction coefficient (>10(5) M-1 cm(-1)). Metal binding studies were carried out with different metal ions and it was found that it was selective in the case of copper metal. Using job's plot it was ascertained that the squaraines bind to the copper metal in the ratio of 2:1. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:162 / 167
页数:6
相关论文
共 66 条
[1]   Chemistry of squaraine-derived materials: Near-IR dyes, low band gap systems, and cation sensors [J].
Ajayaghosh, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (06) :449-459
[2]   Controlled self-assembly of squaraines to 1D supramolecular architectures with high molar absorptivity [J].
Ajayaghosh, Ayyappanpillai ;
Chithra, Parayalil ;
Varghese, Reji ;
Divya, Kizhumuri P. .
CHEMICAL COMMUNICATIONS, 2008, (08) :969-971
[3]   Self-assembly of tripodal squaraines: Cation-assisted expression of molecular chirality and change from spherical to helical morphology [J].
Ajayaghosh, Ayyappanpillai ;
Chithra, Parayalil ;
Varghese, Reji .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (1-2) :230-233
[4]   A squaraine-based near IR fluorescent chemosensor for calcium. [J].
Akkaya, EU ;
Turkyilmaz, S .
TETRAHEDRON LETTERS, 1997, 38 (25) :4513-4516
[5]   Selective calcium ion sensing with a bichromophoric squaraine foldamer [J].
Arunkumar, E ;
Ajayaghosh, A ;
Daub, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) :3156-3164
[6]   A comment upon the aggregation of squaraine dyes [J].
Ashwell, GJ .
JOURNAL OF MATERIALS CHEMISTRY, 1998, 8 (02) :373-376
[7]   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
[8]   A squaraine-based chemosensor for Hg2+ and Pb2+ [J].
Basheer, MC ;
Alex, S ;
Thomas, KG ;
Suresh, CH ;
Das, S .
TETRAHEDRON, 2006, 62 (04) :605-610
[9]   Near-infrared absorbing squarylium dyes [J].
Bello, KA ;
Ajayi, JO .
DYES AND PIGMENTS, 1996, 31 (02) :79-87
[10]   New π-extended water-soluble squaraines as singlet oxygen generators [J].
Beverina, L ;
Abbotto, A ;
Landenna, M ;
Cerminara, M ;
Tubino, R ;
Meinardi, F ;
Bradamante, S ;
Pagani, GA .
ORGANIC LETTERS, 2005, 7 (19) :4257-4260