Novel semisquaraine regioisomers: isolation, divergent chemical reactivity and photophysical properties

被引:11
作者
Avirah, Rekha R. [1 ]
Jyothish, Kuthanapillil [1 ]
Suresh, Cherumuttathu H.
Suresh, Eringathodi [2 ]
Ramaiah, Danaboyina [1 ]
机构
[1] Natl Inst Interdisciplinary Sci & Technol NIIST C, Chem Sci & Technol Div, Trivandrum 695019, Kerala, India
[2] Cent Salt & Marine Chem Res Inst, Bhavnagar 364002, Gujarat, India
关键词
HALOGENATED SQUARAINE DYES; PHOTODYNAMIC THERAPY; ELECTRONIC FACTORS; CYTOTOXICITY; RECOGNITION; CHEMISTRY; DESIGN; SENSOR;
D O I
10.1039/c1cc15261k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A zwitterionic semisquaraine 1,3-regioisomer which exhibits distinct photophysical properties and chemical reactivity was isolated. Uniquely, this isomer has been identified as the reactive intermediate in the squaraine dye formation reaction rather than the neutral 1,2-isomer and opens up new avenues for the synthesis of novel dyes for optoelectronic applications.
引用
收藏
页码:12822 / 12824
页数:3
相关论文
共 38 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]  
[Anonymous], 1997, Empirical Absorption Correction Program
[3]   β-Cyclodextrin as a Photosensitizer Carrier: Effect on Photophysical Properties and Chemical Reactivity of Squaraine Dyes [J].
Arun, Kalliat T. ;
Jayaram, Dhanya T. ;
Avirah, Rekha R. ;
Ramaiah, Danaboyina .
JOURNAL OF PHYSICAL CHEMISTRY B, 2011, 115 (21) :7122-7128
[4]   Near-infrared fluorescent probes: Synthesis and spectroscopic investigations of a few amphiphilic squaraine dyes [J].
Arun, KT ;
Ramaiah, D .
JOURNAL OF PHYSICAL CHEMISTRY A, 2005, 109 (25) :5571-5578
[5]   Dual-mode semisquaraine-based sensor for selective detection of Hg2+ in a micellar medium [J].
Avirah, Rekha R. ;
Jyothish, Kuthanapillil ;
Ramaiah, Danaboyina .
ORGANIC LETTERS, 2007, 9 (01) :121-124
[6]   Assessment of water-soluble π-extended squaraines as one- and two-photon singlet oxygen photosensitizers:: Design, synthesis, and characterization [J].
Beverina, Luca ;
Crippa, Maurizio ;
Landenna, Mirko ;
Ruffo, Riccardo ;
Salice, Patrizio ;
Silvestri, Fabio ;
Versari, Silvia ;
Villa, Alessandro ;
Ciaffoni, Luca ;
Collini, Elisabetta ;
Ferrante, Camilla ;
Bradamante, Silvia ;
Mari, Claudio M. ;
Bozio, Renato ;
Pagani, Giorgio A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (06) :1894-1902
[7]   Squaraine Compounds: Tailored Design and Synthesis towards a Variety of Material Science Applications [J].
Beverina, Luca ;
Salice, Patrizio .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (07) :1207-1225
[8]   AN MNDO AND CNDO/S(S + DES CI) STUDY ON THE STRUCTURAL AND ELECTRONIC-PROPERTIES OF A MODEL SQUARAINE DYE AND RELATED CYANINE [J].
BIGELOW, RW ;
FREUND, HJ .
CHEMICAL PHYSICS, 1986, 107 (2-3) :159-174
[9]   A novel blue dye for near-IR 'dye-sensitised' solar cell applications [J].
Burke, Anthony ;
Schmidt-Mende, Lukas ;
Ito, Seigo ;
Gratzel, Michael .
CHEMICAL COMMUNICATIONS, 2007, (03) :234-236
[10]   MOLECULAR FIRST HYPERPOLARIZABILITIES OF A NEW CLASS OF ASYMMETRIC SQUARAINE DYES [J].
CHEN, CT ;
MARDER, SR ;
CHENG, LT .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) :259-260