Microwave-Assisted Synthesis of Near-Infrared Fluorescent Indole-Based Squaraines

被引:65
作者
Barbero, Nadia [1 ,2 ]
Magistris, Claudio [1 ,2 ]
Park, Jinhyung [1 ,2 ]
Saccone, Davide [1 ,2 ]
Quagliotto, Pierluigi [1 ,2 ]
Buscaino, Roberto [1 ,2 ]
Medana, Claudio [3 ]
Barolo, Claudia [1 ,2 ]
Viscardi, Guido [1 ,2 ]
机构
[1] Univ Turin, Dept Chem, I-10125 Turin, Italy
[2] Univ Turin, NIS Interdept Ctr, I-10125 Turin, Italy
[3] Univ Turin, Dipartimento Biotecnol Mol & Sci Salute, I-10125 Turin, Italy
关键词
SENSITIZED SOLAR-CELLS; QUATERNARY AMMONIUM-SALTS; ORGANIC-SYNTHESIS; CYANINE DYES; NANOCRYSTALLINE TIO2; PHOTOSENSITIZERS; ABSORPTION; DESIGN; OVENS; ALKYL;
D O I
10.1021/acs.orglett.5b01453
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A microwave-assisted method for the preparation of a wide color range of 2,3,3-trimethylindolenine-based squaraines and their intermediates is described. This practical approach allows the rapid preparation of both symmetrical and nonsymmetrical Squaraine dyes, reducing reaction time from days to minutes with more than 2-fold improvement in product yields when compared to,conventional methods.
引用
收藏
页码:3306 / 3309
页数:4
相关论文
共 45 条
[1]   Squaraine dyes in PDT: from basic design to in vivo demonstration [J].
Avirah, Rekha R. ;
Jayaram, Dhanya T. ;
Adarsh, Nagappanpillai ;
Ramaiah, Danaboyina .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (05) :911-920
[2]   The different kinetic behavior of two potential photosensitizers for PDT [J].
Barbero, Nadia ;
Visentin, Sonja ;
Viscardi, Guido .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2015, 299 :38-43
[3]   Twists and Turns Around a Square: The Many Faces of Squaraine Chemistry [J].
Beverina, Luca ;
Sassi, Mauro .
SYNLETT, 2014, 25 (04) :477-490
[4]   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
[5]   Microwave-assisted synthesis of near-infrared fluorescent sphingosine derivatives [J].
Bhushan, Kumar R. ;
Liu, Fangbing ;
Misra, Preeti ;
Frangioni, John V. .
CHEMICAL COMMUNICATIONS, 2008, (37) :4419-4421
[6]   Theoretical and experimental determination of the absorption and emission spectra of a prototypical indolenine-based squaraine dye [J].
Borrelli, Raffaele ;
Ellena, Silvano ;
Barolo, Claudia .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2014, 16 (06) :2390-2398
[7]   Squaraine-Arylamine Sensitizers for Highly Efficient p-Type Dye-Sensitized Solar Cells [J].
Chang, Chia-Hao ;
Chen, Yung-Chung ;
Hsu, Chih-Yu ;
Chou, Hsien-Hsin ;
Lin, Jiann T. .
ORGANIC LETTERS, 2012, 14 (18) :4726-4729
[8]   Parameters Affecting the Microwave-Specific Acceleration of a Chemical Reaction [J].
Chen, Po-Kai ;
Rosana, Michael R. ;
Dudley, Gregory B. ;
Stiegman, A. E. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16) :7425-7436
[9]   One-Pot-One-Step, Microwave-Assisted Fischer Indole Synthesis [J].
Creencia, Evelyn Cuevas ;
Tsukamoto, Masayuki ;
Horaguchi, Takaaki .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (05) :1095-1102
[10]   Enhancing the efficiency of a dye sensitized solar cell due to the energy transfer between CdSe quantum dots and a designed squaraine dye [J].
Etgar, Lioz ;
Park, Jinhyung ;
Barolo, Claudia ;
Lesnyak, Vladimir ;
Panda, Subhendu K. ;
Quagliotto, Pierluigi ;
Hickey, Stephen G. ;
Nazeeruddin, Md K. ;
Eychmueller, Alexander ;
Viscardi, Guido ;
Graetzel, Michael .
RSC ADVANCES, 2012, 2 (07) :2748-2752