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Synthesis of covalently linked boron-dipyrromethene-chromophore conjugates using 3-bromo boron-dipyrromethene as a key precursor

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Title Synthesis of covalently linked boron-dipyrromethene-chromophore conjugates using 3-bromo boron-dipyrromethene as a key precursor
 
Creator KHAN, TK
RAVIKANTH, M
 
Subject ENERGY-TRANSFER
BUILDING-BLOCKS
BODIPY DYES
ELECTROGENERATED CHEMILUMINESCENCE
STRUCTURAL CONTROL
COUPLING REACTIONS
APPENDED SYSTEMS
BORADIAZAINDACENE
PORPHYRIN
ELECTROCHEMISTRY
Boron-dipyrromethene
Chromophores
Anthracene
Porphyrin
Sapphyrin
Energy transfer
 
Description 3-Bromo boron dipyrromethene (3-bromo BODIPY) has been used as key synthon to prepare one ethynyl bridged and six ethynylphenyl bridged BODIPY-chromophore conjugates using mild Pd(0) coupling conditions. The chromophores possessing very distinct features, such as anthracene, BODIPY, terpyridine, porphyrin. Zn(II)porphyrin, 21,23-dithiaporphyrin and thiasapphyrin were connected at 3-position of boronboron-dipyrromethene dye by coupling of 3-bromo BODIPY with ethynyl or ethynylphenyl chromophore in toluene/triethylamine in the presence of catalytic amount of AsPh(3)/Pd(2)(dba)(3) at 40 degrees C followed by column chromatographic purification. The spectral studies indicated that the interaction is stronger in ethynyl bridged BODIPY-chromophore conjugate compared to ethynylphenyl bridged BODIPY-chromophore conjugates. The steady-state fluorescence indicated that in ethynyl bridged BODIPY-anthracene conjugate, the BODIPY unit act as energy acceptor and showed a possibility of energy transfer from donor anthracene unit to acceptor BODIPY unit on selective excitation of anthracene unit. However, in ethynylphenyl bridged BODIPY-porphyrin conjugates, the BODIPY unit act as energy donor and exhibited a possibility of singlet-singlet energy transfer from BODIPY unit to porphyrin unit. (C) 2011 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2012-06-26T08:38:40Z
2012-06-26T08:38:40Z
2011
 
Type Article
 
Identifier TETRAHEDRON,67(32)5816-5824
0040-4020
http://dx.doi.org/10.1016/j.tet.2011.05.089
http://dspace.library.iitb.ac.in/jspui/handle/100/14202
 
Language English