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
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Creator |
KHAN, TK
RAVIKANTH, M |
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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 |
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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.
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Publisher |
PERGAMON-ELSEVIER SCIENCE LTD
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Date |
2012-06-26T08:38:40Z
2012-06-26T08:38:40Z 2011 |
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Type |
Article
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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 |
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Language |
English
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