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Synthesis and properties of triazole bridged BODIPY-conjugates

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Title Synthesis and properties of triazole bridged BODIPY-conjugates
 
Creator GANAPATHI, E
MADHU, S
RAVIKANTH, M
 
Subject BODIPY
Chromophores
Click chemistry
BF2-smaragdyrin
Energy transfer
BORON DIPYRROMETHENE DYES
ENERGY-TRANSFER
SPECTROSCOPIC PROPERTIES
FUNCTIONALIZED BORON
SPECTRAL PROPERTIES
FLUORESCENT SENSOR
BUILDING-BLOCKS
LIVING CELLS
DERIVATIVES
CHEMISTRY
 
Description A series of triazole bridged BODIPY-conjugates were synthesized under click reaction conditions. The 3-azido BODIPY was generated in situ by treating 3-bromo BODIPY with NaN3 in CH3CN at room temperature for 60 min and reacted with appropriate ethynyl containing chromophore/redox active unit, such as ferrocene, BODIPY, Zn(II) porphyrin, 21,23-dithiaporphyrin, BF2-smaragdyrin in the presence of CuI/DIPEA in THF/CH3CN solvent. The conjugates were purified by column chromatography and obtained pure compounds in 45-50% yields. The conjugates were characterized by HR-MS, 1D, 2D, F-19 and B-11 NMR and X-ray crystallography for BODIPY-ferrocene conjugate. Absorption and electrochemical studies showed features of both the moieties present in the conjugates and also support interaction between the two moieties in the conjugates. The fluorescence studies supported an efficient energy transfer from BODIPY unit to BF2-smaragdyrin unit in BODIPY BF2-smaragdyrin conjugate but the energy transfer was not efficient in BODIPY-Zn(II) porphyrin and BODIPY-21,23-dithiaporphyrin conjugates. (C) 2013 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2014-12-29T05:18:26Z
2014-12-29T05:18:26Z
2014
 
Type Article
 
Identifier TETRAHEDRON, 70(3)664-671
0040-4020
http://dx.doi.org/10.1016/j.tet.2013.11.091
http://dspace.library.iitb.ac.in/jspui/handle/100/17174
 
Language English