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Synthesis of non-covalent BODIPY-metalloporphyrin dyads and triads

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Title Synthesis of non-covalent BODIPY-metalloporphyrin dyads and triads
 
Creator KHAN, TK
RAVIKANTH, M
 
Subject Boron-dipyrromethenes
Metalloporphyrins
Metal-pyridyl coordination
BODIPY-metalloporphyrin assemblies
CRYSTAL-STRUCTURE
SUPRAMOLECULAR CHEMISTRY
COORDINATION
DYES
ELECTROCHEMISTRY
SPECTROSCOPY
DERIVATIVES
PORPHYRINS
 
Description Boron-dipyrromethenes (BODIPY) containing oxypyridine substituents at 3- and 3,5-positions and metalloporphyrins (Zn(II), Ru(II)) were used to synthesize four non-covalent BODIPY-metalloporphyrin dyads and four BODIPY-metalloporphyrin triads assembled using metal pyridine 'N' interaction. The formation of BODIPY-metalloporphyrin assemblies was confirmed by 1D and 2D NMR methods and X-ray crystal structure obtained for one of the BODIPY-metalloporphyrin dyad. In H-1 NMR, the signals of oxypyridine group(s) of BODIPY unit showed significant upfield shifts supporting the coordination of oxypyridine group of BODIPY unit to metalloporphyrin unit. The NMR study also indicated that Zn(II) porphyrin forms relatively weak BODIPY-Zn(II) porphyrin conjugates, whereas Ru(II) porphyrin forms strong BODIPY-Ru(II) porphyrin conjugates. The X-ray structure solved for BODIPY-Zn(II)porphyrin dyad revealed that the Zn(II) porphyrin coordinated to the BODIPY unit obliquely and the angle between the Zn(II) porphyrin and the pyridyl ring is 70 degrees. The absorption properties of stable BODIPY-Ru(II) porphyrin conjugates showed the overlapping absorption features of both the components and the fluorescence studies indicated that the BODIPY unit emission was significantly quenched on coordination with RuTPP(CO) unit. The electrochemical studies exhibited the features of both BODIPY and metalloporphyrin units in dyads and traids. (C) 2011 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2014-10-16T06:38:39Z
2014-10-16T06:38:39Z
2012
 
Type Article
 
Identifier TETRAHEDRON, 68(3)830-840
http://dx.doi.org/10.1016/j.tet.2011.11.048
http://dspace.library.iitb.ac.in/jspui/handle/100/15454
 
Language en