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Synthesis and properties of hexaarylated AzaBODIPYs

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Title Synthesis and properties of hexaarylated AzaBODIPYs
 
Creator KUMAR, S
KHAN, TK
RAVIKANTH, M
 
Subject POLYARYLATED BORON-DIPYRROMETHENES
PHOTODYNAMIC THERAPY
CONJUGATED POLYMERS
CHARGE SEPARATION
BODIPY DYES
TETRAARYLAZADIPYRROMETHENES
AZADIPYRROMETHENE
PHTHALOCYANINES
PORPHYRINS
DEVICES
AzaBODIPY
Hexaarylated azaBODIPY
Electronic properties
Redox properties and C-C coupling
 
Description Sterically crowded 1,2,3,5,6,7-hexaarylated azaBODIPYs were synthesized in 25-35% yields by coupling 1,3,5,7-tetraaryl azaBODIPYs with six different aryl boronic acids under Pd(0) coupling conditions. The moderate reaction yields were attributed to steric congestion caused by two additional aryl groups introduced at the tetraaryl azaBODIPY core. The compounds were characterized by HRMS, 1D and 2D NMR spectroscopic techniques. The H-1, F-19 and B-11 NMR studies of hexaarylated azaBODIPYs showed slight upfield shifts compared to tetraaryl azaBODIPY indicating the slight alteration of electronic properties of azaBODIPY core upon introduction of two additional aryl groups on tetrararyl azaBODIPY. The absorption and fluorescence bands of hexaarylated azaBODIPYs experienced 7-10 nm hypsochromic shifts compared to tetraaryl azaBODIPY. The hexaarylated azaBODIPYs are weakly fluorescent with significant reduction in quantum yields and singlet state lifetimes compared to tetraarylated azaBODIPY. (C) 2015 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2016-01-15T05:53:32Z
2016-01-15T05:53:32Z
2015
 
Type Article
 
Identifier TETRAHEDRON, 71(40)7608-7613
0040-4020
http://dx.doi.org/10.1016/j.tet.2015.07.074
http://dspace.library.iitb.ac.in/jspui/handle/100/17864
 
Language en