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Synthesis of Covalently Linked Unsymmetrical Porphyrin Pentads Containing Three Different Porphyrin Subunits

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Title Synthesis of Covalently Linked Unsymmetrical Porphyrin Pentads Containing Three Different Porphyrin Subunits
 
Creator RAI, S
RAVIKANTH, M
 
Subject light-harvesting arrays
excited-state photodynamics
corrole dyads
electronic communication
building-blocks
multiporphyrin arrays
crystal-structure
thiophene diols
rational design
energy
 
Description The tetrafunctionalized AB(3)-type porphyrin building blocks containing two different types of functional groups with N(4), N(3)O, N(3)S, and N(2)S(2) porphyrin cores were synthesized by following various synthetic routes. The AB(3)-type tetrafunctionalized N(4) Porphyrin building block was synthesized by a mixed condensation approach, the N(3)S and N(3)O porphyrin building blocks by a mono-ol method, and N(2)S(2) porphyrin building block by an unsymmetrical diol method. The tetrafunctionalized porphyrin building blocks were used to synthesize monofunctionalized porphyrin tetrads containing two different types of porphyrin subunits by coupling of 1 equiv of tetrafunctionalized N(4), N(3)O, N(3)S. and N(2)S(2) porphyrin building block with 3 equiv of monofunctionalized ZnN(4) porphyrin building block under mild copper-free Pd(0) coupling conditions. The monofunctionalized porphyrin tetrads were used further to synthesize unsymmetrical porphyrin pentads containing three different types of porphyrin subunits by coupling 1 equiv of monofunctionalized porphyrin tetrad with 1 equiv of monofunctionalized N(2)S(2) porphyrin building blocks under the same mild Pd(0) coupling conditions. The NMR, absorption, and electrochemical studies on porphyrin tetrads and porphyrin pentads indicated that the monomeric porphyrin subunits in tetrads and pentads retain their individual characteristic features and exhibit weak interaction among the porphyrin subunits. The steady state and time-resolved fluorescence studies support an efficient energy transfer from donor porphyrin subunit to acceptor porphyrin subunit in unsymmetrical porphyrin tetrads and porphyrin pentads.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-15T00:24:49Z
2011-12-26T12:49:08Z
2011-12-27T05:34:54Z
2011-07-15T00:24:49Z
2011-12-26T12:49:08Z
2011-12-27T05:34:54Z
2008
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 73(21), 8364-8375
0022-3263
http://dx.doi.org/10.1021/jo801455w
http://dspace.library.iitb.ac.in/xmlui/handle/10054/4104
http://hdl.handle.net/10054/4104
 
Language en