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Synthesis and Properties of Covalently Linked Trichromophore Systems
Author(s) -
Khan Tamanna K.,
Ravikanth Mangalampalli
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100952
Subject(s) - bodipy , porphyrin , chromophore , chemistry , covalent bond , photochemistry , fluorescence , fluorescence spectroscopy , combinatorial chemistry , organic chemistry , physics , quantum mechanics
Four covalently linked trichromophore systems containing a central boron dipyrromethene (BODIPY) unit connected to a porphyrin unit through the 3‐position and a core‐modified porphyrin or a porphyrin expanded through the 5‐position were synthesized by treating 3‐bromo‐5‐porphyrinyl BODIPY or 3‐bromo‐5‐rubyrinyl BODIPY with the corresponding hydroxy porphyrin or hydroxy‐expanded porphyrin in CHCl 3 at 60 °C. The compounds are freely soluble in common organic solvents and confirmed by mass spectrometry and 1D and 2D NMR spectroscopy techniques. The absorption and electrochemical studies support weak ground‐state interactions among the three chromophore units within the trichromophore systems. The fluorescence studies indicate that BODIPY emission is quenched to a significant degree in all trichromophore systems due to a transfer of energy to one or both macrocyclic units attached to the BODIPY chromophore.