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Synthesis and Studies of Covalently Linked Porphyrin‐Expanded Heteroporphyrin Dyads
Author(s) -
Rajeswara Rao M.,
Ravikanth M.
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.201001482
Subject(s) - porphyrin , chemistry , photochemistry , fluorescence , covalent bond , combinatorial chemistry , organic chemistry , physics , quantum mechanics
Mono‐functionalized core‐modified sapphyrin (with a N 2 S 3 core) and smaragdyrin (with a N 4 O core) containing a meso ‐iodophenyl functional group were synthesized by following a [3+2] condensation approach using appropriate precursors. The mono‐functionalized sapphyrin and smaragdyrin building blocks were used to synthesize the first examples of diphenyl ethyne bridged porphyrin–sapphyrin and porphyrin/Zn II porphyrin–smaragdyrin dyads under mild Pd 0 ‐coupling conditions. The dyads are freely soluble in common organic solvents and were characterized by various spectroscopic techniques. Photophysical studies indicated the possibility of energy transfer from the porphyrin/Zn II porphyrin sub‐unit to the smaragdyrin sub‐unit in porphyrin/Zn II porphyrin–smaragdyrin dyads. The potential of these dyads as fluorescent sensors for anions was explored. The studies indicated that the porphyrin–sapphyrin dyad cannot be used as fluorescent sensors, whereas the porphyrin–smaragdyrin dyad was suitable.