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Phenylene-Bridged Core-Modified Planar Aromatic Octaphyrin: Aromaticity, Photophysical and Anion Receptor Properties.
- Source :
-
Chemistry - An Asian Journal . May2016, Vol. 11 Issue 9, p1447-1453. 7p. - Publication Year :
- 2016
-
Abstract
- The synthesis of a planar expanded meso porphyrin with an intramolecular para-phenylene-bridged core is reported. The planarity of the octaphyrin macrocycle was confirmed by single-crystal X-ray structural analysis, in which the bridged para-phenylene unit deviated by 27° from the mean macrocyclic plane. Spectroscopic analyses and theoretical calculations suggested that the macrocycle was Hückel aromatic and followed a major [34 π] single-conjugation pathway, which indicated that the bridging para-phenylene unit was not involved in the macrocyclic conjugation. Analysis of the photophysical properties of this system by steady-state absorption/fluorescence spectroscopy and transient absorption spectroscopy revealed moderate enhancement in the parameters of the octaphyrin as compared to its non-bridged octaphyrin congeners, which was attributed to the planarity and rigidity of the macrocycle as imposed by the bridging para-phenylene unit. Preliminary anion-binding studies revealed that the protonated macrocycle bound selectively with chloride ions through N−H⋅⋅⋅Cl hydrogen-bonding interactions. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 18614728
- Volume :
- 11
- Issue :
- 9
- Database :
- Academic Search Index
- Journal :
- Chemistry - An Asian Journal
- Publication Type :
- Academic Journal
- Accession number :
- 115247706
- Full Text :
- https://doi.org/10.1002/asia.201600177