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- Title
Synthesis and properties of Oxasmaragdyrins containing one Five-membered Heterocycle at Meso-position.
- Authors
UMASEKHAR, BOORUGA; SAMANTA, PALLAB; CHATTERJEE, TAMAL; RAVIKANTH, MANGALAMPALLI
- Abstract
The oxasmaragdyrins containing one five membered heterocycle such as pyrrole, thiophene and furan in place of one of the meso-phenyl group were synthesized by acid-catalyzed oxidative coupling reaction of meso-heterocycle substituted dipyrromethane with 16-oxatripyrrane in the presence of catalytic amount of trifluoroacetic acid followed by oxidation with DDQ. The smaragdyrin macrocycles containing one five-membered heterocycle at meso-position were characterized by HR-MS and detailed 1D and 2D NMR studies. The absorption and fluorescence studies revealed that the presence of five membered heterocycle at meso-position of smaragdyrin resulted in bathochromic shifts in absorption and emission bands with slight reduction in quantum yields compared to smraragdyrin macrocycle containing six membered meso-phenyl groups. The electrochemical studies revealed that the meso-heterocycle smaragdyrins are electron deficient compared to meso-phenyl smaragdyrins.
- Subjects
HETEROCYCLIC compounds synthesis; MESO compounds; PHENYL group; DIPYRROMETHANES; TRIFLUOROACETIC acid; NUCLEAR magnetic resonance spectroscopy
- Publication
Journal of Chemical Sciences, 2016, Vol 128, Issue 11, p1709
- ISSN
0974-3626
- Publication type
Article
- DOI
10.1007/s12039-016-1178-x