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Synthesis and properties of Oxasmaragdyrins containing one Five-membered Heterocycle at Meso-position

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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.

Synthesis and properties of mono meso-heterocyclic substituted Oxasmaragdyrins are reported.

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Acknowledgements

We thank Department of Science and Technology, Govt. of India for funding the project. US thanks UGC for JRF fellowship.

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Supplementary Information (SI)

Supplementary data (mass spectra and NMR spectra) associated with the article are available at www.ias.ac.in/chemsci.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, Maharashtra, 400 076, India

    BOORUGA UMASEKHAR, PALLAB SAMANTA, TAMAL CHATTERJEE & MANGALAMPALLI RAVIKANTH

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  1. BOORUGA UMASEKHAR
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  2. PALLAB SAMANTA
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  3. TAMAL CHATTERJEE
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  4. MANGALAMPALLI RAVIKANTH
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Correspondence to MANGALAMPALLI RAVIKANTH.

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Dedicated to Professor Tavarekere K Chandrashekar on the occasion of his 60th birthday

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UMASEKHAR, B., SAMANTA, P., CHATTERJEE, T. et al. Synthesis and properties of Oxasmaragdyrins containing one Five-membered Heterocycle at Meso-position. J Chem Sci 128, 1709–1715 (2016). https://doi.org/10.1007/s12039-016-1178-x

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  • DOI: https://doi.org/10.1007/s12039-016-1178-x

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