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Tuning of intermolecular interactions results in packing diversity in imidazolin-5-ones

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Abstract

Crystal structures of four green fluorescent protein (GFP) chromophore analogues with different packing interactions could be tuned by appropriate substitutions around the imidazolin-5-one ring are reported here. Compound 1 was crystallized from tetrahydrofuran at room temperature while compounds 2-4 have been crystallized from a mixture of methanol and dichloromethane in 3:1 ratio. Molecule 1, 2 and 3 crystallized in monoclinic lattice while molecule 4 preferred to crystallize in a triclinic crystal system. The crystal packing of these molecules was stabilized by C-H…π stacking and C-H… O type of supramolecular interactions. The results reveal that packing diversity can be easily accomplished in these molecules by tuning the substituents around the imidazolin-5-one ring. Photophysical studies also reveal that all have good quantum yield and fluoresce typically in red region due to presence of electron donating groups around the imidazolin-5-one ring.

Crystal structures of four green fluorescence protein (GFP) chromophore analogues are reported. Stabilization through packing and packing diversity in crystals are achieved by modulating supramolecular interaction by varying the substituents.

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Acknowledgements

A.S. and B.K.R. thank UGC and CSIR, respectively for junior and senior research fellowships (JRF & SRF). Compound 1 was synthesized and solved by BKR and is reported previously in his PhD thesis.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208 016, India

    ASHISH SINGH, BASANTA KUMAR RAJBONGSHI & GURUNATH RAMANATHAN

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  1. ASHISH SINGH
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  2. BASANTA KUMAR RAJBONGSHI
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Correspondence to GURUNATH RAMANATHAN.

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Supplementary Information

Supplementary material contains all 1H and 13C spectra, cif and cif check files. The final CIF files were deposited at Cambridge Crystallographic Data Centre and the CCDC numbers are reported in the manuscript. Figures S1–S4 can be seen at www.ias.ac.in/chemsci.

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SINGH, A., RAJBONGSHI, B.K. & RAMANATHAN, G. Tuning of intermolecular interactions results in packing diversity in imidazolin-5-ones. J Chem Sci 126, 1275–1284 (2014). https://doi.org/10.1007/s12039-014-0689-6

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