Publications by authors named "Parimal J Maliekal"

2 Publications

  • Page 1 of 1

Design and Development of Axially Chiral Bis(naphthofuran) Luminogens as Fluorescent Probes for Cell Imaging.

Chemistry 2021 Mar 25;27(17):5470-5482. Epub 2021 Feb 25.

Department of Speciality Chemicals Technology, Institute of Chemical Technology (ICT), Mumbai, 400019, India.

Designing chiral AIEgens without aggregation-induced emission (AIE)-active molecules externally tagged to the chiral scaffold remains a long-standing challenge for the scientific community. The inherent aggregation-caused quenching phenomenon associated with the axially chiral (R)-[1,1'-binaphthalene]-2,2'-diol ((R)-BINOL) scaffold, together with its marginal Stokes shift, limits its application as a chiral AIE-active material. Here, in our effort to design chiral luminogens, we have developed a design strategy in which 2-substituted furans, when appropriately fused with the BINOL scaffold, will generate solid-state emissive materials with high thermal and photostability as well as colour-tunable properties. The excellent biocompatibility, together with the high fluorescence quantum yield and large Stokes shift, of one of the luminogens stimulated us to investigate its cell-imaging potential. The luminogen was observed to be well internalised and uniformly dispersed within the cytoplasm of MDA-MB-231 cancer cells, showing high fluorescence intensity.
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March 2021

Synthesis of Concave and Vaulted 2-Pyran-Fused BINOLs and Corresponding [5] and [7]-Oxa-helicenoids: Regioselective Cascade-Concerted Route and DFT Studies.

J Org Chem 2020 Jun 4;85(12):7739-7747. Epub 2020 Jun 4.

Department of Chemistry, University of Mumbai, Vidyanagari, Santacruz(East), Mumbai 400098, India.

Synthesis of concave and vaulted 2-pyran-fused BINOLs has been achieved. A regioselective, path-breaking concerted cascade route allows the placement of six-membered heteroaromatic rings at the sterically crowded 7,8 and 7',8' positions of BINOL. DFT studies with relative energetics that support the kinetically controlled reaction pathway are preferred, matching the experimental results. The new BINOLs exhibit smaller dihedral angle than BINOL on the diol part; this structural feature can be an assisting factor for better ligation with metals in the metal-catalyzed reactions. Corresponding symmetric [5] and [7]-oxa-helicenoids have an overlapping, sterically crowded geometry.
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June 2020