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A3-type Star Stilbene and Cyanostilbene molecules: Synthesis, Fluorescent properties and bio-imaging application

Abstract

Abstract Stilbene and cynanostilbene based new A3-type star molecules containing blocked isocyanate functionalities were synthesized and structures of the compounds were confirmed. The photophysical properties of the molecules were studied using absorption and fluorescenc spectroscopic techniques. Intramolecular charge transfer absorption of star stilbene and star cyanostilbene was found at 370 nm and 430 nm respectively. On excitation at ICT absorption, the stilbene and cyanostilbene star molecules showed fluorescence with maximum in the region of 443-470 nm and 498-540 nm respectively. On increasing the solvent polarity, fluorescence maximum of both of the star molecules showed bathochromic shift with increase in the Stoke shift. The change in dipole moment on excitation was calculated from the Lippert-Mattaga plot and found that the molecules were more polar in excited state. Fluorescence quantum yield and fluorescence lifetime of these molecules were determined; the average lifetime value for stilbene based molecule was found to be 2.05 ns and this value for cyanostilbene based molecule was found to be 0.66 ns. Star cyanostilbene showed aggregation-induced emission; it displayed lower wavelength emission in pure THF but it exhibited emission with red shift in water/THF binary mixture. These molecules also showed considerably low band gap energy between highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO); the values were in the range of 2.55 eV - 2.87 eV. Based on the photophysical studies, the molecule containing cyanostilbene unit was used as a fluorophore for bio-imaging application in Zebra fish eggs as modal and the results were found excellent.

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Publication details

The article was received on 07 Feb 2018, accepted on 16 Apr 2018 and first published on 03 May 2018


Article type: Paper
DOI: 10.1039/C8NJ00676H
Citation: New J. Chem., 2018, Accepted Manuscript
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    A3-type Star Stilbene and Cyanostilbene molecules: Synthesis, Fluorescent properties and bio-imaging application

    G. A, K. Ramamurthy, S. mamangam, S. Chellappan and S. A. Nasar, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ00676H

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