4.5 Article

Rhodamine tethered 1,1′-unsymmetrical ferrocene functionalization: Metal sensing, cell imaging and logic gate properties

Journal

JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 948, Issue -, Pages -

Publisher

ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2021.121922

Keywords

Solvent free; Ferrocenyl; Unsymmetrical; Rice husk ash; Bioimaging; Fluorescence

Funding

  1. Council of Scientific and Industrial Research (CSIR), India [01(2948)/18/EMRII]

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Selective functionalization of ferrocenyl species with fluorescent active rhodamine moiety using a solvent free solid state method led to the synthesis of 1,1'- unsymmetrical ferrocene based turn-on fluorescent hydrazone molecular system. The unsymmetrical molecular system was structurally characterized by single crystal X-ray diffraction crystallography and showed significant intracellular metal recognition and imaging characteristics. Molecular logic gate property was also studied using the fluorometric molecular compound for INHIBIT, OR and combinational logic operations.
Selective funtionalization of ferrocenyl species with fluorescent active rhodamine moiety using a solvent free solid state method led to the synthesis of 1,1'- unsymmetrical ferrocene based turn-on fluorescent hydrazone molecular system, 1,1'-[CH3C(O)(eta(5)-C5H4)Fe{(eta(5)-C5H4)C(CH3)=N-NC(O)-X}], (X = Rhodamine-6G) (1) and 1,1'-[HC(O)(eta(5)-C5H4)Fe{(eta(5)-C5H4)C(H)=N-NC(O)-X}], (X = Rhodamine-6G (2), Rhodamine-B (3)). The unsymmetrical molecular system was structurally characterized by single crystal X-ray diffraction crystallography. Their fluorescence based signaling and sensing behavior has been explored with metal cations to observe remarkable fluorescence enhancement capabilities in the intracellular matrix. The interaction behavior of the unsymmetrical ferrocene based rhodaminyl organometallic receptor has been established by DFT study and spectroscopic analysis. The study showed some significant intracellular metal recognition and imaging characteristics to understand their potential in applications related to bioimaging of heavy metal ions. Molecular logic Gate property was also studied corresponding to INHIBIT, OR and a combinational logic operations using the fluorometric molecular compound. (C) 2021 Elsevier B.V. All rights reserved.

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