Facile synthesis, characterisation and anti‐inflammatory activities of ferrocenyl ester derivatives of 4‐arylidene‐5‐imidazolinones

Shinde, Dilip N.; Trivedi, Rajiv; Krishna, Narra Vamsi; Giribabu, Lingamallu; Sridhar, Balasubramanian; Rathod, Balaji; Prakasham, R. S.

doi:10.1002/aoc.4021

Cited by 4 publications

(1 citation statement)

References 56 publications

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“…The excited state intramolecular proton transfer (ESIPT) mechanism for the 2‐hydroxy derivatives of the GFP chromophore was hypothesised earlier [49–56] . Therefore, we investigated the effect of the position of the hydroxyl group on the fluorescence properties.…”

Section: Resultsmentioning

confidence: 92%

Synthesis and Fluorescence Mechanism of the Aminoimidazolone Analogues of the Green Fluorescent Protein: Towards Advanced Dyes with Enhanced Stokes Shift, Quantum Yield and Two‐Photon Absorption

et al. 2021

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Novel small‐molecular analogues the green fluorescence protein (GFP) chromophore were synthesised to expand and improve this fluorophore family and to deepen the understanding of their fluorescence mechanism. The introduction of an aminophenyl substituent and the repositioning of the hydroxyl group, to enable strong intramolecular hydrogen bonding, not only enhanced fluorescence emission but also resulted in an increased Stokes shift and a considerable redshift. Experimental and computational results described dual fluorescence involving both excited‐state intramolecular proton transfer and internal charge transfer (ESIPT‐ICT) mechanisms. Screening of the pH and the solvent medium revealed a complicated equilibrium involving hydrogen bonding, protonation and deprotonation that influences the absorption and emission spectra. Further improvement of the photophysical properties via the systematic variation of dialkylamino substituents at a single position of the chromophore led to a two‐orders of magnitude enhancement in the quantum yields. In addition, the novel compounds also have significant two‐photon absorption, which widens the possibilities for applications in the field of bioimaging.

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Section: Resultsmentioning

confidence: 92%

Synthesis and Fluorescence Mechanism of the Aminoimidazolone Analogues of the Green Fluorescent Protein: Towards Advanced Dyes with Enhanced Stokes Shift, Quantum Yield and Two‐Photon Absorption

et al. 2021

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2,4‐Thiazolidinedione as a Bioactive Linker for Ferrocenyl Sugar–Triazole Conjugates: Synthesis, Characterization and Biological Properties

et al. 2018

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A new series of ferrocenyl sugar-triazole conjugates, derived from D-xylose, D-ribose and D-galactose, linked by a 2,4thiazolidinedione moiety, has been prepared. Facile 1,3-dipolar-Huisgen coupling reactions of the respective sugar azides with the ferrocenyl 2,4-thiazolidinedione alkyne units give the corresponding conjugates. These conjugates have been characterized by various spectroscopic techniques, including UV/Vis [a] Synthesis and CharacterizationThe compound 2,4-thiazolidinedione was prepared by a literature method [26] and was condensed with ferrocene-carboxaldehyde 1, under Knoevenagel conditions, to form compound 2, Scheme 1. Synthesis of ferrocenyl 2,4-thiaolidinedione alkyne.Scheme 2. Synthesis of ferrocenyl 2,4-thiazolidinedione sugar-triazole conjugates 5a-g.Eur. J. Inorg. Chem. 2018, 1571-1580 www.eurjic.org

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Green fluorescent protein inspired fluorophores

Kong

Wang

et al. 2020

Advances in Colloid and Interface Science

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Facile synthesis, characterisation and anti‐inflammatory activities of ferrocenyl ester derivatives of 4‐arylidene‐5‐imidazolinones

Cited by 4 publications

References 56 publications

Synthesis and Fluorescence Mechanism of the Aminoimidazolone Analogues of the Green Fluorescent Protein: Towards Advanced Dyes with Enhanced Stokes Shift, Quantum Yield and Two‐Photon Absorption

Synthesis and Fluorescence Mechanism of the Aminoimidazolone Analogues of the Green Fluorescent Protein: Towards Advanced Dyes with Enhanced Stokes Shift, Quantum Yield and Two‐Photon Absorption

2,4‐Thiazolidinedione as a Bioactive Linker for Ferrocenyl Sugar–Triazole Conjugates: Synthesis, Characterization and Biological Properties

Green fluorescent protein inspired fluorophores

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