Highly fluorescent materials derived from ortho-vanillin: Structural, photophysical electrochemical and theoretical studies

Poojary, Sachin; Acharya, Madhukara; Salam, Abdul Ajees Abdul; Kekuda, Dhananjaya; Nayek, Upendra; Kumar, Shankar; Adhikari, Airody Vasudeva; Sunil, Dhanya

doi:10.1016/j.molliq.2018.11.067

Cited by 14 publications

(4 citation statements)

References 56 publications

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“…The azo dye illustrated the highest dielectric constant among the three compounds. Thus, the fluorophoric property of the o‐vanillin derivatives endowed them with preferable candidates for electro‐optic devices 195 . Cyril et al.…”

Section: Applicationsmentioning

confidence: 99%

“…Thus, the fluorophoric property of the o-vanillin derivatives endowed them with preferable candidates for electro-optic devices. 195 Cyril et al also synthesized a bivanillin monomer via alkyl substitution and then polymerized with 1,4-benzene diamine or 2,7-carbazole 190 Copyright 2019, American Chemical Society diamine to produce polyazomethines. The polymers exhibited a good fluorescence effect ranging broadly from 400 up to 600 nm.…”

Section: Optoelectronic Materialsmentioning

confidence: 99%

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Bio‐renewable polymers based on lignin‐derived phenol monomers: Synthesis, applications, and perspectives

Yang

Ding

Puglia

et al. 2022

SusMat

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In recent decades, the continuous depletion of fossil fuels and the increasingly serious environmental issue have aroused wide attention on the development of biopolymers based on renewable biomass. Lignin is the second most abundant organic bio‐based macromolecule second to cellulose, and it can be widely found in plants. Furthermore, various phenol derivatives can be obtained by their depolymerization processes. The development of bio‐renewable polymeric materials originating from lignin‐derivative phenol monomers, such as vanillin, syringaldehyde, eugenol, vanillyl alcohol, vanillic acid, and ferulic acid, will not only valorize the bio‐sourced materials but also effectively reduce petroleum resource consumption and mitigate the environmental pollution. Therefore, an updated overview of the synthesis processes of these bio‐based polymers developed in the past decade, which includes both thermosets and thermoplastics such as epoxy, phenolic, polyimine, polybenzoxazine, polyurethane, and polyesters, are elucidated. In addition, the applications of these bio‐based polymers and their composites in flame‐retarded materials, degradable and reprocessable materials, dielectric materials, optoelectronic materials, as well as smart responsive materials are also intensively discussed. In line with the gradual development of synthesis technologies, we believe that derivatives of lignin will turn into one of the most promising materials to be considered for the preparation of high‐performance and functional bio‐based polymer materials.

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Section: Applicationsmentioning

confidence: 99%

Section: Optoelectronic Materialsmentioning

confidence: 99%

Bio‐renewable polymers based on lignin‐derived phenol monomers: Synthesis, applications, and perspectives

Yang

Ding

Puglia

et al. 2022

SusMat

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“…Furthermore, electrochemical studies were carried out to gather deeper insights into the electronic energy levels of SHB, which plays a vital role in device fabrication. 28 The values of HOMO and LUMO are associated with redox potentials, which indicates the hole/electron injection capabilities of organic compounds. The current versus voltage plot of SHB as depicted in Fig.…”

Section: Synthesis and Characterization Of Shbmentioning

confidence: 99%

Boronic Acid-Based n-Type Semiconductor for Electronic Device Application

Kagatikar

Sunil

Kekuda

et al. 2022

J. Electron. Mater.

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Electron transporting, or n-type, semiconductors can serve as charge-transport materials, and are ideal for use in organic electronic devices. Boron-based small organic molecules have garnered immense research attention as the heteroatom can effectively alter the electronic structures leading to excellent photophysical and electrochemical properties. A luminescent Schiff base (E)-(4-((2-(2-hydroxybenzoyl)hydrazono)methyl)phenyl)boronic acid (SHB) was prepared by a one-pot condensation reaction between salicyloyl hydrazide and formylphenylboronic acid. The synthesized molecule was chemically characterized by infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectrometry. The blue-emitting boronic acid-derived molecule displayed intramolecular charge transfer, high carrier concentration, good thermal stability, a reversible reduction tendency and formation of uniform amorphous thin films. A diode was successfully fabricated via a solution processing technique with an ideality factor of 7.76. Further, AC conductivity, dielectric constant, dielectric loss, and capacitance values in a frequency range of 10–1000 Hz were extracted from dielectric studies. The dielectric constant of SHB was found to be 9.71 with an AC conductivity of 6.34 × 10−9 Ω−1 cm−1 at 1000 Hz. Graphical Abstract

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“…Although both dyes allow convenient visualization of PAs in vacuoles in light microscopy, the images are neither quantitative nor sufficiently resolved to visualize cell-wall-bound PAs. Interestingly, both vanillin and DMACA have fluorogenic properties that have been extensively exploited in material sciences unrelated to plant biology ( Kaito et al., 1979 ; Katayama et al., 1987 ; Dryjanski et al., 1999 ; Singh and Mitra, 2008 ; Fritz et al., 2015 ; Poojary et al., 2019 ). DMACA fluorescence relies on an intramolecular charge transfer (ICT) mechanism, which results in substrate-specific excitation and emission spectra ( Singh and Mitra, 2008 ).…”

Section: Introductionmentioning

confidence: 99%

Fluorogenic properties of 4-dimethylaminocinnamaldehyde (DMACA) enable high resolution imaging of cell-wall-bound proanthocyanidins in plant root tissues

et al. 2023

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Proanthocyanidins (PAs) are polymeric phenolic compounds found in plants and used in many industrial applications. Despite strong evidence of herbivore and pathogen resistance-related properties of PAs, their in planta function is not fully understood. Determining the location and dynamics of PAs in plant tissues and cellular compartments is crucial to understand their mode of action. Such an approach requires microscopic localization with fluorescent dyes that specifically bind to PAs. Such dyes have hitherto been lacking. Here, we show that 4-dimethylaminocinnamaldehyde (DMACA) can be used as a PA-specific fluorescent dye that allows localization of PAs at high resolution in cell walls and inside cells using confocal microscopy, revealing features of previously unreported wall-bound PAs. We demonstrate several novel usages of DMACA as a fluorophore by taking advantage of its double staining compatibility with other fluorescent dyes. We illustrate the use of the dye alone and its co-localization with cell wall polymers in different Populus root tissues. The easy-to-use fluorescent staining method, together with its high photostability and compatibility with other fluorogenic dyes, makes DMACA a valuable tool for uncovering the biological function of PAs at a cellular level in plant tissues. DMACA can also be used in other plant tissues than roots, however care needs to be taken when tissues contain compounds that autofluoresce in the red spectral region which can be confounded with the PA-specific DMACA signal.

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Highly fluorescent materials derived from ortho-vanillin: Structural, photophysical electrochemical and theoretical studies

Cited by 14 publications

References 56 publications

Bio‐renewable polymers based on lignin‐derived phenol monomers: Synthesis, applications, and perspectives

Bio‐renewable polymers based on lignin‐derived phenol monomers: Synthesis, applications, and perspectives

Boronic Acid-Based n-Type Semiconductor for Electronic Device Application

Fluorogenic properties of 4-dimethylaminocinnamaldehyde (DMACA) enable high resolution imaging of cell-wall-bound proanthocyanidins in plant root tissues

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