Deep red emitting triphenylamine based coumarin-rhodamine hybrids with large Stokes shift and viscosity sensing: Synthesis, photophysical properties and DFT studies of their spirocyclic and open forms

Kothavale, Shantaram; Jadhav, Amol G.; Sekar, Nagaiyan

doi:10.1016/j.dyepig.2016.11.010

Cited by 48 publications

(31 citation statements)

References 53 publications

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“…[82] Recently,S ekarsg roup also reported the analogous coumarin-rhodamine dyes 170 (l em = 678 nm) and 171 (l em = 668 nm) that could be utilized as viscosity probes in visible and deep red regions. [20] Lins group demonstrated as ulfur dioxide-sensitive coumarinrhodamine fluorophore 172 (l em = 645 nm) that could act as aratiometric fluorescent probe with alarge emission shift and SNR. [83] In summary,c oumarin-rhodamine dyes with two excitation or emission wavelengths,h ave greatly facilitated the design of ratiometric fluorescent probes,thereby avoiding the deleterious effects that environmental factors (e.g., pH, temperature,a nd solvent polarity) can have on fluorescence analysis.…”

Section: Methodsmentioning

confidence: 99%

Hybrid Rhodamine Fluorophores in the Visible/NIR Region for Biological Imaging

et al. 2019

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Fluorophores and probes are invaluable for the visualization of the location and dynamics of gene expression, protein expression, and molecular interactions in complex living systems. Rhodamine dyes are often used as scaffolds in biological labeling and turn‐on fluorescence imaging. To date, their absorption and emission spectra have been expanded to cover the entire near‐infrared region (650–950 nm), which provides a more suitable optical window for monitoring biomolecular production, trafficking, and localization in real time. This review summarizes the development of rhodamine fluorophores since their discovery and provides strategies for modulating their absorption and emission spectra to generate specific bathochromic‐shifts. We also explain how larger Stokes shifts and dual‐emissions can be obtained from hybrid rhodamine dyes. These hybrid fluorophores can be classified into various categories based on structural features including the alkylation of amidogens, the substitution of the O atom of xanthene, and hybridization with other fluorophores.

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Section: Methodsmentioning

confidence: 99%

Hybrid Rhodamine Fluorophores in the Visible/NIR Region for Biological Imaging

et al. 2019

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“…From Table it observed that red shift in absorption spectra after increasing the solvent polarity suggest that intramolecular interaction between the donor and acceptor group in the ground state. Similarly, slight red shift in emission spectra observed with increasing the solvent polarity for both compounds 5 and 6 , exceptionally very high red shift observed in dichloromethane due to its highly acidic nature, suggesting that excited state is highly polar in polar solvents compared to in non‐polar solvents . Red shift in absorption and emission spectra are mainly influenced by the dipole‐dipole interaction, solute‐solvent interaction with the excited state of compounds.…”

Section: Resultsmentioning

confidence: 83%

Pyrene Based NLOphoric D‐π‐A‐π‐D Coumarin‐Chalcone and Their Red Emitting OBO Difluoride Complex: Synthesis, Solvatochromism, Z‐scan, and Detailed TD‐DFT Studies

Yadav

Erande

Sreenath³

et al. 2019

ChemistrySelect

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NLOphoric D-π-A-π-D coumarin chalcone 5 and their BF 2 complex 6 were designed, synthesized and characterized through Mass, 13 C-NMR, and 1 H-NMR analysis. Their Photophysical properties are extensively studied in solvents of different polarity. On BF 2 complexation of coumarin chalcone shows highly red shift in absorption and emission spectra compared to uncomplexed coumarin chalcone. Positive solvatochromism observed which is well supported by linear and multilinear regression analysis. For BF 2 complexed coumarinchalcone 6 the solvent dipolarity (C SdP ) is the main factor responsible for slightly red shift in absorption spectra, and also for the highly red-shift in emission spectra. Frontier molecular orbital, molecular electrostatic potential and Generalized Mulliken-Hush analysis revealed intramolecular charge transfer in these compounds. Nonlinear optical (NLO) properties for compounds 5 and 6 were studied by solvatochromic and computational method. The linear polarizability (α), first-order hyperpolarizability (β) and second-order hyperpolarizability (γ) of compounds were studied by the time dependent density functional theory using three different functionals namely B3LYP, BHHLYP and CAMÀ B3LYP with the 6-31 G (d) basis set. BF 2 complexed compound 6, show higher values for α e + α v as well as β e + β v compared to compound 5. Third order nonlinear optical susceptibility (χ (3) ) of these compounds obtained by Zscan analysis. Third-order (χ (3) ) non-linear optical properties of BF 2 complexed coumarin-chalcone 6 were observed to be several times higher than those of the uncomplexed coumarinchalcone 5 these justify the design approach.[a] S.

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“…Various approaches have been attempted to solve these problems. The introduction of aryl, alkynyl, styryl, or heteroatom substituents is an effective strategy to expand the π‐system to achieve red shifting in the absorption bands . Shen and co‐workers introduced thiophene substituents to BODIPY for prolonged π‐conjugation.…”

Section: Current Organic Dyes For Nanomedicinementioning

confidence: 99%

Organic Dye Based Nanoparticles for Cancer Phototheranostics

Cai

Huang

et al. 2018

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Phototheranostics, which simultaneously combines photodynamic and/or photothermal therapy with deep-tissue diagnostic imaging, is a promising strategy for the diagnosis and treatment of cancers. Organic dyes with the merits of strong near-infrared absorbance, high photo-to-radical and/or photothermal conversion efficiency, great biocompatibility, ready chemical structure fine-tuning capability, and easy metabolism, have been demonstrated as attractive candidates for clinical phototheranostics. These organic dyes can be further designed and fabricated into nanoparticles (NPs) using various strategies. Compared to free molecules, these NPs can be equipped with multiple synergistic functions and show longer lifetime in blood circulation and passive tumor-targeting property via the enhanced permeability and retention effect. In this article, the recent progress of organic dye-based NPs for cancer phototheranostic applications is summarized, which extends the anticancer arsenal and holds promise for clinical uses in the near future.

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Deep red emitting triphenylamine based coumarin-rhodamine hybrids with large Stokes shift and viscosity sensing: Synthesis, photophysical properties and DFT studies of their spirocyclic and open forms

Cited by 48 publications

References 53 publications

Hybrid Rhodamine Fluorophores in the Visible/NIR Region for Biological Imaging

Hybrid Rhodamine Fluorophores in the Visible/NIR Region for Biological Imaging

Pyrene Based NLOphoric D‐π‐A‐π‐D Coumarin‐Chalcone and Their Red Emitting OBO Difluoride Complex: Synthesis, Solvatochromism, Z‐scan, and Detailed TD‐DFT Studies

Organic Dye Based Nanoparticles for Cancer Phototheranostics

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