Pyrene functionalized cyclotriphosphazene-based dyes: Synthesis, intramolecular excimer formation, and fluorescence receptor for the detection of nitro-aromatic compounds

Alidağı, Hüsnüye Ardıç; Tümay, Süreyya Oğuz; Şenocak, Ahmet; Yeşilot, Serkan

doi:10.1016/j.dyepig.2018.02.012

Cited by 47 publications

(15 citation statements)

References 59 publications

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“…However, fluorescence methods are currently displacing some conventional colorimetric (photometric) and radiometric methods in many applications, including chemical analysis and in biological detection . The advantages of fluorescence include high sensitivity that occasionally can reach the level of single molecules; flexibility in retrofitting various experimental setups; multiparametric encoding of information in the form of intensity, wavelength, anisotropy, and lifetime; and potential to respond to physicochemical attributes of the environment (temperature or pH). Many applications require relatively small molecules that exhibit large fluorescence quantum yields and additional photophysical features.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photophysics of a series of lipophilic phosphazene‐based fluorescent indicators

Selberg

Pagano

Tshepelevitsh

et al. 2019

J of Physical Organic Chem

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This work explores the 7-amino-4-(trifluoromethyl)coumarin backbone for designing lipophilic fluorescent pH indicators. Four novel fluorescent phosphazene bases with an advantageous combination of properties-high lipophilicity of both neutral and charged forms, lack of localized charges in the cations, and prominent spectral changes upon protonation/deprotonation-were synthesized using the Staudinger reaction. The molecular structures of the synthesized compounds were confirmed using attenuated total reflectance Fourier-transform infrared spectroscopy (ATR-FT-IR), nuclear magnetic resonance (NMR), and Fourier-transform ion-cyclotron resonance (FT-ICR)high-resolution mass spectrometry. The compounds were further characterized by ultraviolet-visible (UV-Vis) absorption and fluorescence emission spectra, lipophilicities (logP values) and pK a values in water and acetonitrile, as well as "biphasic" pK a values in the water/1-octanol solvent system. The bases could potentially be useful as working agents in optical pH sensors and acid-base indicators for lipophilic membranes.

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Section: Introductionmentioning

confidence: 99%

Synthesis and photophysics of a series of lipophilic phosphazene‐based fluorescent indicators

Selberg

Pagano

Tshepelevitsh

et al. 2019

J of Physical Organic Chem

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“…The adsorption capabilities of POFs for acetophenone are much higher than other materials due to their structural features: (1) The hydrophobic organic molecule (acetophenone) is more favorable for transport in the hydrophobic POF concave surface; (2) The high‐density aromatic fragments serve as binding sites for π–π interaction to enhance the affinity for phenyl substrates. [ 41 ]…”

Section: Methodsmentioning

confidence: 99%

Porous Organic Frameworks Featured by Distinct Confining Fields for the Selective Hydrogenation of Biomass‐Derived Ketones

et al. 2020

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opportunities, including facile separation and circulation of catalyst, easy purification of product, and continuous or multiple operations to address the tremendous requirements encountered in homogeneous catalysis. [7] One important characteristic is the confinement effect originating from the rigid cavity/channel of the solid platform. [8] In essence, as the pore size is adjusted to a reasonable range, the specific interaction between concave surface and substrate induces the subtle change of transition states and exerts great influence on the enantioselectivity in chiral synthesis. [9,10] It has been shown that some classical porous skeletons, such as inorganic solids (zeolites) and inorganic-organic hybrid solids (MOFs) have revealed a considerable substrate confinement effect. [11] However, the high proportion of inorganic constituents strongly disrupts the aromaticity of phenyl molecules due to the limitation of orbital spatial extension induced by the proximity of the pore walls. [12,13] The relatively low affinity results in an inadequate enantioselectivity for asymmetric catalysis, which cannot satisfy the strict standards for pure chiral substances put forth by the U.S. Food and Drug Administration. [12][13][14][15] As a novel type of crystalline solid, porous organic frameworks (POFs) have attracted a great deal of attention due to their promising applications in the fields of gas adsorption, [16] molecule separation, [17,18] optoelectronics, [19][20][21] etc. [22][23][24][25][26] In particular, POFs have shown great potential to serve as catalyst scaffolds due to their especially catalysis-friendly features, such as high permanent porosity, well-defined channels, and tuneable surfaces. [27][28][29][30][31][32][33] Their high proportions of conjugated components differ from the conventional porous matrices and will create specific affinities, such as hydrogen-π and π-π interactions for organic substances. Accordingly, the special confining reaction fields generated by POF channels may provide a new confinement effect for high-performance in asymmetric catalysis (Scheme 1).Herein, four 2D POF materials were synthesized with the same geometry and composition but with different pore diameters within the range of 1.2-2.9 nm by tuning the length of linkers (Figure 1). Through a facile post-modification, a chiralThe asymmetric hydrogenation of biomass-derived molecules for the preparation of single enantiomer compounds is an effective method to reduce the rapid consumption of fossil resources. Porous organic frameworks (POFs) with pure organic surfaces may provide unusual confinement effects for organic substrates in chiral catalysis. Here, a series of POF catalysts are designed with chiral active centers decorated into sharply defined onedimensional channels with diameters in the range of 1.2-2.9 nm. Due to the synergistic effect originating from the conjugated inner wall, the POF material (aperture size 2.4 nm) concentrates over 90% of aromatic species into the porous architecture, and its affinity is one...

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“…Recently, there has been substantial interest in cyclophosphazenes because they not only have an extensive stability range but they can also ensure excellent photophysical properties in combination with suitable fluorescent dyes, such as BODIPYs [15][16][17][18][19] and pyrene derivatives [20][21][22]. Hexachlorocyclotriphosphazene is a versatile starting scaffold for the synthesis of new compounds, as the chlorine groups attached to the phosphorus atoms are easily substituted by various nucleophiles to form reactive cyclotriphosphazenes.…”

Section: Introductionmentioning

confidence: 99%

Pyrene-BODIPY-substituted novel water-soluble cyclotriphosphazenes: synthesis, characterization, and photophysical properties

Çetindere¹,

Yeşilot²,

Kılıç³

2020

Turk J Chem

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In the present work, pyrene-boron-dipyrromethene (BODIPY)-substituted novel water-soluble cyclotriphosphazene derivatives (6 and 7) were synthesized by click reactions between a cyclotriphosphazene derivative with a hydrophilic glycol side group (2) and BODIPYs (4 and 5). All of the new compounds (2, 6, and 7) were characterized by Fourier-transform infrared and nuclear magnetic resonance spectroscopy, as well as mass spectrometry and elemental analysis. The photophysical properties of the BODIPY-substituted cyclotriphosphazenes (6 and 7) were investigated by UV-Vis and fluorescence emission spectroscopy in water and water/solvent mixtures. It was found that the target compounds were soluble in water and could be potential candidates as water-soluble fluorescent dyes for the desired applications.

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Pyrene functionalized cyclotriphosphazene-based dyes: Synthesis, intramolecular excimer formation, and fluorescence receptor for the detection of nitro-aromatic compounds

Cited by 47 publications

References 59 publications

Synthesis and photophysics of a series of lipophilic phosphazene‐based fluorescent indicators

Synthesis and photophysics of a series of lipophilic phosphazene‐based fluorescent indicators

Porous Organic Frameworks Featured by Distinct Confining Fields for the Selective Hydrogenation of Biomass‐Derived Ketones

Pyrene-BODIPY-substituted novel water-soluble cyclotriphosphazenes: synthesis, characterization, and photophysical properties

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