Synthesis and Polarity-Sensitive Fluorescent Properties of a Novel Water-Soluble Polycyclic Aromatic Hydrocarbon (PAH)

2020 ◽  
Author(s):  
Samantha Dena Sweet ◽  
Drew Robert Coulson ◽  
Jean-Benoît Giguère ◽  
Jean-Francois Morin ◽  
Brian D. Wagner
Keyword(s):  
Aqueous Solution ◽  
Fluorescence Probe ◽  
Water Soluble ◽  
Sensitivity Factor ◽  
Side Chains ◽  
Fluorescent Properties ◽  
Visible Absorption ◽  
Polycyclic Aromatic Compound ◽  
Polycyclic Aromatic ◽  
Polarity Sensitive

We report the successful synthesis and spectroscopic characterization of a novel, water soluble anthanthrene-based derivative, 6,12-bis(TEG)anthanthrene 3. The presence of the two long ethylene glycol side chains gives this large, 6-membered polycyclic aromatic compound a high aqueous solubility. It exhibits UV-visible absorption properties similar to those of anthanthrene itself, indicating that the side chains do not have a significant effect on the electronic structure of the central chromophore. The compound exhibits strong, polarity-sensitive fluorescence in aqueous solution in the blue-green region of the spectrum, with a fluorescence quantum yield of 0.13, and a Polarity Sensitivity Factor (PSF) of 2.0. The utility of this new fluorescent molecule as a probe of supramolecular complexation was demonstrated by its inclusion into the molecular host hydroxypropyl-β-cyclodextrin in aqueous solution. Strictly 1:1 inclusion was observed, with a moderately strong binding constant K of 650 M-1. This new fluorescence probe has significant potential applications in fluorescence-based studies of aqueous biochemical and supramolecular systems.

A Three-Dimensional Tetraphenylethylene-Based Fluorescence Covalent Organic Framework for Molecular Recognition

2020 ◽  
Author(s):  
Junxia Ren ◽  
Yaozu Liu ◽  
Xin Zhu ◽  
Yangyang Pan ◽  
Yujie Wang ◽  
...  
Keyword(s):  
Molecular Recognition ◽  
Fluorescence Probe ◽  
Three Dimensional ◽  
Hazardous Substances ◽  
Covalent Organic Framework ◽  
Highly Sensitive ◽  
Volatile Organic ◽  
Polycyclic Aromatic ◽  
Better Than ◽  
Organic Framework

<p><a></a><a></a><a></a><a></a><a></a><a></a><a></a><a>The development of highly-sensitive recognition of </a><a></a><a></a><a></a><a></a><a>hazardous </a>chemicals, such as volatile organic compounds (VOCs) and polycyclic aromatic hydrocarbons (PAHs), is of significant importance because of their widespread social concerns related to environment and human health. Here, we report a three-dimensional (3D) covalent organic framework (COF, termed JUC-555) bearing tetraphenylethylene (TPE) side chains as an aggregation-induced emission (AIE) fluorescence probe for sensitive molecular recognition.<a></a><a> </a>Due to the rotational restriction of TPE rotors in highly interpenetrated framework after inclusion of dimethylformamide (DMF), JUC-555 shows impressive AIE-based strong fluorescence. Meanwhile, owing to the large pore size (11.4 Å) and suitable intermolecular distance of aligned TPE (7.2 Å) in JUC-555, the obtained material demonstrates an excellent performance in the molecular recognition of hazardous chemicals, e.g., nitroaromatic explosives, PAHs, and even thiophene compounds, via a fluorescent quenching mechanism. The quenching constant (<i>K</i><sub>SV</sub>) is two orders of magnitude better than those of other fluorescence-based porous materials reported to date. This research thus opens 3D functionalized COFs as a promising identification tool for environmentally hazardous substances.</p>

Enantioselective Recognition of Chiral Guests by the Water-Soluble Chiral Keplerate {Mo132} Spherical Capsule with 30 Inner Lactate Ligands

2019 ◽  
Author(s):  
Nancy Watfa ◽  
Weimin Xuan ◽  
Zoe Sinclair ◽  
Robert Pow ◽  
Yousef Abul-Haija ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Chiral Recognition ◽  
Association Constants ◽  
Water Soluble ◽  
Enantioselective Recognition ◽  
H Nmr ◽  
Dosy Nmr ◽  
Spherical Capsule ◽  
Surface Pores ◽  
Guest Chemistry

Investigations of chiral host guest chemistry are important to explore recognition in confined environments. Here, by synthesizing water-soluble chiral porous nanocapsule based on the inorganic metal-oxo Keplerate-type cluster, {Mo<sub>132</sub>} with chiral lactate ligands with the composition [Mo<sub>132</sub>O<sub>372</sub>(H<sub>2</sub>O)<sub>72</sub>(<i>x-</i>Lactate)<sub>30</sub>]<sup>42-</sup> (<i>x</i> = D or L), it was possible to study the interaction with a chiral guest, L/D-carnitine and (<i>R</i>/<i>S</i>)-2-butanol in aqueous solution. The enantioselective recognition was studied by quantitative <sup>1</sup>H NMR and <sup>1</sup>H DOSY NMR which highlighted that the chiral recognition is regulated by two distinct sites. Differences in the association constants (K) of L- and D-carnitine, which, due to their charge, are generally restricted from entering the interior of the host, are observed, indicating that their recognition predominantly occurs at the surface pores of the structure. Conversely, a larger difference in association constants (K<i><sub>S</sub></i>/K<i><sub>R</sub></i> = 3) is observed for recognition within the capsule interior of (<i>R</i>)- and (<i>S</i>)-2-butanol.

scholarly journals Sulfobetaine Cryogels for Preferential Adsorption of Methyl Orange from Mixed Dye Solutions

Polymers ◽  
2021 ◽  
Vol 13 (2) ◽  
pp. 208
Author(s):  
Ramona B. J. Ihlenburg ◽  
Anne-Catherine Lehnen ◽  
Joachim Koetz ◽  
Andreas Taubert
Keyword(s):  
Aqueous Solution ◽  
Methylene Blue ◽  
Methyl Orange ◽  
Dye Removal ◽  
Selective Adsorption ◽  
Water Soluble ◽  
Organic Substances ◽  
Preferential Adsorption ◽  
Dimethyl Ammonium ◽  
Dye Solutions

New cryogels for selective dye removal from aqueous solution were prepared by free radical polymerization from the highly water-soluble crosslinker N,N,N’,N’-tetramethyl-N,N’-bis(2-ethylmethacrylate)-propyl-1,3-diammonium dibromide and the sulfobetaine monomer 2-(N-3-sulfopropyl-N,N-dimethyl ammonium)ethyl methacrylate. The resulting white and opaque cryogels have micrometer sized pores with a smaller substructure. They adsorb methyl orange (MO) but not methylene blue (MB) from aqueous solution. Mixtures of MO and MB can be separated through selective adsorption of the MO to the cryogels while the MB remains in solution. The resulting cryogels are thus candidates for the removal of hazardous organic substances, as exemplified by MO and MB, from water. Clearly, it is possible that the cryogels are also potentially interesting for removal of other compounds such as pharmaceuticals or pesticides, but this must be investigated further.

scholarly journals Development of A New Water-soluble Fluorescence Probe for Hypochlorous Acid Detection in Drinking Water

2021 ◽  
pp. 100027
Author(s):  
Haoyuan Yin ◽  
Haijun Chi ◽  
Zhuye Shang ◽  
Ali Qaitoon ◽  
Jianfei Yu ◽  
...  
Keyword(s):  
Drinking Water ◽  
Hypochlorous Acid ◽  
Fluorescence Probe ◽  
Water Soluble

scholarly journals Water-soluble β-aminobisulfonate building blocks for pH and Cu2+ indicators

RSC Advances ◽  
2016 ◽  
Vol 6 (88) ◽  
pp. 84712-84721 ◽  
Author(s):  
Maria A. Cardona ◽  
Marina Kveder ◽  
Ulrich Baisch ◽  
Michael R. Probert ◽  
David C. Magri
Keyword(s):  
Nmr Spectroscopy ◽  
Building Blocks ◽  
Water Soluble ◽  
Visible Absorption ◽  
H Nmr ◽  
Uv Visible

Two phenyl β-aminobisulfonate ligands characterised by UV-visible absorption, EPR and 1H NMR spectroscopy exhibit evidence for binding with Cu2+ in water and methanol.

The reactions of linear conjugated diynes with Dicarbonyl(η-cyclopentadienyl)- cobalt and -rhodium

1975 ◽  
Vol 28 (2) ◽  
pp. 285 ◽  
Author(s):  
RS Dickson ◽  
LJ Michel
Keyword(s):  
Thermal Degradation ◽  
Aromatic Compound ◽  
Substituted Benzenes ◽  
Polycyclic Aromatic Compound ◽  
Organic Products ◽  
Polycyclic Aromatic ◽  
Alkyne Complexes ◽  
Conjugated Diynes

The reactions of (η-C5H5)Co(CO)2 with the diynes hexa-2,4-diyne and 1,4- diphenylbutadiyne give three isomers of the cyclopentadienone complexes (C5H5)Co[(RC2C2R)2CO], R = Me or Ph, and two isomers of the tris-alkyne complexes (C5H5)2Co2(RC2C2R)3CO, R = Me or Ph. Organic products of formula (RC2C2R)3, R = Me or Ph, (MeC2C2Me)5, and (PhC2C2Ph)3CO have been isolated also. Two isomers of (RC2C2R), were separated and were identified as the 1,2,4-(R)3-3,5,6-(C2R)3- and the 1,3,5-(R)3-2,4,6-(C2R)3-benzenes. The compound (PhC2C2Ph)3CO is believed to be tris(phenylethynly)triphenylcycloheptatrienone, and (MeC2C2Me)5 is probably a polycyclic aromatic compound. Thermal degradation of the complexes (C5H5)2CO2(RC2C2R)3CO gives the substituted benzenes (RC2C2R)3. ��� The reaction of (η-C5H5)Rh(CO)2 and hexa-2,4-diyne gives the cyclopentadienone complex(C5H5)Rh[(MeC2C2Me)2CO] and the cycloheptatrienone complex (C5H5)Rh[(MeC2C2Me)3CO].Two isomers of the substituted benzene (MeC2C2Me)3 were obtained also.

Sign in / Sign up

Export Citation Format

Share Document