The derivation and characterization of quinine charge-transfer complexes with inorganic and organic acceptors in liquid and solid form

Adam, Abdel Majid A.; Saad, Hosam A.; Refat, Moamen S.; Hegab, Mohamed S.; Al‐Hazmi, Ghaferah H.; Alsuhaibani, Amnah Mohammed; Mohamed, Hany M.

doi:10.1016/j.molliq.2022.119206

Cited by 4 publications

(3 citation statements)

References 126 publications

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“…Diastereomeric pairs of cinchonidine ( CD )/cinchonine ( CN ) and quinidine ( QD )/quinine ( QN ) collectively termed as “cinchona alkaloids” are a class of natural chiral molecules derived from cinchona bark and have shown a wide range of applications in the catalysis and treatment of malaria. − However, the chiral properties of cinchona alkaloids in luminescence have been seldom studied, mainly due to their weak emissions. , The molecules of cinchona alkaloids contain four parts: quinuclidine base, quinoline ring, hydroxy-substituted stereogenic linkage with polychiral carbons, and vinyl group (Figure a). The N atom of the quinuclidine moiety can interact with other molecules through hydrogen bonding, and the conjugated quinoline unit with π-electron and N-lone pair electron may promote the photoactivities and intermolecular interactions. , The stereogenic configurations of these chiral C atoms could define the sense of enantioselectivity in emission, while the vinyl group will react with other vinyl monomers in forming copolymers.…”

Section: Resultsmentioning

confidence: 99%

High-Quality Circularly Polarized Organic Afterglow from Nonconjugated Amorphous Chiral Copolymers

Zhang,

Jin,

Wang

et al. 2023

ACS Appl. Mater. Interfaces

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Organic materials featuring circularly polarized luminescence (CPL) and/or afterglow emission represent an active research frontier with promising applications in various fields, but the achievement of high-performance CPL organic afterglow (CPOA) remains a huge challenge due to the intrinsic contradictions between the luminescent lifetime/dissymmetry factor (g lum) and phosphorescent quantum efficiency (PhQY). Herein, we report a simple and universal approach to design efficient CPOA from amorphous copolymers by incorporating chiral chromophores into a nonconjugated clusterization-triggered emissive polymer with plenty of hydron-bonding interactions, followed by aggregation engineering using water dissolution and evaporation. With this chiral copolymerization and aggregation engineering (CCAE) strategy, high-performance CPOA polymers with PhQYs of up to 6.32%, ultralong lifetimes of over 650 ms, g lum values of 3.54 × 10–3, and the highest figure-of-merit were achieved at room temperature. Given the impressive CPOA performance of these polymers, the applications in multilevel data anticounterfeiting and reversible displays with high stability were demonstrated. These findings through the CCAE strategy to overcome the inherent restraints of CPOA materials lay the foundation for the development of amorphous polymers with superior CPOA, significantly expanding the understanding of CPL and the design of organic afterglow materials.

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Section: Resultsmentioning

confidence: 99%

High-Quality Circularly Polarized Organic Afterglow from Nonconjugated Amorphous Chiral Copolymers

Zhang,

Jin,

Wang

et al. 2023

ACS Appl. Mater. Interfaces

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“…From this experiment, it follows that antimalarial drugs really work as antiviral drugs in the case of coronavirus infection. However, many researchers are opposed to such a treatment regimen for COVID-19, and even make claims that antimalarial drugs not only do not have an effective effect, but are also harmful to the body 29 . The Wor ld Health Organisation (2021) does not recommend hydroxychloroquine for the treatment of COVID-19 30 .…”

Section: Discussionmentioning

confidence: 99%

Synthesis and structure of new modified derivatives based on the quinine molecule and their biological activity

Zhasymbekova

Nurmaganbetov

2023

Polish Journal of Chemical Technology

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The relevance of the subject matter is conditioned by the constantly growing need to meet human needs in the field of medicine, in particular, the search, study, and further introduction of new types of medicines into practical use. The purpose of this study is to investigate the synthesis of modified quinine alkaloid derivatives, and their structure, to identify the properties and biological activity of antimalarial drugs based on quinine molecules, and to structure the general data of these substances. The leading approach is the analysis of the synthesis of quinine derivatives, their chemical and physical properties, and their ability to exert a medicinal effect. The abstracting method allows structuring alkaloid derivatives and establishing a general relationship between the structural configuration of molecules and their impact on human health in a number of related derivatives. The study identifies the main antimalarial drugs based on quinine molecules, including a comparative analysis of their effectiveness and overall biological activity.

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“…With this local excitation, PRT absorbs the light around 400−430 nm and exhibits a yellow color. However, in PRT salts, for example, PRT-BSA, the lone pair electrons, is provided by the BSA anion instead of PRT (Figure 15b), called charge-transfer excitation, 45 because of which the energy gap between the HOMO and LUMO orbital decreases notably so that the absorption wavelength has a typical red shift, and the color of the salts appears to be more orangish or reddish than that of PRT (Table 9). The molecular orbital figures of other PRT salts can be found in the Supporting Information (Figure S13).…”

Section: Idr Testmentioning

confidence: 99%

Colorful Prothionamide Salt Forms with Enhancement in Water Solubility and Dissolution Behavior

Jiang

Hong

et al. 2023

Crystal Growth & Design

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Prothionamide (PRT) is used as an alternative to some first-line drugs in the treatment of multi drug-resistant tuberculosis. Suffering from its extremely low water solubility and physiological constraints, the clinical use of PRT is restricted. The crystal engineering technique has been proven to be a good way to improve its solubility, especially for salt formation. In this work, six colorful PRT salts, i.e., maleate, besylate, tosylate, phthalate, edisylate, and naphthalene disulfonate, were obtained for the first time and identified with solid-state characterization methods. The Hirshfeld surface and independent gradient model based on Hirshfeld partition calculation were used to study the weak interactions in crystal constitutions. With different counterions added into the unit cell and bonded with PRT cations through N+–H···O– hydrogen interactions, tremendous enhancement in water solubility and dissolution behavior was observed in all salts when compared with PRT. Solvation free energy and lattice energy were calculated to rationalize the increase in solubility values. Different colors exhibited in PRT salts were studied in detail with the molecular orbital caculation and visualization technique. The exploration in the landscape of PRT salt forms with increased water solubility and dissolution performance was highly promising for application in the drug-resistant tuberculosis treatment.

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The derivation and characterization of quinine charge-transfer complexes with inorganic and organic acceptors in liquid and solid form

Cited by 4 publications

References 126 publications

High-Quality Circularly Polarized Organic Afterglow from Nonconjugated Amorphous Chiral Copolymers

High-Quality Circularly Polarized Organic Afterglow from Nonconjugated Amorphous Chiral Copolymers

Synthesis and structure of new modified derivatives based on the quinine molecule and their biological activity

Colorful Prothionamide Salt Forms with Enhancement in Water Solubility and Dissolution Behavior

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