Biologically-Active Heterocyclic Molecules with Aggregation-Induced Blue-Shifted Emission and Efficient Luminescence both in Solution and Solid States

Younis, Osama; Tolba, Mahmoud S.; Orabi, Esam A.; Kamal, Ahmed A. M.; Hassanien, Reda; Tsutsumi, Osamu; Ahmed, Mostafa

doi:10.1016/j.jphotochem.2020.112642

Cited by 19 publications

(14 citation statements)

References 59 publications

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“…On the other hand, a concentrated solution of compound 5 (1×10 −5 mol L −1 ) exhibited a blue shift compared to its dilute solution (1×10 −7 mol L −1 , λ max =382 nm). This unusual behavior has already been reported [9,57] …”

Section: Resultssupporting

confidence: 78%

“…This unusual behavior has already been reported. [9,57] The blue shift is the exact reverse of the normal pattern in classic fluorescent substances, where aggregation promotes a red shift. The conjugated effect appears to be weakened by a specific mechanism when the compound 5 molecules aggregate, resulting in a blue shift in the emission wavelength.…”

Section: And Maximum Amount Of Electronic Charge (mentioning

confidence: 98%

“…[3,5] We have also reported some pyrimidine derivatives having both biological activities and luminescence efficiency. [8,9] Coumarin is also regarded as a wealthy heterocyclic scaffold for medicinal chemistry, and it is widely used in the development of new biologically active compounds. [10] Moreover, the coumarin nucleus has been widely used in the design of photo-and electroactive materials, [11,12] including fluorescent chemosensors, [13] laser dyes, [14] and light-harvesting dyes for dye-sensitized solar cells.…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, various pyrimidine analogs have been discovered to have antibacterial, [2,3] antifungal, [4,5] anticancer agents, [6–8] anti‐inflammatory [3,5] . We have also reported some pyrimidine derivatives having both biological activities and luminescence efficiency [8,9] . Coumarin is also regarded as a wealthy heterocyclic scaffold for medicinal chemistry, and it is widely used in the development of new biologically active compounds [10] .…”

Section: Introductionmentioning

confidence: 99%

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From Blue to Green Photoluminescence: Design, Synthesis, and DFT Calculations of Heterocyclic Compounds Containing Chromenothienopyrimidine Moiety

et al. 2022

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Incorporating coumarin nuclei into other heterocyclic scaffolds such as thienopyrimidine can significantly increase the photophysical and biological efficiency. Accordingly, we describe in this manuscript the synthesis of new heterocyclic derivatives containing combined coumarin and pyrimidine nuclei to maximize the application benefit of the target compounds. All of the synthesized derivatives were thoroughly characterized using spectral analyses such as FT-IR, NMR, and mass spectroscopy. The photophysical proper-ties of four compounds in solution were investigated, where the substitutions had a significant effect even when the molecule conjugation was not included. Although having similar luminescent cores, two analog compounds showed different emission colors, blue and green. Uncommonly, one derivative showed a blue shift after aggregation. DFT simulations showed that adding a terminal group can significantly alter the electronic structure or molecular packing which affected directly the luminescence behavior.

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Section: Resultssupporting

confidence: 78%

Section: And Maximum Amount Of Electronic Charge (mentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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From Blue to Green Photoluminescence: Design, Synthesis, and DFT Calculations of Heterocyclic Compounds Containing Chromenothienopyrimidine Moiety

et al. 2022

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“… 24 − 29 Some indole derivatives and other heterocyclic compounds have been designed and showed aggregation-induced emission properties. 22 , 30 − 32 Thus, Schiff bases with indole moieties may have some interesting optical properties. However, limited studies have exclusively examined such materials.…”

Section: Introductionmentioning

confidence: 99%

Base-Free Synthesis and Photophysical Properties of New Schiff Bases Containing Indole Moiety

et al. 2022

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Schiff bases represent an essential class in organic chemistry with antitumor, antiviral, antifungal, and antibacterial activities. The synthesis of Schiff bases requires the presence of an organic base as a catalyst such as piperidine. Base-free synthesis of organic compounds using a heterogeneous catalyst has recently attracted more interest due to the facile procedure, high yield, and reusability of the used catalyst. Herein, we present a comparative study to synthesize new Schiff bases containing indole moieties using piperidine as an organic base catalyst and Au@TiO 2 as a heterogeneous catalyst. In both methods, the products were isolated in high yields and fully characterized using different spectral analysis techniques. The catalyst was reusable four times, and the activity was slightly decreased. The presence of Au increases the number of acidic sites of TiO 2 , resulting in C=O polarization. Yields of the prepared Schiff bases in the presence of Au@TiO 2 and piperidine were comparable. However, Au@TiO 2 is an easily separable and recyclable catalyst, which would facilitate the synthesis of organic compounds without applying any hazardous materials. Furthermore, the luminescence behavior of the synthesized Schiff bases exhibited spectral shape dependence on the substituent group. Interestingly, the compounds also displayed deep-blue fluorescence with Commission Internationale de l’Éclairage (CIE) coordinates of y < 0.1. Thus, these materials may contribute to decreasing the energy consumption of the emitting devices.

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Recent trends in molecular aggregates: An exploration of biomedicine

et al. 2022

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Molecular aggregates are receiving tremendous attention, demonstrating immense potential for biomedical applications in vitro and in vivo. For instance, the molecular aggregates of conventional fluorophores influence the electronic excitation states of the aggregates, causing characteristic photophysical property changes. A fundamental understanding of this classical relationship between molecular aggregate structures and photophysics has allowed for innovative biological applications. The chemical characteristics of drug molecules generally trigger the formation of colloidal aggregates, and this is considered detrimental to the drug discovery process. Furthermore, nano-sized supramolecular aggregates have been used in biomedical imaging and therapy owing to their optimal properties for in vivo utility, including enhanced cell permeability, passive tumor targeting, and convenient surface engineering. Herein, we provide an overview of the recent trends in molecular aggregates for biomedical applications. The changes in photophysical properties of conventional fluorophores and their biological applications are discussed, followed by the effects of conventional drug molecule-aggregates on drug discovery and therapeutics development. Recent trends in the investigation of biologically important analytes with aggregation-induced emission are discussed for conventional and unconventional fluorophores. Lastly, we discuss nano-sized supramolecular aggregates used in imaging and therapeutic purposes, with a focus on in vivo utilization.

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Biologically-Active Heterocyclic Molecules with Aggregation-Induced Blue-Shifted Emission and Efficient Luminescence both in Solution and Solid States

Cited by 19 publications

References 59 publications

From Blue to Green Photoluminescence: Design, Synthesis, and DFT Calculations of Heterocyclic Compounds Containing Chromenothienopyrimidine Moiety

From Blue to Green Photoluminescence: Design, Synthesis, and DFT Calculations of Heterocyclic Compounds Containing Chromenothienopyrimidine Moiety

Base-Free Synthesis and Photophysical Properties of New Schiff Bases Containing Indole Moiety

Recent trends in molecular aggregates: An exploration of biomedicine

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