scholarly journals Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization

2020 ◽  
Vol 16 ◽  
pp. 1683-1692 ◽  
Author(s):  
Dominik Göbel ◽  
Marius Friedrich ◽  
Enno Lork ◽  
Boris J Nachtsheim
Keyword(s):  
High Efficiency ◽  
Photophysical Properties ◽  
Covalent Attachment ◽  
Terminal Alkynes ◽  
Facile Synthesis ◽  
Triazole Derivatives ◽  
Emission Behavior ◽  
Substituted Benzaldehydes ◽  
Covalently Linked

Herein, we present a facile synthesis of three azide-functionalized fluorophores and their covalent attachment as triazoles in Huisgen-type cycloadditions with model alkynes. Besides two ortho- and para-bromo-substituted benzaldehydes, the azide functionalization of a fluorene-based structure will be presented. The copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) of the so-synthesized azide-functionalized bromocarbaldehydes with terminal alkynes, exhibiting different degrees of steric demand, was performed in high efficiency. Finally, we investigated the photophysical properties of the azide-functionalized arenes and their covalently linked triazole derivatives to gain deeper insight towards the effect of these covalent linkers on the emission behavior.

scholarly journals Fabrication of copper(II)-coated magnetic core-shell nanoparticles Fe3O4@SiO2-2-aminobenzohydrazide and investigation of its catalytic application in the synthesis of 1,2,3-triazole compounds

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
H. Rajabi-Moghaddam ◽  
M. R. Naimi-Jamal ◽  
M. Tajbakhsh
Keyword(s):  
High Efficiency ◽  
Click Reaction ◽  
Magnetic Core ◽  
Core Shell ◽  
Isatoic Anhydride ◽  
Shell Nanoparticles ◽  
Triazole Derivatives ◽  
Catalytic Application ◽  
Ft Ir ◽  
Core Shell Nanoparticles

AbstractIn the present work, an attempt has been made to synthesize the 1,2,3-triazole derivatives resulting from the click reaction, in a mild and green environment using the new copper(II)-coated magnetic core–shell nanoparticles Fe3O4@SiO2 modified by isatoic anhydride. The structure of the catalyst has been determined by XRD, FE-SEM, TGA, VSM, EDS, and FT-IR analyzes. The high efficiency and the ability to be recovered and reused for at least up to 6 consecutive runs are some superior properties of the catalyst.

scholarly journals Correction: Facile synthesis of ultrathin Ni-MOF nanobelts for high-efficiency determination of glucose in human serum

2020 ◽  
Vol 8 (25) ◽  
pp. 5547-5548
Author(s):  
Xiao Xiao ◽  
Shasha Zheng ◽  
Xinran Li ◽  
Guangxun Zhang ◽  
Xiaotian Guo ◽  
...  
Keyword(s):  
Human Serum ◽  
High Efficiency ◽  
Facile Synthesis ◽  
Efficiency Determination

Correction for ‘Facile synthesis of ultrathin Ni-MOF nanobelts for high-efficiency determination of glucose in human serum’ by Xiao Xiao et al., J. Mater. Chem. B, 2017, 5, 5234–5239, DOI: 10.1039/C7TB00180K.

scholarly journals Non-Covalent Binding of Tripeptides-Containing Tryptophan to Polynucleotides and Photochemical Deamination of Modified Tyrosine to Quinone Methide Leading to Covalent Attachment

Molecules ◽  
2021 ◽  
Vol 26 (14) ◽  
pp. 4315
Author(s):  
Antonija Erben ◽  
Igor Sviben ◽  
Branka Mihaljević ◽  
Ivo Piantanida ◽  
Nikola Basarić
Keyword(s):  
Quantum Yield ◽  
Photophysical Properties ◽  
Covalent Binding ◽  
Quinone Methide ◽  
Covalent Attachment ◽  
Dna And Rna ◽  
Pair Composition ◽  
Aqueous Solvent ◽  
Fluorometric Study ◽  
Spectral Responses

A series of tripeptides TrpTrpPhe (1), TrpTrpTyr (2), and TrpTrpTyr[CH2N(CH3)2] (3) were synthesized, and their photophysical properties and non-covalent binding to polynucleotides were investigated. Fluorescent Trp residues (quantum yield in aqueous solvent ΦF = 0.03–0.06), allowed for the fluorometric study of non-covalent binding to DNA and RNA. Moreover, high and similar affinities of 2×HCl and 3×HCl to all studied double stranded (ds)-polynucleotides were found (logKa = 6.0–6.8). However, the fluorescence spectral responses were strongly dependent on base pair composition: the GC-containing polynucleotides efficiently quenched Trp emission, at variance to AT- or AU-polynucleotides, which induced bisignate response. Namely, addition of AT(U) polynucleotides at excess over studied peptide induced the quenching (attributed to aggregation in the grooves of polynucleotides), whereas at excess of DNA/RNA over peptide the fluorescence increase of Trp was observed. The thermal denaturation and circular dichroism (CD) experiments supported peptides binding within the grooves of polynucleotides. The photogenerated quinone methide (QM) reacts with nucleophiles giving adducts, as demonstrated by the photomethanolysis (quantum yield ΦR = 0.11–0.13). Furthermore, we have demonstrated photoalkylation of AT oligonucleotides by QM, at variance to previous reports describing the highest reactivity of QMs with the GC reach regions of polynucleotides. Our investigations show a proof of principle that QM precursor can be imbedded into a peptide and used as a photochemical switch to enable alkylation of polynucleotides, enabling further applications in chemistry and biology.

scholarly journals Bis-NHC–Ag/Pd(OAc)2 Catalytic System Catalyzed Transfer Hydrogenation Reaction

Catalysts ◽  
2020 ◽  
Vol 11 (1) ◽  
pp. 8
Author(s):  
Hui-Ju Chen ◽  
Chien-Cheng Chiu ◽  
Tsui Wang ◽  
Dong-Sheng Lee ◽  
Ta-Jung Lu
Keyword(s):  
Functional Groups ◽  
Catalytic System ◽  
High Efficiency ◽  
Aqueous Media ◽  
Hydrogenation Reaction ◽  
Transfer Hydrogenation ◽  
Terminal Alkynes ◽  
Wide Range ◽  
Transfer Hydrogenation Reaction

The bis-NHC–Ag/Pd(OAc)2 catalytic system (NHC = N-heterocyclic carbene), a combination of bis-NHC–Ag complex and Pd(OAc)2, was found to be a smart catalyst in the Pd-catalyzed transfer hydrogenation of various functionalized arenes and internal/terminal alkynes. The catalytic system demonstrated high efficiency for the reduction of a wide range of various functional groups such as carbonyls, alkynes, olefins, and nitro groups in good to excellent yields and high chemoselectivity for the reduction of functional groups. In addition, the protocol was successfully exploited to stereoselectivity for the transformation of alkynes to alkenes in aqueous media under air. This methodology successfully provided an alternative useful protocol for reducing various functional groups and a simple operational protocol for transfer hydrogenation.

scholarly journals Organic Nanoparticles Based on D-A-D Small Molecule: Self-Assembly, Photophysical Properties, and Synergistic Photodynamic/Photothermal Effects

Materials ◽  
2022 ◽  
Vol 15 (2) ◽  
pp. 502
Author(s):  
Liangliang Yue ◽  
Haolan Li ◽  
Qi Sun ◽  
Xiaogang Luo ◽  
Fengshou Wu ◽  
...  
Keyword(s):  
Self Assembly ◽  
Organic Molecule ◽  
High Efficiency ◽  
Photophysical Properties ◽  
Coupling Reaction ◽  
Ros Generation ◽  
Dead Cell ◽  
Minimal Invasiveness ◽  
Sonogashira Coupling Reaction ◽  
Potential Strategy

Cancer is one of the major diseases threatening human health. Traditional cancer treatments have notable side-effects as they can damage the immune system. Recently, phototherapy, as a potential strategy for clinical cancer therapy, has received wide attention due to its minimal invasiveness and high efficiency. Herein, a small organic molecule (PTA) with a D-A-D structure was prepared via a Sonogashira coupling reaction between the electron-withdrawing dibromo-perylenediimide and electron-donating 4-ethynyl-N,N-diphenylaniline. The amphiphilic organic molecule was then transformed into nanoparticles (PTA-NPs) through the self-assembling method. Upon laser irradiation at 635 nm, PTA-NPs displayed a high photothermal conversion efficiency (PCE = 43%) together with efficient reactive oxygen species (ROS) generation. The fluorescence images also indicated the production of ROS in cancer cells with PTA-NPs. In addition, the biocompatibility and photocytotoxicity of PTA-NPs were evaluated by 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and live/dead cell co-staining test. Therefore, the as-prepared organic nanomaterials were demonstrated as promising nanomaterials for cancer phototherapy in the clinic.

scholarly journals Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines

Molecules ◽  
2019 ◽  
Vol 24 (13) ◽  
pp. 2386 ◽  
Author(s):  
Natalia A. Danilkina ◽  
Nina S. Bukhtiiarova ◽  
Anastasia I. Govdi ◽  
Anna A. Vasileva ◽  
Andrey M. Rumyantsev ◽  
...  
Keyword(s):  
Photoinduced Electron Transfer ◽  
Functional Group ◽  
Click Reaction ◽  
Bromine Atom ◽  
Photophysical Properties ◽  
Triazole Ring ◽  
Synthetic Approach ◽  
Terminal Alkynes ◽  
Reaction Products ◽  
Fluorescent Properties

An efficient approach towards the synthesis of 6-aryl-4-azidocinnolines was developed with the aim of exploring the photophysical properties of 6-aryl-4-azidocinnolines and their click reaction products with alkynes, 6-aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines. The synthetic route is based on the Richter-type cyclization of 2-ethynyl-4-aryltriazenes with the formation of 4-bromo-6-arylcinnolines and nucleophilic substitution of a bromine atom with an azide functional group. The developed synthetic approach is tolerant to variations of functional groups on the aryl moiety. The resulting azidocinnolines were found to be reactive in both CuAAC with terminal alkynes and SPAAC with diazacyclononyne, yielding 4-triazolylcinnolines. It was found that 4-azido-6-arylcinnolines possess weak fluorescent properties, while conversion of the azido function into a triazole ring led to complete fluorescence quenching. The lack of fluorescence in triazoles could be explained by the non-planar structure of triazolylcinnolines and a possible photoinduced electron transfer (PET) mechanism. Among the series of 4-triazolylcinnoline derivatives a compound bearing hydroxyalkyl substituent at triazole ring was found to be cytotoxic to HeLa cells.

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