scholarly journals Design, Synthesis, and Photophysical Properties of BODIPY-Labeled Lupane Triterpenoids

2020 ◽  
Vol 3 (1) ◽  
pp. 11
Author(s):  
Rinat Gubaidullin ◽  
Darya Nedopekina ◽  
Adis Tukhbatullin ◽  
Eldar Davletshin ◽  
Anna Spivak
Keyword(s):  
Fluorescent Dyes ◽  
Photophysical Properties ◽  
Coupling Reaction ◽  
Sonogashira Reaction ◽  
Design Synthesis ◽  
Fluorescent Marker ◽  
Biological Assays ◽  
Lupane Triterpenoids ◽  
Cross Coupling Reaction ◽  
Coupling Procedure

Novel boron-dipyrromethene difluoride (4,4-difluoro-4-bora-3α,4α-diaza-s-indacene) (BODIPY)-lupane triterpenoid conjugates bearing a fluorescent marker at the C-2 position of ring A of the triterpene core were obtained via the Sonogashira reaction as a key step. The starting compounds in the cross-coupling reaction were C-2 propynyl derivatives of betulinic or betulonic acids and fluorescent dyes with an iodo-group at C-2 or meso position of BODIPY-platform. The newly elaborated coupling procedure might have applicability in the synthesis of fluorescently-labeled triterpenoid conjugates suitable for biological assays.

Synthesis and photophysical properties of pyrene-based green fluorescent dyes: butterfly-shaped architectures

2014 ◽  
Vol 12 (40) ◽  
pp. 7914-7918 ◽  
Author(s):  
Devendar Goud Vanga ◽  
Mithun Santra ◽  
Ashok Keerthi ◽  
Suresh Valiyaveettil
Keyword(s):  
Fluorescent Dyes ◽  
Photophysical Properties ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
Green Fluorescent ◽  
Fluorescent Compounds

A few pyrene-based fluorescent compounds were synthesized using Pd/Cu-catalyzed cross-coupling reaction.

Regioselective Oxidative Cross-Coupling Reaction: Synthesis of Imidazo[1,2-a]pyridine Fluorophores

Synthesis ◽  
2021 ◽  
Author(s):  
Xianglong Chu ◽  
Yadi Niu ◽  
Chen Ma ◽  
Xiaodong Wang ◽  
Yunliang Lin ◽  
...  
Keyword(s):  
Photophysical Properties ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Quantum Yields ◽  
Fluorescence Quantum Yields ◽  
Cross Coupling Reaction ◽  
Color Tunable ◽  
Palladium Catalyzed ◽  
Structure Relationship ◽  
High Fluorescence

AbstractA rapid access to a series of N-heteroarene fluorophores has been developed on the basis of the palladium-catalyzed direct oxidative C–H/C–H coupling of imidazo[1,2-a]pyridines with thiophenes/furans. The photophysical properties–structure relationship was systematically investigated. The resulting N-heteroarene fluorophores present color-tunable emissions (λem: 431–507 nm in CH2Cl2) and high fluorescence quantum yields (up to 91% in CH2Cl2).

scholarly journals Highly Luminescent 4H-1,2,4-Triazole Derivatives: Synthesis, Molecular Structure and Photophysical Properties

Materials ◽  
2020 ◽  
Vol 13 (24) ◽  
pp. 5627
Author(s):  
Monika Olesiejuk ◽  
Agnieszka Kudelko ◽  
Marcin Świątkowski
Keyword(s):  
Photophysical Properties ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Luminescent Properties ◽  
Boronic Acids ◽  
Molecular Structures ◽  
X Ray ◽  
Cross Coupling Reaction ◽  
Alternative Approach ◽  
Large Quantum

An alternative approach to the Suzuki cross-coupling reaction is used to synthesize a series of new luminophores based on 4-alkyl-4H-1,2,4-triazole cores conjugated via 1,4-phenylene linker to fused-bicyclic and tricyclic aromatic, or heteroaromatic arrangements. The described methodology allows one to conduct the coupling reaction with the use of commercially available boronic acids in the presence of conventional solvents or ionic liquids and produced excellent yields. It was found that the use of ultrasounds or microwaves significantly accelerates the reaction. The obtained compounds exhibited high luminescent properties and a large quantum yield of emitted photons. The X-ray molecular structures of three highly conjugated 4H-1,2,4-triazole representatives are also presented.

Dynamic Pdᴵᴵ/Cuᴵ Multimetallic Assemblies as Molecular Models to Study Metal-Metal Cooperation in Sonogashira Coupling

2019 ◽  
Author(s):  
Orestes Rivada-Wheelaghan ◽  
Aleix Comas Vives ◽  
Robert Fayzullin ◽  
Agustí Lledós ◽  
Julia Khusnutdinova
Keyword(s):  
Coupling Reaction ◽  
Active Species ◽  
Sonogashira Reaction ◽  
Sonogashira Coupling ◽  
Dft Studies ◽  
Cross Coupling Reaction ◽  
Functional Models ◽  
Metal Metal ◽  
Cu Complexes ◽  
Current Systems

Cooperation between two different metals plays a crucial role in many synergistic catalytic reactions such as the Sonogashira C-C cross-coupling reaction, where an interaction between the organometallic Pd and Cu centers is proposed in the transmetalation step. Although several heterobimetallic Pd/Cu complexes were proposed as structural models of the active species in Sonogashira coupling, the detailed understanding of the metal-metal cooperation in both transmetalation and C-C elimination steps is still lacking in current systems. In this work, we report a stepwise and systematic approach to building heteromultimetallic Pd/Cu assemblies as a tool to study metal-metal cooperativity in catalysis. We obtained fully characterized Pd/Cu multimetallic assemblies that show reactivity in alkyne activation, formation of catalytically relevant aryl/acetylide species, and C-C elimination, serving as functional models for Sonogashira reaction intermediates. The combined experimental and DFT studies highlight the importance of ligand-controlled coordination geometry, metal-metal distances and dynamics of the multimetallic assembly for transmetalation step. The phosphine ligand was shown to promote facile C-C elimination explained through NMR and DFT studies.<br>

scholarly journals The CuFe2O4@SiO2@ZrO2/SO42−/Cu nanoparticles: an efficient magnetically recyclable multifunctional Lewis/Brønsted acid nanocatalyst for the ligand- and Pd-free Sonogashira cross-coupling reaction in water

RSC Advances ◽  
2019 ◽  
Vol 9 (36) ◽  
pp. 20749-20759 ◽  
Author(s):  
Mohammad Ali Nasseri ◽  
Seyyedeh Ameneh Alavi ◽  
Milad Kazemnejadi ◽  
Ali Allahresani
Keyword(s):  
Zirconium Oxide ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Reaction ◽  
Bronsted Acid ◽  
Cu Nanoparticles ◽  
Green Protocol ◽  
Cross Coupling Reaction ◽  
Brönsted Acid ◽  
Reaction In Water

A mild and green protocol was developed by immobilizing copper-incorporated sulfated zirconium oxide on CuFe2O4 as an efficient inorgano-nanocatalyst for the Sonogashira reaction.

scholarly journals Carbazole- and Triphenylamine-Substituted Pyrimidines: Synthesis and Photophysical Properties

Molecules ◽  
2019 ◽  
Vol 24 (9) ◽  
pp. 1742 ◽  
Author(s):  
Sylvain Achelle ◽  
Julián Rodríguez-López ◽  
Massinissa Larbani ◽  
Rodrigo Plaza-Pedroche ◽  
Françoise Robin-le Guen
Keyword(s):  
Solid State ◽  
Blue Light ◽  
Photophysical Properties ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Pyrimidine Derivatives ◽  
Absorption Bands ◽  
Cross Coupling Reaction

A series of pyrimidine derivatives bearing one, two or three triphenylamine/9-ethylcarbazole substituents has been synthesized by Suzuki cross-coupling reaction. All compounds showed absorption bands in the UV region and the emission of violet-blue light upon irradiation. Protonation led to quenching of the fluorescence, although some derivatives remained luminescent with the appearance of a new red-shifted band in the spectra. Accurate control of the amount of acid enabled white photoluminescence to be obtained both in solution and in solid state.

Design, synthesis, and anticancer activity of novel aryl/heteroaryl chalcone derivatives

2016 ◽  
Vol 22 (1) ◽  
pp. 1-5 ◽  
Author(s):  
Ananda Mohan Arasavelli ◽  
Ganapavarapu Veera Raghava Sharma ◽  
Siddaiah Vidavalur
Keyword(s):  
Anticancer Activity ◽  
Coupling Reaction ◽  
Human Colon ◽  
Human Colon Cancer Cell ◽  
Human Colon Cancer ◽  
Design Synthesis ◽  
Reference Drug ◽  
Cross Coupling Reaction ◽  
Colon Cancer Cell Lines

AbstractA new series of chalcones 5a–l were synthesized and evaluated for in vitro antiproliferative activity against human colon cancer cell lines. The synthesis of the key intermediate compounds 3a–d was achieved by tetrakis(triphenylphosphine) palladium(II) mediated Suzuki cross coupling reaction. Chalcone 5a shows superior anticancer activity with IC50 value of 21.0 μg/mL compared to the IC50 value of the reference drug doxorubicin at 21.65 μg/mL.

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