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 A Convenient Synthesis of Diketopyrrolopyrrole Dyes

Molecules ◽  
2021 ◽  
Vol 26 (16) ◽  
pp. 4758
Author(s):  
Vitor A. S. Almodôvar ◽  
Augusto C. Tomé
Keyword(s):  
High Performance ◽  
Coupling Reaction ◽  
Quantum Yields ◽  
Reaction Conditions ◽  
Fluorescence Quantum Yields ◽  
Cross Coupling Reaction ◽  
Convenient Synthesis ◽  
Organic Optoelectronic ◽  
High Fluorescence ◽  
Stokes Shifts

Diketopyrrolo[3,4-c]pyrroles (DPP) are high-performance organic optoelectronic materials. They have applications in solar cells, fluorescent probes, bioimaging, photodynamic/photothermal therapy, and in many other areas. This article reports a convenient two-step synthesis of various DPP dyes from Pigment Red 254, an inexpensive commercial pigment. The synthesis includes a Suzuki–Miyaura cross-coupling reaction of a bis(4-chlorophenyl)DPP derivative with aryl and hetaryl boronic acids under mild reaction conditions. The new dyes show large Stokes shifts and high fluorescence quantum yields, important features for their potential use in technical and biological applications.

scholarly journals Rapid Sequentially Palladium Catalyzed Four-Component Synthesis of Novel Fluorescent Biaryl-Substituted Isoxazoles

Catalysts ◽  
2020 ◽  
Vol 10 (12) ◽  
pp. 1412
Author(s):  
Tobias Deden ◽  
Lars May ◽  
Guido J. Reiss ◽  
Thomas J. J. Müller
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Photophysical Properties ◽  
Quantum Yields ◽  
Catalyst Loading ◽  
One Pot ◽  
Functional Theory ◽  
Fluorescence Quantum Yields ◽  
Palladium Catalyzed ◽  
High Fluorescence

A series of novel 3- and 5-biaryl-substituted isoxazoles was prepared by a rapid microwave-assisted four-component three-step synthesis: concatenating Sonogashira coupling, cyclocondensation, and Suzuki coupling in a one-pot fashion. The Pd-catalyst was successfully employed in the sense of a sequentially catalyzed process, i.e., without the addition of further catalyst loading. Biaryl-substituted isoxazoles with donor–acceptor decoration possess remarkable photophysical properties, such as high fluorescence quantum yields in solution up to ΦF = 0.86 and large Stokes shifts up to 10,000 cm−1. The experimental absorption and emission characteristics can be reproduced and rationalized by computations on the DFT (density functional theory) and TDDFT (time-dependent density functional theory) level of theory.

Ferromagnetic Chain Based on Verdazyl-Nitroxide Diradical

2020 ◽  
Author(s):  
Evgeny Tretyakov ◽  
Svetlana Zhivetyeva ◽  
Pavel Petunin ◽  
Dmitry Gorbunov ◽  
Nina Gritsan ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Ferromagnetic Coupling ◽  
Nitronyl Nitroxide ◽  
Triplet Ground State ◽  
One Dimensional ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Ferromagnetic Chain ◽  
High Yields

<p>Verdazyl-nitroxide diradicals were synthesized using the palladium-catalyzed cross-coupling reaction of the corresponding iodoverdazyls with a nitronyl nitroxide-2-ide gold(I) complex with high yields (up to 82%). The synthesized diradicals were found to be highly thermally stable and have a singlet (D<i>E</i><sub>ST</sub> » -64 cm<sup>–1</sup>) or triplet ground state (D<i>E</i><sub>ST</sub> ³ 25 and 100 cm<sup>–1</sup>), depending on which canonical hydrocarbon diradical type they belong to. Upon crystallization, triplet diradicals form unique one-dimensional (1D) spin <i>S</i> = 1 chains of organic diradicals with intrachain ferromagnetic coupling of <i>J</i>′/<i>k</i><sub>B</sub> from 3 to 6 K.</p>

scholarly journals Fluorinated Iron(ii) clathrochelate units in metalorganic based copolymers: improved porosity, iodine uptake, and dye adsorption properties

RSC Advances ◽  
2021 ◽  
Vol 11 (25) ◽  
pp. 14986-14995
Author(s):  
Suchetha Shetty ◽  
Noorullah Baig ◽  
Atikur Hassan ◽  
Saleh Al-Mousawi ◽  
Neeladri Das ◽  
...  
Keyword(s):  
Dye Adsorption ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Building Blocks ◽  
Adsorption Properties ◽  
Iodine Uptake ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

We report the synthesis of metalorganic copolymers made from the palladium catalyzed Sonogashira cross-coupling reaction between various iron(ii) clathrochelate building blocks with diethynyl–triptycene and fluorene derivatives.

scholarly journals Mechanistic Aspects of the Palladium‐Catalyzed Suzuki‐Miyaura Cross‐Coupling Reaction

2021 ◽  
Author(s):  
Massimo C. D'Alterio ◽  
Èric Casals-Cruañas ◽  
Nikolaos V. Tzouras ◽  
Giovanni Talarico ◽  
Steven P Nolan ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Direct Cross-Coupling Reaction Between Indenes and Electron-Deficient Alkenes.

ChemInform ◽  
2010 ◽  
Vol 41 (43) ◽  
pp. no-no
Author(s):  
Yun-He Xu ◽  
Wee-Jian Wang ◽  
Zhen-Kang Wen ◽  
Joshua Jonathan Hartley ◽  
Teck-Peng Loh
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
Direct Cross ◽  
Palladium Catalyzed
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