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.

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).

Red-emitting boron difluoride complexes with a mega-large Stokes shift and unexpectedly high fluorescence quantum yield

2020 ◽  
Vol 56 (14) ◽  
pp. 2159-2162 ◽  
Author(s):  
Xiaojie Ren ◽  
Fan Zhang ◽  
Hongchen Luo ◽  
Lide Liao ◽  
Xiangzhi Song ◽  
...  
Keyword(s):  
Quantum Yield ◽  
Fluorescence Quantum Yield ◽  
Stokes Shift ◽  
Quantum Yields ◽  
Large Stokes Shift ◽  
Fluorescence Quantum Yields ◽  
Boron Difluoride ◽  
High Fluorescence ◽  
Stokes Shifts ◽  
High Fluorescence Quantum Yield

Introduction of a tetrahydroquinoxaline donor into boron difluoride complexes largely extended their emissions (617–684 nm), highly improved their fluorescence quantum yields (up to 0.68) and greatly increased their Stokes shifts (up to 209 nm).

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
Author(s):  
Jorge A. Cabezas ◽  
Natasha Ferllini
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkyne ◽  
Copper Iodide ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

Chlorination vs. fluorination: a study of halogenated benzo[c][1,2,5]thiadiazole-based organic semiconducting dots for near-infrared cellular imaging

2020 ◽  
Vol 44 (19) ◽  
pp. 7740-7748
Author(s):  
Daize Mo ◽  
Li Lin ◽  
Pengjie Chao ◽  
Hanjian Lai ◽  
Qingwen Zhang ◽  
...  
Keyword(s):  
Near Infrared ◽  
Cellular Imaging ◽  
Quantum Yields ◽  
Fluorescence Quantum Yields ◽  
Stokes Shifts

The chlorinated dots based on chlorinated benzo[c][1,2,5]thiadiazole unit possess higher fluorescence quantum yields, larger Stokes shifts, and better photostability than the fluorinated dots.

scholarly journals Photoluminescence in m-carborane–anthracene triads: a combined experimental and computational study

2018 ◽  
Vol 6 (42) ◽  
pp. 11336-11347 ◽  
Author(s):  
Mahdi Chaari ◽  
Zsolt Kelemen ◽  
José Giner Planas ◽  
Francesc Teixidor ◽  
Duane Choquesillo-Lazarte ◽  
...  
Keyword(s):  
Computational Study ◽  
Fluorescence Emission ◽  
Fluorescence Properties ◽  
Quantum Yields ◽  
Aggregate State ◽  
Fluorescence Quantum Yields ◽  
High Fluorescence

m-Carborane has demonstrated to be a perfect platform to boost the fluorescence properties of anthracene, giving rise to high fluorescence quantum yields in solution and also retaining fluorescence emission in the aggregate state.

Synthesis and Photophysical Properties of 3-(Trifluoromethyl)-2H-imidazo[5,1-a]isoquinolinium Chloride Derivatives

Synlett ◽  
2017 ◽  
Vol 29 (03) ◽  
pp. 296-300 ◽  
Author(s):  
Ali Darehkordi ◽  
Fariba Rahmani ◽  
Mahin Ramezani ◽  
Alireza Bazmandegan-Shamili
Keyword(s):  
Blue Light ◽  
Uv Radiation ◽  
Photophysical Properties ◽  
Molecular Probes ◽  
Quantum Yields ◽  
Light Emitting ◽  
Fluorescence Studies ◽  
Fluorescence Quantum Yields ◽  
Fluorescent Molecular Probes ◽  
Stokes Shifts

A series of novel blue-light-emitting 2H-imidazo[5,1-a]isoquinolinium chloride derivatives were synthesized by the reaction of isoquinoline with trifluoroacetimidoyl chlorides and isocyanides in dry CH2Cl2 in excellent yields. Fluorescence studies showed that the compounds absorb UV radiation and then emit blue light at about 481 nm with moderate to good fluorescence quantum yields. These compounds also showed high Stokes shifts, and can be used to develop ­ultrasensitive fluorescent molecular probes to study a variety of biological events and processes.

scholarly journals Thiophene-forming one-pot synthesis of three thienyl-bridged oligophenothiazines and their electronic properties

2016 ◽  
Vol 12 ◽  
pp. 2055-2064 ◽  
Author(s):  
Dominik Urselmann ◽  
Konstantin Deilhof ◽  
Bernhard Mayer ◽  
Thomas J J Müller
Keyword(s):  
Cyclic Voltammetry ◽  
Helical Structure ◽  
Quantum Yields ◽  
Absorption Bands ◽  
One Pot ◽  
Fluorescence Quantum Yields ◽  
Oxidation Potentials ◽  
Td Dft ◽  
Lower Oxidation ◽  
Stokes Shifts

The pseudo five-component Sonogashira–Glaser cyclization synthesis of symmetrically 2,5-diaryl-substituted thiophenes is excellently suited to access thienyl-bridged oligophenothiazines in a one-pot fashion. Three thienyl-bridged systems were intensively studied by UV–vis and fluorescence spectroscopy as well as by cyclic voltammetry. The oxidation proceeds with lower oxidation potentials and consistently reversible oxidations can be identified. The Stokes shifts are large and substantial fluorescence quantum yields can be measured. Computational chemistry indicates lowest energy conformers with sigmoidal and helical structure, similar to oligophenothiazines. TD-DFT and even semiempirical ZINDO calculations reproduce the trends of longest wavelengths absorption bands and allow the assignment of these transitions to possess largely charge-transfer character from the adjacent phenothiazinyl moieties to the central thienyl unit.

Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: Tetraorganosilanes for the practical cross-coupling reaction

2006 ◽  
Vol 78 (2) ◽  
pp. 435-440 ◽  
Author(s):  
Yoshiaki Nakao ◽  
Akhila K. Sahoo ◽  
Hidekazu Imanaka ◽  
Akira Yada ◽  
Tamejiro Hiyama
Keyword(s):  
Functional Groups ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Hydroxyl Group ◽  
Axial Position ◽  
Silyl Ether ◽  
Intramolecular Coordination ◽  
Reaction Conditions ◽  
Diverse Range ◽  
Cross Coupling Reaction

Readily accessible and highly stable alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes cross-couple with various aryl and alkenyl halides under mild reaction conditions employing K2CO3 as a base at 35-80 °C. The reaction tolerates a diverse range of functional groups including silyl protections. The silicon residue, cyclic silyl ether, is readily recovered and reused on a gram-scale synthesis. Intramolecular coordination of a proximal hydroxyl group is considered to efficiently form pentacoordinated silicates having a transferable group at an axial position.

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