A5079278779- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Luminescence and Fluorescent Materials
- Molecular Sensors and Ion Detection
- Nanoplatforms for cancer theranostics
- Porphyrin and Phthalocyanine Chemistry
- Catalytic Cross-Coupling Reactions
- Catalytic C–H Functionalization Methods
- Chemical Synthesis and Analysis
- Asymmetric Hydrogenation and Catalysis
- Organic Light-Emitting Diodes Research
- Click Chemistry and Applications
- Synthetic Organic Chemistry Methods
- Organometallic Complex Synthesis and Catalysis
- Cyclopropane Reaction Mechanisms
- Organoboron and organosilicon chemistry
- Photochromic and Fluorescence Chemistry
- Sulfur-Based Synthesis Techniques
- Ferrocene Chemistry and Applications
- Polydiacetylene-based materials and applications
- Asymmetric Synthesis and Catalysis
- Bioactive Compounds and Antitumor Agents
- Synthesis and Reactivity of Heterocycles
- Chemical Synthesis and Reactions
- Chemical synthesis and alkaloids
Universidad de Guanajuato
2015-2024
Division of Chemistry
2019
University of the Basque Country
2013-2014
Instituto de Química Orgánica General
2014
Hong Kong University of Science and Technology
2009
University of Hong Kong
2009
West Virginia University
2008
Universidad Autónoma de Madrid
2007
Emory University
1995-2001
Benemérita Universidad Autónoma de Puebla
2000
Boron dipyrromethene (BODIPY) derivatives 1 and 2 consisting of donor acceptor units with dual photoresponses to solvent polarity luminogen aggregation are developed through taking advantage twisted intramolecular charge transfer (TICT) aggregation-induced emission (AIE) processes. In nonpolar solvents, the locally excited (LE) states BODIPY luminogens emit intense green lights. Increasing brings from LE state TICT state, causing a large bathochromic shift in color but dramatic decrease...
A series of tetraphenylethene-containing BODIPYs with emissions from visible to near-IR and large Stokes shifts up 142 nm have been designed synthesized. They show solvatochromic fluorescence can be utilized as fluorescent visualizers for intracellular imaging.
Fully unsubstituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) 1 was prepared. Reaction of 8-thiomethylbodipy 2 with triethylsilane in the presence a catalytic amount Pd and stoichiometric copper(I) thienyl-2-carboxylate (CuTC) THF at 55 degrees C gave compound nearly quantitative yield. This displays high quantum yields (up to 93%) polar solvents including water. Its optical properties crystal structure are discussed.
Abstract The development of highly efficient and stable blue‐emitting dyes to overcome some the most important shortcomings available chromophores is great technological importance for modern optical, analytical, electronic, biological applications. Here, we report design, synthesis characterization new tailor‐made BODIPY with absorption emission in blue spectral region. major challenge effective management electron‐donor strength substitution pattern, order modulate these novel over a wide...
Highly emitting 8-propargylaminoBODIPY (8-PAB) 2 was prepared in 94% yield. Unlike any other BODIPY structure hitherto described the literature, displays efficient emission blue region of visible spectrum with a fluorescence quantum yield up to 0.94 and high laser efficiency (35%) at 483 nm.
Abstract Fluorescence labelling of an intracellular biomolecule in native living cells is a powerful strategy to achieve in-depth understanding the biomolecule’s roles and functions. Besides being nontoxic specific, desirable probes should be highly cell permeable without nonspecific interactions with other cellular components warrant high signal-to-noise ratio. While it critical, rational design for such tricky. Here we report first predictive model background-free probe development through...
A series of BODIPY derivatives with tetraphenylethene (TPE) moieties were designed and synthesized. The effect positions numbers substitution groups on the fluorescence BODIPYs was investigated. Theoretical calculation single crystal structures proved that TPE 8-position contributed little to conjugation, but benefited aggregated state emission. On other hand, substitutions 3- or 5-position through vinyl bridges increased conjugation length, generated big coplanar π-conjugated poor compound...
A series of 14 meso-polyarylamine-BODIPY (borondipyrromethene) hybrids the general structure were synthesized. Two methods used to prepare them. The first protocol involved a direct Liebeskind−Srogl cross-coupling thiomethylbodipys 1−2 with arylaminoboronic acids (4 examples, 75−98%). second method involves two-step sequence: reaction 6 meso-bromoarylbodipys (58−83%) followed by Suzuki coupling these Br-containing BODIPYs (10 44−84%). Seven derivatives displayed emission in near-infrared...
An unprecedented synthesis of 8-substituted-borondipyrromethenes is described starting from 8-thiomethylbodipy 1. Aryl, heteroaryl, alkenyl, and organometallic boronic acids smoothly reacted with 1 in the presence a catalytic amount Pd(0) stoichiometric Cu(I)-2-thienylcarboxylate under neutral conditions to give corresponding Bodipy analogues good quantitative yields (20 examples). A remarkable reactivity was observed some cases, e.g., ferrocenylboronic acid gave product 98% isolated yield...
The role of the amino group twisting ability in BODIPY photophysics for nonsterically hindered and constrained molecular structures was studied. When a coplanar disposition core is feasible, hemicyanine-like delocalized π-system gives rise to novel blue efficient laser dyes. key such rotamer confirmed by newly synthesized derivatives where are electronically decoupled steric repulsions.
Most of the somatic embryogenesis (SE) process requires presence, either before or during embryogenic process, at least one exogenous auxin. This auxin induces presence endogenous auxins, which appears to be essential for SE induction. We found that preincubation period in Coffea canephora, there is an important increase both free and conjugated indole-3-acetic acid (IAA), as well indole-3-butyric acid. accompanied by expression YUCCA (CcYUC), TRYPTOPHAN AMINOTRANSFERASE OF ARABIDOPSIS 1...
Molecular mechanics calculations were used to probe the conformational properties of a number substituted phenanthrolines and their η3-allylpalladium complexes. Special attention was focused on bearing chiral, terpene-derived, alkyl alkenyl groups at C(2). Based upon these calculations, predictions could then be made regarding suitability several ligands for use in asymmetric palladium-catalyzed substitution reactions allylic acetates. Each prepared by straightforward means. Use catalytic...
Chemoselective cross-coupling reactions were demonstrated for C-S bonds in the BODIPY dyes 1 and 4, similar applied to make two-dye cassette system 11.
We report the photophysical properties of new BODIPY derivatives monosubstituted at central position. The presence different functional groups induced appearance processes in dyes, such as intramolecular charge or energy transfer. These phenomena are sensitive to solvent (mainly polarity) and have a potential use fluorescent probes. Adequate modifications their molecular structure environment polarity can modulate emission region these fluorophores visible spectral region. Specifically,...
Abstract A series of meso ‐substituted boron‐bipyrromethene (BODIPY) dyes are synthesized and their laser photophysical properties systematically studied. Laser emission covering a wide visible spectral region (from blue to orange) is obtained by just changing the electron donor character heteroatom at position 8. The additional presence methyl groups positions 3 5 results in with photostability similar that unsubstituted dye but much improved efficiency. Correlation lasing different...
Coumarin–BODIPY energy transfer laser dyes have been designed and tested as versatile, tunable photostable active media for UV irradiation.
We demonstrate herein that both alcohols and phenols can be tagged with a BODIPY (borondipyrromethene) moiety to yield highly fluorescent products. Thus, 8-(methylthio)-BODIPY (1) undergoes an S(N)Ar-type reaction host of in the presence base Cu(I) additive. The dyes bearing alkoxy or nonfunctionalized phenoxy moieties are characterized by efficient fluorescence emission, regardless media, blue-green part visible region. Complementary this, electron-donor groups at aryl ring leads...
New 8-NR2-BODIPYs, R2 = H(i)Pr (3a), H(i)Bu (3b), and Et2 (4), are reported. Restricted rotation about the C8-N bond in such molecules has been observed for first time (3a 3b) evaluated using VT NMR. The fluorophores 3a 3b blue emitters, efficiency of emission is closely related to polarity solvent, e.g., hexane > toluene DCM THF MeOH H2O, an effect also noted by variation alcohol solvents H(CH2)nOH, n 1-6. In mixed-solvent systems, addition 10-15% more polar solvent results transformation...
Abstract Herein, we report the synthesis of polyfunctional BODIPY building blocks suitable to be subjected several reaction sequences with complete chemoselectivity, thereby allowing preparation complex derivatives in a versatile and programmable manner. The reactions included Liebeskind–Srogl cross‐coupling (LSCC), nucleophilic aromatic substitution ( S N Ar), Suzuki, Sonogashira, Stille couplings, desulfitative reduction MeS group. This novel synthetic protocol is powerful route design...
Abstract A thorough study of the photophysical and laser properties 8‐aminoboron dipyrromethene dyes was undertaken to determine role amine substitution spatial disposition on dyes. It found that fluorescent response varied significantly. Although primary amines give rise highly products at blue edge visible region, secondary yield nonfluorescent analogues in polar media. The crystal structures two are reported described. Steric hindrance higher electron‐releasing ability favor formation a...
We took advantage of the chemoselective meso-functionalization 2,3,5,6-tetrabromo-8-methylthioBODIPY 6 to prepare a series 2,3,5,6-tetrabromo-8-arylBODIPY derivatives suitable for SNAr substitution reactions with phenols exclusively at positions 3 and 5. Pd(0)-catalyzed intramolecular arylation reaction ensued on remaining brominated 2 give new family benzofuran-fused BODIPY dyes. This method utilizes readily available starting materials allows preparation title compounds excellent...
Several new examples of meso-(het)arylBODIPY were prepared via the Liebeskind-Srogl (L-S) cross-coupling reaction Biellmann BODIPYs (1a,b) and aryl- heteroarylboronic acids in good to excellent yield. It was shown that this could be carried out under microwave heating shorten times and/or increase illustrated organostannanes also participate L-S give corresponding BODIPY analogues short with yields. We analyze role substituent at sensitive meso position photophysical signatures these...
Eleven formyl-containing BODIPY dyes were prepared by means of either the Liebeskind-Srogl cross-coupling reaction or Vilsmeier reaction. These used as components in Passerini to give highly substituted dyes. A joined spectroscopic and theoretical characterization synthesized compounds was conducted unravel impact structural rigidity/flexibility on photophysical signatures. tested fluorescent trackers for phagocytosis. Additionally, they proved be useful stain different blood cells with an...