Browse
Submit Data
Databases
API
Help

Dataset Information

10 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of C ₃-symmetric star-shaped molecules containing α-amino acids and dipeptides via Negishi coupling as a key step.

ABSTRACT: We demonstrate a new synthetic strategy toward star-shaped C ₃-symmetric molecules containing α-amino acid (AAA) derivatives and dipeptides. In this regard, trimerization and Negishi cross-coupling reactions are used as the key steps starting from readily available 4'-iodoacetophenone and L-serine. These C ₃-symmetric molecules containing AAA moieties are useful to design new ligands suitable for asymmetric synthesis and peptide dendrimers.

SUBMITTER: Kotha S

PROVIDER: S-EPMC6369998 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Synthesis and Photophysical Properties of C 3-Symmetric Star-Shaped Molecules Containing Heterocycles Such as Furan, Thiophene, and Oxazole.

Project description:We report simple strategies to synthesize star-shaped molecules containing different heterocycles integrated with a number of variations. Here, cyclotrimerization, Vilsmeier-Haack reaction, Suzuki-Miyaura cross-coupling, and Van Leusen oxazole synthesis have been used as key steps to introduce diverse five-membered heterocycles such as furan, thiophene, and oxazole. More importantly, readily available starting materials such as thiophene, 2-formyl furan, and 2-acetyl furan were utilized. Also, the fluorescent behavior of these π-conjugated systems was studied. C 3-Symmetric molecules containing furan moieties show a stronger fluorescence than thiophene-containing star-shaped compounds.

| S-EPMC6645079 | biostudies-literature

Conductance through single biphenyl molecules: symmetric and asymmetric coupling to electrodes.

Project description:The contacts and the chemical bonds formed between metallic electrodes and molecules determine to a large extent the conductive properties of single molecular junctions, which represent the smallest possible active elements in an electronic circuit. We therefore investigated in a comparative study, using the break junction technique (MCBJ), the conductive properties of [1,1'-biphenyl]-4,4'-dithiol (M1) and of 4'-mercapto-[1,1'-biphenyl]-4-carbonitrile (M2) between gold electrodes. As a function of electrode separation, characterized by the conductance close to 0 V, we found several plateaus of relative stability, with those close to 0.01G0 being the most pronounced. The overall conductance of symmetric and asymmetric molecules were surprisingly similar, only the range of stability was smaller for M2. While M1 yielded symmetric I-V-curves, only small asymmetries were detected for M2. These are also reflected in the comparable values for coupling parameters using the single level resonance model. The high conductance for the asymmetric molecule is interpreted as a result of coherent coupling of electronic states through the whole molecule, so that the outcome cannot be predicted just by adding conductive properties of individual molecular groups.

| S-EPMC4578413 | biostudies-literature

Step-saving synthesis of star-shaped hole-transporting materials with carbazole or phenothiazine cores via optimized C-H/C-Br coupling reactions.

Project description:In most research papers, synthesis of organic hole-transporting materials relies on a key-reaction: Stille cross-couplings. This requires tedious prefunctionalizations including the preparation and treatment of unstable organolithium and toxicity-concern organotin reagents. In contrast to traditional multistep synthesis, this work describes that a series of star-shaped small molecules with a carbazole or phenothiazine core can be efficiently synthesized through a shortcut using optimized direct C-H/C-Br cross-couplings as the key step, thus avoiding dealing with the highly reactive organolithium or the toxic organotin species. Device fabrication of perovskite solar cells employing these molecules (6-13) as hole-transporting layers exhibit promising power conversion efficiencies of up to 17.57%.

| S-EPMC8695233 | biostudies-literature

Star-Shaped Conjugated Systems

Project description:The present review deals with the preparation and the properties of star-shaped conjugated compounds. Three, four or six conjugated arms are attached to cross-conjugated cores, which consist of single atoms (B, C+, N), benzene or azine rings or polycyclic ring systems, as for example triphenylene or tristriazolotriazine. Many of these shape-persistent [n]star compounds tend to ?-stacking and self-organization, and exhibit interesting properties in materials science: Linear and non-linear optics, electrical conductivity, electroluminescence, formation of liquid crystalline phases, etc.

| S-EPMC5445917 | biostudies-literature

Synthesis of Benzofuropyridines and Dibenzofurans by a Metalation/Negishi Cross-Coupling/SNAr Reaction Sequence.

Project description:An efficient methodology for the synthesis of benzofuropyridines and dibenzofurans from fluoropyridines or fluoroarenes and 2-bromophenyl acetates is reported. This streamlined one-pot procedure consists of a four-step directed ortho-lithiation, zincation, Negishi cross-coupling, and intramolecular nucleophilic aromatic substitution, allowing for the facile assembly of a diverse set of fused benzofuro heterocycles.

| S-EPMC9830636 | biostudies-literature

Star-Shaped Magnetic-Plasmonic Au@Fe3O4 Nano-Heterostructures for Photothermal Therapy.

Project description:Here, we synthesize a Au@Fe3O4 core@shell system with a highly uniform unprecedented star-like shell morphology with combined plasmonic and magnetic properties. An advanced electron microscopy characterization allows assessing the multifaceted nature of the Au core and its role in the growth of the peculiar epitaxial star-like shell with excellent crystallinity and homogeneity. Magnetometry and magneto-optical spectroscopy revealed a pure magnetite shell, with a superior saturation magnetization compared to similar Au@Fe3O4 heterostructures reported in the literature, which is ascribed to the star-like morphology, as well as to the large thickness of the shell. Of note, Au@Fe3O4 nanostar-loaded cancer cells displayed magneto-mechanical stress under a low frequency external alternating magnetic field (few tens of Hz). On the other hand, such a uniform, homogeneous, and thick magnetite shell enables the shift of the plasmonic resonance of the Au core to 640 nm, which is the largest red shift achievable in Au@Fe3O4 homogeneous core@shell systems, prompting application in photothermal therapy and optical imaging in the first biologically transparent window. Preliminary experiments performing irradiation of a stable water suspension of the nanostar and Au@Fe3O4-loaded cancer cell culture suspension at 658 nm confirmed their optical response and their suitability for photothermal therapy. The outstanding features of the prepared system can be thus potentially exploited as a multifunctional platform for magnetic-plasmonic applications.

| S-EPMC9247976 | biostudies-literature

A periodic dodecagonal supertiling by self-assembly of star-shaped molecules in the liquid crystalline state.

Project description:Molecular tessellations are known in solid state systems and their formation is often induced or supported by a periodic surface lattice. Here we discover a complex tessellation on the 10 nm length scale, spontaneously formed in the highly dynamic liquid crystalline state. It is composed of overlapping dodecagonal supertiles combining prismatic cells with triangular and square cross sections. This complex honeycomb occurs between a triangular honeycomb at high and a square at low temperature, being opposite to the sequence expected for a thermal expansion of the side chains in the prismatic cells. Formation of the supertiles is supported by the segregation of alkyl chains with different length. The emergent behaviour of this complex soft matter structure is demonstrated, and intriguing connections between self-assembly on surfaces, in liquid crystals, and in block copolymers are drawn. Moreover, the tessellation represents a close approximant of the elusive columnar liquid quasicrystal with dodecagonal symmetry.

| S-EPMC9814142 | biostudies-literature

Synthesis of novel star-shaped molecules based on a 1,3,5-triazine core linked to different heterocyclic systems as novel hybrid molecules.

Project description:The synthesis of novel star-shaped compounds based on an s-triazine core and linked to hexahydroacridinediones, pyrimido[4,5-b]quinolones, 1H-isoquinolino[2,1-a]quinolines, tetrahydro-4H-chromenes, dihydropyrano[2,3-c]pyrazoles, thiazole, or benzothiazole as new hybrid molecules through Michael and Hantzsch reactions is reported. For this purpose, 2,4,6-tris(4-formylphenoxy)benzaldehyde was used as a versatile precursor.

| S-EPMC9058422 | biostudies-literature

Polypeptide Composition and Topology Affect Hydrogelation of Star-Shaped Poly(L-lysine)-Based Amphiphilic Copolypeptides.

Project description:In this research, we studied the effect of polypeptide composition and topology on the hydrogelation of star-shaped block copolypeptides based on hydrophilic, coil poly(L-lysine)20 (s-PLL20) tethered with a hydrophobic, sheet-like polypeptide segment, which is poly(L-phenylalanine) (PPhe), poly(L-leucine) (PLeu), poly(L-valine) (PVal) or poly(L-alanine) (PAla) with a degree of polymerization (DP) about 5. We found that the PPhe, PLeu, and PVal segments are good hydrogelators to promote hydrogelation. The hydrogelation and hydrogel mechanical properties depend on the arm number and hydrophobic polypeptide segment, which are dictated by the amphiphilic balance between polypeptide blocks and the hydrophobic interactions/hydrogen bonding exerted by the hydrophobic polypeptide segment. The star-shaped topology could facilitate their hydrogelation due to the branching chains serving as multiple interacting depots between hydrophobic polypeptide segments. The 6-armed diblock copolypeptides have better hydrogelation ability than 3-armed ones and s-PLL-b-PPhe exhibits better hydrogelation ability than s-PLL-b-PVal and s-PLL-b-PLeu due to the additional cation-π and π-π interactions. This study highlights that polypeptide composition and topology could be additional parameters to manipulate polypeptide hydrogelation.

| S-EPMC8482192 | biostudies-literature

Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers.

Project description:Mild transition-metal catalysed cross-couplings enable direct functionalisation of biocatalytically halogenated tryptophans with alkyl iodides, representing a new alternative for late-stage derivatisations of halogenated aromatic amino acids. Moreover, this strategy enables preparation of (homo)tryptophan regioisomers in a simple two-step synthesis using a Pd-catalysed Negishi cross coupling. This method provides access to non-canonical constitutional surrogates of tryptophan, ready for use in peptide synthesis.

| S-EPMC9299634 | biostudies-literature