170159-16-7Relevant academic research and scientific papers
Carbazole-Based Tetrapodal Anchor Groups for Gold Surfaces: Synthesis and Conductance Properties
O'Driscoll, Luke J.,Wang, Xintai,Jay, Michael,Batsanov, Andrei S.,Sadeghi, Hatef,Lambert, Colin J.,Robinson, Benjamin J.,Bryce, Martin R.
, p. 882 - 889 (2020)
As the field of molecular-scale electronics matures and the prospect of devices incorporating molecular wires becomes more feasible, it is necessary to progress from the simple anchor groups used in fundamental conductance studies to more elaborate anchor
Reaction pathway change on plasmonic Au nanoparticles studied by surface-enhanced Raman spectroscopy
Li, Ran,Zhang, Can-Can,Wang, Dan,Hu, Yan-Fang,Li, Yong-Long,Xie, Wei
, p. 2846 - 2850 (2021)
Gold nanoparticles (Au NPs) are nanoscale sources of light and electrons, which are highly relevant for their extensive applications in the field of photocatalysis. Although a number of research works have been carried out on chemical reactions accelerated by the energetic hot electrons/holes, the possibility of reaction pathway change on the plasmonic Au surfaces has not been reported so far. In this proof-of-concept study, we find that Au NPs change the reaction pathway in photooxidation of alkyne under visible light irradiation. This reaction produces benzil ([sbnd]CO[sbnd]CO[sbnd]) without the presence of Au NPs. In contrast, as indicated by surface-enhanced Raman spectroscopic (SERS) results, the C[sbnd]C triple bonds ([sbnd]C[tbnd]C[sbnd]) adsorbed on Au NPs are converted into carboxyl ([sbnd]COOH) and acyl chloride ([sbnd]COCl) groups. The plasmonic Au NPs not only provide energetic charge carriers but also activate the reactant molecules as conventional heterogeneous catalysts. This study discloses the second role of plasmonic NPs in photocatalysis and bridges the gap between plasmon-driven and conventional heterogeneous catalysis.
Formation of high-quality self-assembled monolayers of conjugated dithiols on gold: Base matters
Valkenier, Hennie,Huisman, Everardus H.,Van Hal, Paul A.,De Leeuw, Dago M.,Chiechi, Ryan C.,Hummelen, Jan C.
, p. 4930 - 4939 (2011/06/23)
This Article reports a systematic study on the formation of self-assembled monolayers (SAMs) of conjugated molecules for molecular electronic (ME) devices. We monitored the deprotection reaction of acetyl protected dithiols of oligophenylene ethynylenes (
Rapid Solution and Solid Phase Syntheses of Oligo(1,4-phenylene ethynylene)s with Thioester Termini: Molecular Scale Wires with Alligator Clips. Derivation of Iterative Reaction Efficiencies on a Polymer Support
Jones II, LeRoy,Schumm, Jeffry S.,Tour, James M.
, p. 1388 - 1410 (2007/10/03)
The syntheses of soluble oligo(2-alkyl-l,4-phenylene ethynylene)s via an iterative divergent/ convergent approach starting from 1-(diethyltriazyl)-3-alkyl-4-[(trimethylsilyl)ethynyl]benzenes are described. When the solublizing alkyl group is an ethyl substituent, the monomer, dimer, tetramer, and octamer can be synthesized. The octamer, however, is only minimally soluble. When the alkyl substituent is 3-ethylheptyl or dodecyl, the compounds are easily dissolved even at the 16-mer stage. The 16-mer is 128 A long in its near-linear extended conformation. At each stage in the iteration, the length of the framework doubles. Only three sets of reaction conditions are needed for the entire iterative synthetic sequence: an iodination, a protodesilylation, and a Pd/Cu-catalyzed cross coupling. Synthesis of the dodecyl-containing 16-mer was also achieved on Merrifield's resin using the iterative divergent/convergent approach. The oligomers were characterized spectroscopically and by mass spectrometry. The optical properties are presented which show that at the octamer stage, the optical absorbance maximum is nearly saturated. The size exclusion chromatography values for the number average weights, relative to polystyrene, illustrate the tremendous differences in the hydrodynamic volume of these rigid rod oligomers verses the random coils of polystyrene. These differences become quite apparent at the octamer stage. Equations were derived for assessing the efficiency of the polymer-supported reactions based on resin weight differences, molar concentration differences, and elemental analysis data. Each of these methods' limitations are discussed. Attachment of thiol end groups, protected as thioacetyl moieties, was achieved. These serve as binding sites for adhesion to gold surfaces. In some cases, one end of the oligomeric chains is capped with a thiol group so that the surface attachments to gold could be studied. In other cases, thiol groups are affixed to both ends of the molecular chains so that future conduction studies could be done between proximal metallic probes. The rigid rod conjugated oligomers may act as molecular wires in molecular scale electronic devices, and they also serve as useful models for understanding analogous bulk polymers.
Thiophenol Protecting Groups for the Palladium-Catalyzed Heck Reaction: Efficient Synthesis of Conjugated Arylthiols
Hsung, Richard P.,Babcock, Jason R.,Chidsey, Christopher E. D.,Sita, Lawrence R.
, p. 4525 - 4528 (2007/10/02)
A variety of S-thiophenol protecting groups have been evaluated for the Heck reaction.Of these, the S-acetyl group appears to be the best suited for facile removal under mild conditions to provide the coresponding free thiols in high yields.
