110598-30-6Relevant articles and documents
Conductance of single triangular dehydrobenzo[12]annulene derivative bridged between Au electrodes
Kiguchi, Manabu,Tahara, Kazukuni,Takahashi, Yuuta,Hasui, Kensuke,Tobe, Yoshito
, p. 788 - 789 (2010)
A triangular dehydrobenzo[12]annulene (DBA) molecule bridged between Au electrodes was investigated by scanning tunneling microscopy break junction technique. The conductance of the single DBA molecule was determined to be 2.5 × 10-5 G0/s
Linear free-energy correlation analysis of the electronic effects of the substituents in the Sonogashira coupling reaction
Gottardo, Christine,Kraft, Thomas M.,Hossain, M. Selim,Zawada, Peter V.,Muchall, Heidi M.
, p. 410 - 415 (2008)
Relative rate constants (krel) for the Sonogashira coupling were determined in competitive reactions between iodobenzene and a series of para- and meta-substituted iodobenzenes and compared to the charge on iodine and the z-component of the qua
Catalytic Activation of Trimethylsilylacetylenes: A One-Pot Route to Unsymmetrical Acetylenes and Heterocycles
Lasányi, Dániel,Mészáros, ádám,Novák, Zoltán,Tolnai, Gergely L.
, p. 8281 - 8291 (2018/06/11)
For the synthesis of unsymmetrical acetylenes, a Sonogashira coupling-deprotection-Sonogashira coupling reaction sequence is often used. Removal of protecting groups requires harsh conditions or an excess of difficult to handle and expensive reagents. Herein, we disclose a novel catalytic method for the selective deprotection of trimethylsilylacetylenes in Sonogashira reaction. The reagent hexafluorosilicic acid, an inexpensive nontoxic compound, was used to promote the selective desilylation. This method enables the efficient synthesis of unsymmetric acetylenes with other silylated functional groups present. Further possibilities of the method were explored by synthesis of heterocycles.
Determining the regioregularity in alkyne polycarbodiimides and their orthogonal modification of side chains to yield perfectly alternating functional polymers
Budhathoki-Uprety, Januka,Reuther, James F.,Novak, Bruce M.
, p. 8155 - 8165 (2013/01/15)
To understand the structure-property relationship in functional macromolecules through side chain modulation, both the accurate determination of the position of modifiable groups along the polymer chain and their subsequent modifications using high fidelity methods are crucial. In this report, the polymer microstructure of a helical alkyne polycarbodiimide has directly been probed through 15N NMR spectroscopy on isotopic labeled poly(N-(3-ethynylphenyl)-15N′-hexyl)carbodiimide and found to be a highly regioregular polymer structure. This polymer undergoes facile and quantitative CuAAC "click" chemistry, yielding perfectly alternating functional polymers. Advances have been made through the synthesis of new optically active alkyne polycarbodiimides with two independently modifiable pendant groups per repeat unit of polymers. Orthogonal postmodifications of the pendant groups were then performed to incorporate two different sets of small molecules in the repeat unit of polymers in a controlled manner and under mild reaction conditions using either sequential CuAAC "click" reactions when two dissimilar alkyne groups are present or a combination of CuAAC and thiol-ene click chemistries when pendant groups bear alkyne and vinyl moieties.