Invited for the cover of this issue is the group of Takayuki Iwata, Mitsuru Shindo, and co-workers at Kyushu University. The image depicts ring-opening of triptycenes to afford corresponding anthrones by acid treatment. Read the full text of the article at 10.1002/chem.202104160.
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Intramolecular Hiyama Coupling: Synthesis of 1,8,13-Trisubstituted Chiral Triptycenes with Three Different Substituents by Intramolecular Substituent Transfer.
Chemistry
July 2023
Institute for Materials Chemistry and Engineering, Kyushu University, 6-1, Kasugako-en, Kasuga, 816-8580, Japan.
Article Synopsis
- The study discusses a method called Hiyama coupling that produces chiral triptycenes by transferring substituents from silicon between two parts of the molecule.
- The reaction relies on the proximity of these substituents, crucial for forming an oxy-palladacycle and activating the silyl group, which helps in a process called σ-bond metathesis.
- The final result includes various chiral triptycenes, with the study also achieving optical resolution for the first time, resulting in an optically active version of the compound.
Introduction of Triptycene with a Particular Substitution Pattern into Polymer Chains Can Dramatically Improve the Structural and Rheological Properties.
ACS Macro Lett
December 2021
Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan.
Although a large number of polymers that contain triptycene units in the main chains have been developed, no polymer design using 1,8-substituted triptycene has been reported to date. In this study, we investigated the properties of linear homo- and copolymers obtained by ring-opening polymerization of a triptycene monomer bearing a macrocyclic olefin linked at its 1,8-position and its copolymerization with cyclooctene, respectively. We found that the introduction of triptycene with this substitution pattern leads to nanoscale molecular ordering, thereby greatly improving the physical properties of the polymers.
View Article and Find Full Text PDFRetro-Friedel-Crafts-Type Acidic Ring-Opening of Triptycenes: A New Synthetic Approach to Acenes.
Chemistry
February 2022
Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580, Japan.
Invited for the cover of this issue is the group of Takayuki Iwata, Mitsuru Shindo, and co-workers at Kyushu University. The image depicts ring-opening of triptycenes to afford corresponding anthrones by acid treatment. Read the full text of the article at 10.
View Article and Find Full Text PDFRetro-Friedel-Crafts-Type Acidic Ring-Opening of Triptycenes: A New Synthetic Approach to Acenes.
Chemistry
February 2022
Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580, Japan.
The triptycene scaffold has been ring-opened by using a retro-Friedel-Crafts-type reaction under acidic conditions to give its corresponding anthrone product. 9-Hydroxytriptycenes and unsubstituted triptycene undergo ring-opening reaction under strongly acidic conditions, such as with TfOH. An investigation of the substitution effect has revealed that the electron-donating group on the arene moiety allows the reaction to proceed in the presence of a weaker acid, such as TFA.
View Article and Find Full Text PDFRegioselective One-Pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates.
Angew Chem Int Ed Engl
January 2017
Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580, Japan.
We developed the novel one-pot synthetic method of substituted triptycenes by the reaction of ynolates and arynes. This four-step process involves three cycloadditions and electrocyclic ring opening of the strained Dewar anthracene. Each of the three related but structurally distinct classes of nucleophiles (ynolate, enolate, and anthracenolate) reacts with o-benzyne in the same predictable manner controlled by chelation and negative hyperconjugation.
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