Triptycenes are an intriguing class of organic molecules with several unusual characteristics, such as a propeller‐like shape, saddle‐like cavities around a symmetrical scaffold, a rigid π‐framework. They have been extensively studied and proposed as key synthons for a variety of applications in supramolecular chemistry and materials science. When decorated with an appropriate substitution pattern, triptycenes can be chiral, and, similarly to other popular chiral π‐extended synthons, can express chirality robustly, efficiently, and with relevance to chiroptical spectroscopies. This minireview highlights and encompasses recent advances in the synthesis of chiral triptycenes and in their introduction as molecular scaffolds for the assembly of functional supramolecular materials.

A chiral cage is proposed as an effective chiroptical sensor for perrhenate (surrogate for 99TcO4-) in water, fruit juice and artificial urine medium. The key mechanism for the chiroptical sensing...

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The electroreduction mechanism of 1‐Br‐2‐naphtol and 1‐I‐2‐naphtol, and of two inherently chiral BINOL derivatives ([1,1′‐Binaphthalene]‐2,2′‐diol, 6,6′‐dibromo and 1,1′‐Binaphthalene,6,6′‐dibromo‐2,2′‐dimethoxy; in the following named P1 and P2, respectively), is characterized by means of an integrated electrochemical and theoretical approach. The experimental characterization is based on cyclic voltammetry measurements. The experimental results indicate that the carbon halogen bond dissociates, following the electron uptake, with the formation of an insoluble final product (electro‐polymerization). The reduction mechanism is assessed and disassembled at a molecular level by using DFT based quantum mechanical calculations. Both steady state, equilibrium, and kinetic (molecular dynamics, MD, DRC calculations) properties are calculated. A consistent picture is obtained by the comparison between experimental and theoretical results, indicating that the carbon‐halogen bond dissociates following the first electron uptake, with a stepwise mechanism.