| Summary: | Abstract 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.
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