Chiral Triptycenes in Supramolecular and Materials Chemistry

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.

Chiral Triphenylacetic Acid Esters: Residual Stereoisomerism and Solid-State Variability of Molecular Architectures

“…100–101 °C). 20 [α] D 20 −5 ( c 1.26, CHCl 3 ). 1 H NMR (300 MHz, CDCl 3 ) δ 7.30–7.19 (m, 15H), 4.74 (td, J = 10.9, 4.3 Hz, 1H), 2.18–2.11 (m, 1H), 1.67–1.56 (m, 2H), 1.52–1.39 (m, 1H), 1.22–1.10 (m, 2H), 1.02–0.95 (m, 2H), 0.90 (d, J = 6.9 Hz, 3H), 0.88–0.74 (m, 1H), 0.62 (d, J = 6.9 Hz, 3H), 0.53 (d, J = 6.9 Hz, 3H).…”

“…In such cases, the chirality of the whole triptycene system is achieved by proper functionalization of benzene rings. 20 …”

Chiral Triptycenes: Concepts, Progress and Prospects

“…From synthesis to applications, achiral triptycenesa re well documented but chiral triptycenes have not been reviewed and only very recently as urvey has been published. [7] This Minireview coverst he concept and highlightst he development and applicationso fc hiral triptycenes. It also in-cludes clarifications of previously studied chiral triptycenes wherever available and shines alight on future prospects.…”

“…Recent results of chiral triptycenes has awakened them from a three decades sleep to become an important player in modern chemicals science. From synthesis to applications, achiral triptycenes are well documented but chiral triptycenes have not been reviewed and only very recently a survey has been published [7] . This Minireview covers the concept and highlights the development and applications of chiral triptycenes.…”

Triptycene derivatives as chiral probes for studying the molecular enantiorecognition on sub‐2‐μm particle cellulose tris(3,5‐dimethylphenylcarbamate) chiral stationary phase

“…Triptycenes can be chiral, [8][9][10][11][12][13][14][15] and, similarly to other popular chiral π-extended synthons, 16 can express chirality robustly, efficiently, and with relevance to chiroptical spectroscopies. In addition to their use in supramolecular and materials chemistry, asymmetric catalysis, and enantioseparation processes, chiral trypticenes can be used as attractive model systems in the frame of enantiorecognition studies.…”