Abstract
Since the first preparation of triptycene, great progress has been made with respect to its synthesis and the understanding of its properties. Interest in triptycene-based systems is intense; in recent years, advances in the synthetic methodology and properties of new triptycenes have been reported by researchers from various fields of science. Here, an account of these new developments is given and placed in reference to earlier pivotal works that underpin the field. First, we discuss new approaches to the synthesis of new triptycenes. Progress in the regioselective synthesis of sterically demanding systems is discussed. The application of triptycenes in catalysis is also presented. Next, progress in the understanding of the relations between triptycene structures and their properties is discussed. The unique properties of triptycenes in the liquid and solid states are elaborated. Unique interactions, which involve triptycene molecular scaffolds, are presented. Molecular interactions within a triptycene unit, as well as between triptycenes or triptycenes and other molecules, are also evaluated. In particular, the summary of the synthesis and useful features will be helpful to researchers who are using triptycenes as building blocks in the chemical and materials sciences.
Highlights
Introduction0,20 ]-benzenoanthracene) isisThe parent parent triptycene triptycene(9,10-dihydro-9,10[1(9,10-dihydro-9,10[1′,2′]-benzenoanthracene) eye-catchanan eye-catching ing hydrocarbon a paddlewheel or propeller-shaped molecule.The characteristic hydrocarbon with with a paddlewheel or propeller-shaped molecule.The characteristic structure 3 carbon atoms3 carbon structure of triptycene is composed of threerings benzene rings two spatoms of triptycene is composed of three benzene joined byjoined two spby in a D3h in a D3h-symmetric with a barrelene core1). (Figure 1).symmetric structurestructure with a barrelene core
The triptycene molecule is characterized by: (a) high reactivity due to the presence of several chemically distinguishable positions on aromatic rings and bridgehead atoms; (b) limited conformational freedom and well-defined spatial arrangement of substituents, making the triptycene a rigid and robust scaffold; (c) internal molecular free volume (IMFV) [8] due to the inability of triptycene-containing structures to pack efficiently, which introduces shape-persistent local cavities; as well as (d) the ability of aromatic faces to participate in π-interactions; and (e) the chirality of triptycene derivatives, which can arise from appropriate substitution patterns
Another approach aimed at regioselective synthesis of triptycene derivatives was presented by the group in 2018—Shwartzen et al used cycloaddition of 1,4-benzoquinone to substituted anthracenes for the preparation of triptycenes functionalized with triflate or
Summary
(9,10-dihydro-9,10[1′,2′]-benzenoanthracene) eye-catchanan eye-catching ing hydrocarbon a paddlewheel or propeller-shaped molecule. (c) internal molecular free volume (IMFV) [8] due to the inability of triptycene-containing structures to pack efficiently, which introduces shape-persistent local cavities; as well as (d) the ability of aromatic faces to participate in π-interactions; and (e) the chirality of triptycene derivatives, which can arise from appropriate substitution patterns Due to these inherent characteristics, triptycene has become an exemplar of a multipurpose molecular scaffold [9,10,11,12,13,14,15,16,17,18,19,20,21,22]. This review can be helpful for researchers who wish to employ available synthetic scenarios for the preparation of triptycenes with the desired properties to be utilized in supramolecular chemistry, polymer science, and other fields
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