Tandem tautomerization-trapping of isomeric mixtures of tris(N-salicylideneamine)s facilitated access to a new class of discotic molecules that are geometrically analogous to 2,6,10-trisubstituted triphenylenes. The shape and electrostatic complementarity associated with the molecular C3 symmetry assists cofacial stacking of pi-faces to afford either infinite one-dimensional columns or discrete dimeric capsules. Structural reinforcement achieved by such interlocked geometry resulted in significant fluorescence enhancement upon aggregation in solution, as determined by dynamic light scattering and fluorescence spectroscopy.
Correlated bond rotations within biconcave molecules that comprise a semirigid C3‐symmetric core and pendant m‐terphenyl groups (see figure) assist mechanical coupling between the two vertices such that structural changes on one side of the molecule are effectively transmitted to the other side. Self‐assembly of one such compound affords a nonporous solid from which entrapped guests can completely escape in the absence of channels that connect interstitial voids.
Controllable switching between two stable conformations of inherently dynamic chemical architectures can be exploited as a potent signal transduction mechanism for chemical sensing. In this article are highlighted selected examples of this emerging class of shape-adaptive molecular sensors that are built with simplicity in their operating principles but with diversity in their structural designs.
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