Chiral self-sorting is intricately connected to the complicated chiral processes observed in nature and no artificial systems of comparably complexity have been generated by chemists.H owever,o nly af ew examples of purely organic molecules have been reported so far,w here the selfsorting process could be controlled. Herein, we describe the chiral self-sorting of large cubic [8+ +12] salicylimine cage compounds based on ac hiral TBTQ precursor.O ut of 23 possible cage isomers only the enantiopure and am eso cage were observed to be formed, whichhave been unambiguously characterized by single crystal X-raydiffraction. Furthermore, by careful choice of solvent the formation of meso cage could be controlled. With internal diameters of d in = 3.3-3.5 nm these cages are among the largest organic cage compounds characterizedand show very high specific surface areas up to approx. 1500 m 2 g À1 after desolvation.

Porous shape-persistent organic cages have become the object of interest in recent years because they are soluble and thus processable from solution. A variety of cages can be achieved by applying dynamic covalent chemistry (DCC), but they are less chemically stable. Here the transformation of a salicylimine cage into a quinoline cage by a twelve-fold Povarov reaction as the key step is described. Besides the chemical stability of the cage over a broad pH regime, it shows a unique absorption and emission depending on acid concentration. Furthermore, thin films for the vapor detection of acids were investigated, showing color switches from pale-yellow to red, and characteristic emission profiles.

Charge transfer (CT) crystals of an electron donor and an acceptor have electronic properties that are different from the two pure components. Despite the great potential of such CT crystals have for organic electronics, the control of the spatial arrangement of donor and acceptor molecules in the cocrystals plays a crucial role for the charge transfer itself or, for example, for charge transport. In most cases, by changing e.g. the acceptor components, various cocrystals are accessible but in almost all cases with different packing motifs and thus crystallographic parameters. This makes a direct and systematic comparison of different donor–acceptor pairs difficult or even impossible. On the basis of a triptycene end-capped dimethoxy-quinoxalinophenanthrophenazine (QPP-OMe) as a donor with six small electron-deficient molecules as acceptors, an isostructural packing could be realized, where the QPP-OMe donor is forming voids with nearly the same orientation and size to enclathrate the acceptor molecules, as has been revealed by single-crystal X-ray diffraction. The CT complexes were studied spectroscopically, supported by density functional theory calculations.

We report on the impact of the central heteroatom on structural, electronic, and spectroscopic properties of a series of spirofluorene‐bridged heterotriangulenes and provide a detailed study on their aggregates. The in‐depth analysis of their molecular structure by NMR spectroscopy and X‐ray crystallography was further complemented by density functional theory calculations. With the aid of extensive photophysical analysis the complex fluorescence spectra were deconvoluted showing contributions from the peripheral fluorenes and the heteroaromatic cores. Beyond the molecular scale, we examined the aggregation behavior of these heterotriangulenes in THF/H2O mixtures and analyzed the aggregates by static and dynamic light scattering. The excited‐state interactions within the aggregates were found to be similar to those found in the solid state. A plethora of morphologies and superstructures were observed by scanning electron microscopy of drop‐casted dispersions.

The ORCID identification number(s) for the author(s) of this article can be found under https://doi.org/10.1002/aelm.202100400.