LAUSR

Among the various types of chirality (central, axial, helical, planar…), that inherent to Möbius topology remains almost unex-plored, partly due to the difficulty to access Möbius compounds. Over the last decade, [28]hexaphyrins have revealed among the best candidates to build on Möbius aromaticity. Whereas their flexibility needs to be controlled to get P/M twist enantioselectivity, it could be of great interest to sustain dynamic chirality transfer. In this context, we report herein the first example of a Möbius aromatic ring capped by a cavity, consisting in a Möbius [28]hexaphyrin doubly-linked to an α-cyclodextrin. This unique design affords a "totem" of three different chirality elements arising from the cyclodextrin (fix central chirality), the bridging pattern (dynamic planar chirality) and the hexaphyrin (dynamic topological chirality). Chirality transfers (see TOC graphic) are characterized by a stereospecific planar-to-topological communication (diast. excess > 95 %; the highest asymmetric selectivity reported to date for a Möbius ring) combined to a stereoselective central-to-planar communication (up to 60 % diast. excess). Interestingly, the stereoselectivity is remotely controlled by coordination of an achiral effector to the hexaphyrin, increasing up to five times the chiroptical response of the Möbius aromatic π-system. These results highlight the advantageous use of dynamic chirality transfers to further incorporate Möbius chirality and aromaticity into all kind of stimuli responsive devices.