ABSTRACT: The self-assembled heterocapsule 1.2, which is formed by the hydrogen bonds of tetra(4-pyridyl)-cavitand 1 and tetrakis(4-hydroxyphenyl)-cavitand 2, encapsulates 1 molecule of guests such as 1,4-diacetoxybenzene 3a, 1,4-diacetoxy-2,5-dimethylbenzene 3b, 1,4-diacetoxy-2,5-dialkoxybenzenes (3c, OCH(3); 3d, OC(2)H(5); 3e, OC(3)H(7); 3f, OC(4)H(9); 3g, OC(5)H(11); 3h, OC(6)H(13); 3i, OC(8)H(17)), 1,4-diacetoxy-2,5-difluorobenzene 4a, and 1,4-diacetoxy-2,3-difluorobenzene 4b. The X-ray crystallographic analysis of 3c@(1.2) showed that the acetoxy groups at the 1,4-positions of 3c are oriented toward the 2 aromatic cavity ends of 1.2 and that 3c can rotate along the long axis of 1.2. Thus, the 1.2 (stator) with the encapsulation guest (rotator) behaves as a supramolecular gyroscope. A variable t
