Treatment of phosphodihydrazides PhP(Y)(N(CH3)NH2)(2) (4a, Y = S; 4b, Y = O) with either the 3,3’-[(3-oxapentane-1,5-diyl)dioxy]bis(2-hydroxybenzaldehyde) (6) or 3,3’-[(3,6-dioxaoctane-1,8-diyl)dioxy]bos(2-hydroxybenzaldehyde) (7) gave rise to macrocycles 8a,b, 9a,b, 10a, and 11a resulting from cyclocondensation between 1 equiv of each partner. Similar reactions in the presence of Ba(CF3SO3)(2) as a template salt led either to 1/1 complexes (1 macrocycle/1 Ba(CF3SO3)(2)) 12 and 13 or to a sandwich complex, 14. 14 crystallized in the monoclinic space group P2(1/c) with a = 14.507 (3) Angstrom, b = 15.776 (4) Angstrom, c = 14.513 (4) Angstrom, beta = 109.44 (2)degrees, Z = 2, and V = 3132 (1) Angstrom(3). Bimacrocycles 15a,b can be obtained by reacting the dialdehyde 7 with phosphotrihydrazide (Y)P[N(CH3)-NH2](3) (5a, Y = S; 5b, Y = O). Reaction of the monofunctionalized phosphorus macrocycle 18 with the sodium salt of a phosphodihydrazone, PhP(S)[N(Me)N=CHC6H4ONa](2) (19), afforded another type of bimacrocyclic species, 20, containing five phosphorus atoms. A Staudinger reaction between the phosphine 22 bearing a crown ether unit and the diazido tetraphosphorus-containing macrocycle 21 led to a trimacrocycle, 24, possessing one central phosphorus macrocycle and two crown ethers. Similarly the reaction between phosphine 22 (4 equiv) with the tetraazido tetraphosphorus-containing macrocycle 25 gave the pentamacrocyclic species 27.