NEW FERROCENOPHANES CONTAINING A HYDROPHOBIC, AROMATIC POCKET

Five novel ferrocenophanes which incorporate a hydrophobic, aromatic ' pocket' derived from alpha'-bis(4-hydroxyphenyl)-1,4-diisopropylbenzen e or a,alpha'-bis(4-aminopheny;)-1,4-diisopropylbenzene are synthesize d. Four of the new ferrocenophanes have been studied by cyclic voltamm etry. Solid-state structures of lipophilic ferrocenophane diamide 5, w hich has an aromatic 'pocket', and of the reactant 1,1'-di(hydroxymeth yl)ferrocene (13) have been determined by single-crystal X-ray diffrac tion analysis and are compared with those for other ferrocenophanes an d 1,1'-disubstituted ferrocenes respectively. 13 crystallizes in the s pace group P2(1)/c with a = 13.395(12) Angstrom, b = 7.714(5) Angstrom , c = 10.497(11) Angstrom, beta = 105.76(8)degrees, V = 1043.9 Angstro m(3), Z = 4, and R(R(w)) = 0.0323 (0.0354) for 999 reflections (F > 4. 0 sigma(F)). 5 crystallizes in the space group P2(1)/n with a = 10.948 (2) Angstrom, b = 12.387(2) Angstrom, c = 30.425(4) Angstrom, beta = 9 0.49(1)degrees, V = 4126.2 Angstrom(3), Z = 4, and R(R(w)) = 0.0611(0. 0723) for 3499 reflections (F > 4.0 sigma(F)). For 13, the structure c onsists of chains of molecules connected by hydrogen bonds with ferroc ene units on the outside of the chains and a hydrogen-bonded network o n the interior.