COMPLEXATION WITH DIOL HOST COMPOUNDS .15. CRYSTALLINE INCLUSION-COMPOUNDS OF SUBSTITUTED 2,2'-BIS(9-HYDROXYFLUOREN-9-YL)BIPHENYLS - SYNTHESIS, X-RAY CRYSTAL-STRUCTURES AND THERMAL-ANALYSIS STUDY OF INCLUSION-COMPOUNDS WITH BUTYRONITRILE, CYCLOHEXANONE, CYCLOPENTANOL AND DIMETHYLFORMAMIDE

The syntheses of 2,2'-bis(2,7-di-tert-butyl-9-hydroxyfluoren-9-yl)biphenyl (2), 2,2'-bis(2,7-dichloro-9-hydroxyfluoren-9-yl)biphenyl (3) and 2,2'-bis(2,7-dibromo-9-hydroxyfluoren-9-yl)biphenyl (4) are reported. Inclusion compounds were prepared with these hosts: 5 = 2.butyronitrite (1:1), 6 = 3.cyclohexanone (1:2), 7 = 3.cyclopentanol (1:2), 8 = 4.dimethylformamide (1:2). Crystal data: 5, monoclinic, C2/c with a = 17.174(2), b = 17.985(3), c = 17.333(3) angstrom, beta = 113.73(1)-degrees, Z = 4, D(c) = 1.10 g cm-3; 6, monoclinic, P2(1)/n with a = 15.048(3), b = 16.106(4), c = 19.10(1) angstrom, beta = 112.97(4)-degrees, Z = 4, D(c) = 1.32 g cm-3; 7, monoclinic, P2(1)/c with a = 14.576(2), b = 15.783(4), c = 19.561 (4) angstrom, beta = 111.72(1)-degrees, Z = 4, D(c) = 1.31 g cm-3; 8, triclinic, P1BAR with a = 11.52(1), b = 11.825(1), c = 17.836(1) angstrom, alpha = 79.19 (5), beta = 71.15 (7), gamma = 60.85 (7)-degrees, Z = 4, D(c) = 1.62 g CM-3 . Final R values for the four structures were 0.071, 0.062, 0.077 and 0.096 for 2489, 3270, 3432 and 3802 reflections, respectively. Host ... guest hydrogen bonds are observed in all four structures and there is an intramolecular hydrogen bond in the hosts 5-7. In addition, in compounds 6-8 there are a number of O ... Cl, Cl ... Cl, N ... Br and Br ... Br interactions. Thermal analysis was used to study the binding of the guest molecules and indicated that the guests in 5-7 were more strongly held than that in 8.