Crystalline inclusion compounds of new elongated bisfluorenol hosts with protic guest molecules

Versatility in Complexation of Aprotic Guest Molecules by Terphenyl-Based Bisfluorenol Hosts. Structural Modes in the Crystalline Inclusions and of a Guest-Free Host Compound

“…In summary, it is shown that considering also the previously demonstrated inclusion behavior of 1 and 2 with protic guest molecules, 19 this particular type of terphenyl host may not only be rated as a simple structural modification of the well-known biphenyl analogues 18 but also seem to open up development of a new model of versatile host compound, promising usefulness in practical crystal engineering in particular of supramolecular inclusion formation.…”

“…19 Thus, the restricted conformational flexibility of the host molecular framework attributed to intramolecular C−H···O hydrogen bonding and π···π arene interactions being unaffected not by the presence of protic or nonprotic guest solvents becomes apparent as a true structural characteristic of this host type. Whether it will ever be possible to break open this seemingly resistant host conformation under the influence of a particularly strong interacting guest species remains to be seen.…”

Crystal structure of 2,2′′-bis(2,7-dichloro-9-hydroxy-9H-fluoren-9-yl)-1,1′:4′,1′′-terphenyl triethylamine trisolvate

“…Interactions involving the chlorine atoms are not perceptible. A comparative consideration regarding the geometric features of the diol molecule in the present structure and the solvent-free structure of the corresponding unsubstituted compound (I) and its derivatives bearing alkyl groups in the 2-and 7-positions of the fluorenyl moieties as well as a variety of their inclusion structures (Klien et al 2013(Klien et al , 2014, reveals restricted conformational flexibility. This means that neither the presence of substituents nor the nature of the included solvent species markedly affect the conformation of the diol molecule.…”

“…Both exchange of the central biphenyl axis for a 1,1 0 :4 0 ,1 00 -terphenyl moiety [cf. (I)] (Klien et al, 2013(Klien et al, , 2014 as well as the addition of substituents to the lateral fluorenyl groups in a representative molecule (Bourne et al, 1994;Caira et al, 1997;Weber et al, 2002) have been performed in order to exercise potential control of the molecular packing in the crystal and thus on the inclusion behavior towards selected guests. Along these lines, aside from conventional hydrogen bonding (Braga & Grepioni, 2004), ClÁ Á ÁCl supramolecular interactions (Awwadi et al, 2006) have recently been found to support crystal engineering of an intended lattice structure (Metrangolo et al, 2008;Mukherjee et al, 2014).…”

“…A search of the Cambridge Structural Database (Groom & Allen, 2014) for the 2,2 00 -disubstituted p-terphenyls yielded eleven hits, namely 4,4 000 '-bis(4-methoxybenzoyl)-1,1 0 :2 0 ,1 00 :4 00 ,1 000 :2 000 ,1 000 '-quinquephenyl (Debroy et al, 2009), 2,2 00 -bis(bromomethyl)-p-terphenyl (Jones & Kuś, 2005), 2,2 00dimethyl-p-terphenyl (Lunazzi et al, 2005), 2 0 ,4 00 ,2 000 -quinquephenyl (Toussaint, 1966), 9,9 0 -(1,1 0 :4 0 ,1 00 -terphenyl-2,2 00diyl)bis(9H-fluorene-9-ol) bis(diethylamine) clathrate (Klien et al, 2013), 9,9 0 -(1,1 0 :4 0 ,1 00 -terphenyl-2,2 00 -diyl)bis(9H-fluorene-9-ol) bis(propan-1-ol) clathrate (Klien et al, 2013), 9,9 0 -(1,1 0 :4 0 ,1 00 -terphenyl-2,2 00 -diyl)bis(9H-fluorene-9-ol) bis(butan-1-ol) clathrate (Klien et al, 2013), 9,9 0 -(1,1 0 :4 0 ,1 00 -terphenyl-2,2 00 -diyl)bis(9H-fluorene-9-ol) bis(ethanol) clathrate (Klien et al, 2013), 9,9 0 -(1,1 0 :4 0 ,1 00 -terphenyl-2,2 00 -diyl)bis(2,7-di-t-butyl-9H-fluorene-9-ol) bis(propan-1-ol) clathrate (Klien et al, 2013), 9,9 0 -(1,1 0 :4 0 ,1 00 -terphenyl-2,2 00 -diyl)bis(2,7-di-t-butyl-9Hfluorene-9-ol) bis(diethylamine) clathrate (Klien et al, 2013), 9,9 0 -(1,1 0 :4 0 ,1 00 -terphenyl-2,2 00 -diyl)bis(2,7-di-t-butyl-9H-fluor- x; y; z À 1; (ii) Àx þ 1; Ày þ 2; Àz þ 1; (iii) Àx þ 1; Ày þ 1; Àz þ 1; (iv) Àx þ 2; Ày þ 1; Àz; (v) Àx þ 1; Ày þ 1; Àz.…”