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Inclusion Compounds of Bulky Binaphthyl-type Bis-fluorenol Hosts

“…However, with regard to the variety and number of inclusion compounds, they are little influenced by individual substitutions, although these do provide an indication of the effectiveness of the basic host framework. This particular behavior is probably due to the twisted conformation of the basic host skeleton being stabilized by a strong intramolecular hydrogen bond between the fluorenyl hydroxy groups, as is found in all the previous [15,16] and currently solved structures of respective inclusion compounds, except for 3a, which seems to be a very specific case. Nevertheless, the type of substitution shows differences in the stoichiometric host:guest ratios for the same guests and also in the modes of supramolecular interaction of the inclusion structures, including, aside from conventional hydrogen bonding [23], specific CZH· · ·p(aryl) [18], CZH· · ·halogen [20,25] and halogen· · ·halogen contacts [19,20,23].…”

“…The host compounds 1-4 were synthesized from 3,3 0 -dibromo-2,2 0 -binaphthyl and 9-fluorenone, 2,7-dichloro-9-fluorenone, 2,7-dibromo-9-fluorenone or 2,7-di-t-butyl-9-fluorenone using a lithium organic reaction in accordance with a literature procedure [15,16]. The inclusion compounds were obtained by recrystallization of the host compound from the respective guest solvent.…”

“…The host compound 1, which forms a 1:3 (host:guest) clathrate with acetone, has been found to reveal promising supramolecular materials behavior in vapor sensing of this solvent [15]. Moreover, crystalline inclusion compounds of 2 and 3 with acetone have been studied by X-ray analysis and also by solid-state NMR, showing differently bound guest molecules [16].…”

Interplay of Thermochemistry and Structural Chemistry, the Journal (Volume 13, 2002) and the Discipline

“…In the next paper, Hasse et al [97] discussed complexes formed with 3,3 -bis(9-hydroxy-9-fluorenyl)-2,2 -binaphthyl. While the enthalpies of formation of 9,9 -bianthryl and 9,9 -biphenanthryl have long been known, there are no corresponding data for the enthalpies of formation of the isomeric 1,1 ; 1,2 and 2,2 -binaphthyls.…”

Inclusion of picolines by a substituted binaphthyl diol host: selectivity and structure

“…14 This compound was also analysed by solid-state NMR, which allowed the identication of differently bound guest acetone molecules from distinct chemical shis obtained from the inclusion compounds. 15 In this work, we analyse the structures obtained with the three isomers of picoline and we establish the selectivity proles of this host by competition experiments with the guestpairs 2PIC/3PIC, 2PIC/4PIC and 3PIC/4PIC. The atomic numbering is shown in Scheme 1.…”