Crystalline Hosts Based on the Assembly of Anthracene and Bulky Alcoholic Groups – Host Synthesis, Complex Formation, and X-ray Crystal Structures of Several Inclusion Compounds

Abstract

A series of new clathrate host molecules (1–10) containing two diarylhydroxymethyl groups attached to different positions (1,5 or 1,8) of a basic anthracene construction unit have been synthesized. Their clathrate formation properties with a variety of organic guests, including amines, alcohols, ketones, and other dipolar aprotic compounds or aromatic hydrocarbons are reported (143 examples of clathrates). The inclusion properties and the clathrate stoichiometries depend in a systematic manner on the structure of the host molecules. The crystal structures of six selected clathrates of different classes of compound have been determined by X‐ray diffraction.

Inclusion Compounds of Diol Hosts Featuring Two 9-Hydroxy-9-fluorenyl or Analogous Groups Attached to Linear Spacer Units

“…(1 h, 15 Torr, room temperature) refer to what we consider a ''stable clathrate''. [49] Inclusion Properties Thanks to their structural design, pronounced inclusion behavior is to be expected for potential host compounds [a] See the Exp. Sect.…”

Crystalline inclusion compounds of a new diol host featuring a combination of anthracene and 9-fluorenol units

“…The rigid spacers are mostly phenylene and ethynylene units or combinations of these groups, respectively (7)(8)(9). Anthracene moieties with different substitution patterns, especially the 9,10-anthrylene segment that gives rise to a linear structure, have also been used (6,10). A particular host compound of this type bearing two bulky 9-hydroxy-9-fluorenyl residues linked by a 9,10-diethynylene elongated anthracene spacer (1) (Scheme 1) as well as its clathrate behaviour has been recently reported (11,12).…”

Solvent-Free Synthesis and Crystal Structure of 9,10-Dihydro-9,10-diphenylanthracene-2,3,6,7-tetraol Inclusion Compounds

“…Crystalline hosts containing anthracene subunits have proven highly efficient in the formation of crystalline inclusion compounds because of their p-stacking and spatial shielding effects [16]. Depending on the positions of substituents attached to the anthracene moiety, they constitute a family of clathrate host molecules with different molecular geometry and supramolecularity [17][18][19].…”