To diphenylglycoluril (2), four aliphatic chains were attached, each with a vanillyl alcohol group at the end as discussed by the authors, and three of them cyclized to form a cyclotriveratrylene unit.
Abstract:
To diphenylglycoluril (2), four aliphatic chains were attached, each with a vanillyl alcohol group at the end. In an acid-catalyzed reaction, three of the vanillyl alcohol groups cyclize to form a cyclotriveratrylene unit. The resulting compound (3) has a well-defined cavity and a free, func- tionalized arm. Cyclization of four vanillyl alcohol groups (5) does not occur, probably for steric reasons.
TL;DR: Hemmicryptophanes are revealed to be inherently chiral ditopic host compounds, able to encapsulate various guests, including charged and neutral species, and enter the field of stimuli-responsive supramolecular systems exhibiting controlled functions.
TL;DR: A review of the recent developments of the chemistry of cyclotriveratrylenes and cryptophanes, and their use in the study of host-guest interactions is given in this paper.
TL;DR: A novel class of chiral hemicryptophane hosts has been synthesized in diastereoisomerically pure form and displayed two pairs of mirror-image CD spectra, which were used to determine their absolute configuration.
TL;DR: The heteroditopic hemicryptophane 1, which bears a tripodal anion binding site and a cation recognition site in the molecular cavity, proved to be an efficient ion-pair receptor.
TL;DR: Determination of the activation parameters provides evidence for a concerted, rather than a stepwise, interconversion mechanism with entropies of -243 and -272 J mol (-1) K(-1) for (P)-(S,S,Lambda)-3 and (M-S, S-S)-4, respectively.