Precision host–guest chemistry of polyphenylene dendrimers

A Polyphenylene Dendrimer Drug Transporter with Precisely Positioned Amphiphilic Surface Patches

“…Polyphenylene dendrimers (PPDs) comprise semi‐rigid oligophenylene branches, where the scaffold forms a shell structure with end groups exclusively localized at the periphery . Therefore, compared with other dendrimers, PPDs adopt distinct globular architectures in solution with defined lipophilic cavities in their interior, which somewhat resemble protein‐like architectures.…”

Application of Rigidity‐Controlled Supramolecular Affinity Materials for the Gravimetric Detection of Hazardous and Illicit Compounds

“…In contrast to other dendrimers consisting of conformational flexible moieties, PPD derivatives exhibit a rigid and persistent shape because only confined rotation around the individual biaryl axis can occur. PPDs with tetraphenylmethane cores are quite rigid macromolecules with tetrahedral symmetry and have the possibility to generate more than one cavity within a single molecule . Recent studies of the dendrimer generations one to five with a tetraphenylmethane core by quartz crystal microbalances (QCMs) displayed excellent size exclusion effects .…”

“…[8] In contrastt oo ther dendrimersc onsistingo fc onformational flexible moieties, PPD derivatives exhibit ar igid and persistent shape because only confined rotation around the individual biaryl axis can occur.P PDs with tetraphenylmethanec ores are quite rigid macromolecules with tetrahedral symmetry and have the possibility to generate more than one cavity within as ingle molecule. [9] Recent studies of the dendrimer generations one to five with atetraphenylmethanec ore by quartz crystal microbalances (QCMs) displayed excellent size exclusion effects. [10] To further investigate host molecules with more than one cavity and explore the influence of intrinsic rigidity,w eu sed tetraphenylmethane 1 and the less-flexible 9,9'-spirobifluorene 2 (Scheme 1) as core building blocks for our study.A tf irst sight 2 differs from 1 by only two CÀCb onds, however,t he structuralf eatures change signif-icantly.A saresult of the additional bonds in 2,b oth diphenyl moieties are oriented orthogonal to each other.T his leads to limited rotation owing to the spiro centre, and therefore, in al ess flexible architecture.…”

Tuning Polarity of Polyphenylene Dendrimers by Patched Surface Amphiphilicity—Precise Control over Size, Shape, and Polarity

“…[ 18 ] Likewise, since the PPDs comprise defi ned voids they serve as receptors for guest molecules. [ 19 ] Their uptake can be analyzed by microbalance measurements or isothermal titration calorimetry (ITC) and leads to sensing devices for explosives. [ 20 ] Here, we consider another challenge for precision polymer synthesis: the control of amphiphilicity as an opportunity to mimic the delicate polar-and non-polar uptake, cellular toxicity as well as the integrity of biological barriers, i.e., the blood brain barrier.…”