In order to maximize Coulombic interactions with positive guests, Cucurbit[8]uril (CB[8]) forms ternary complexes that distribute the positive charges over both portals of the macrocycle. However, our group showed that CB[8] and Pt(II) acetylides flanked by 4’-substituted terpyridyl (tpy) ligands form unprecedented 2:1 complexes with both Pt tpy units sitting on top of each other at the same CB[8] portal in a head-to-head (HH) fashion. We attribute the driving force to favorable ‘‘π–π’’ interactions between the extended aryl units, and to Pt–Pt interactions which counterweight Coulombic repulsion between the two positive guests. Herein we explore the supramolecular self-sorting properties of Pt tpy thiolates bearing a peptide backbone with a CGGGF sequence. This design allows the compound to associate with CB[8] or CB[7] at either the 4’-substituent of the tpy ligand or at the phenylalanine residue. Assembly CB[8]Pt●(Pt●1)2 adopts the expected HH arrangement permitting the terminal phenyl moieties to recognize other CB[n] molecules. In fact, it can bind up to two additional molecules of CB[7] to afford assembly CB[8]Pt●(Pt●1)2●CB[7]Phe2. Likewise, it can also bind up to CB[8]. In this case, necklace CB[8]Pt●(Pt●1)2●CB[8]Phe is obtained with two CB[8] units, one that forms a “stacked 2:1” dimer of Pt complexes, and the other a HT assembly with the phenylalanine residues.

Self-sorting of ditopic Pt(II) terpyridyl thiolate complexes with cucurbiturils

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.