Premium
Cooperative Self‐Assembly of a Quaternary Complex Formed by Two Cucurbit[7]uril Hosts, Cyclobis(paraquat‐ p ‐phenylene), and a “Designer” Guest
Author(s) -
Tootoonchi Mohammad Hossein,
Sharma Gaurav,
Calles Jonathan,
Prabhakar Rajeev,
Kaifer Angel E.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201606038
Subject(s) - chemistry , supramolecular chemistry , cyclophane , aqueous solution , self assembly , host–guest chemistry , paraquat , electrospray mass spectrometry , stereochemistry , crystallography , combinatorial chemistry , mass spectrometry , molecule , electrospray , organic chemistry , chromatography
Abstract The self‐assembly in aqueous solution of the well‐known cyclophane, cyclobis(paraquat‐p‐phenylene) (BB 4+ ), and two cucurbit[7]uril (CB7) hosts around a simple hydroquinol‐based, diamine guest (GH 2 2+ ) was investigated by 1 H NMR and electronic absorption spectroscopies, electrospray mass spectrometry and DFT computations. The formation of a quaternary supramolecular assembly [GH 2 2+ ⋅BB 4+ ⋅ (CB7) 2 ] was shown to be a very efficient process, which takes place not only because of the attractive forces between each of the hosts and the guest, but also because of the lateral interactions between the hosts in the final assembly. This complementary set of attractive interactions results in clear cooperative binding effects that help overcome the entropic barriers for multiple component assembly.