Conformationally Mobile Acyclic Cucurbit[n]uril-Type Receptors Derived from an S-shaped Methylene Bridged Glycoluril Pentamer.

ABSTRACT: We report the synthesis of the conformationally mobile S-shaped glycoluril pentamer building block 3a and two new acyclic CB[n]-type receptors P1 and P2. P1 (9 mM) and P2 (11 mM) have moderate aqueous solubility but their host•guest complexes are poorly soluble. Host P1 does not undergo intermolecular self-association whereas P2 does (K_s = 189±27 M^-1). ¹H NMR titrations show that P1 and P2 are poor hosts toward hydrophobic (di)cations 6 - 11 (P1: K_a = 375-1400 M^-1; P2: K_a = 1950-19800 M^-1) compared to Tet1 and Tet2 (Tet1: K_a = 3.09 × 10⁶ to 4.69 × 10⁸ M^-1; T

SUBMITTER: Brady KG 

PROVIDER: S-EPMC7961848 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature