255850-24-9Relevant articles and documents
Functionalized calix[4]resorcinarene cavitands. Versatile platforms for the modular construction of extended molecular switches
Azov, Vladimir A.,Schlegel, Anna,Diederich, Francois
, p. 1926 - 1940 (2007/10/03)
We report the synthesis and investigation of the vase-kite conformational switching of bridged calix[4]resorcinarene-based cavitands bearing iodo or ethynyl substituents on the upper rim of the cavity. These reactive centers make the cavitands versatile p
Assembly and Binding Properties of Osmate Ester-Bridged Binuclear Macrocycles
Jeong, Kyu-Sung,Cho, Young Lag,Chang, Sung-Youn,Park, Tae-Yoon,Song, Jung Uk
, p. 9459 - 9466 (2007/10/03)
Osmium (VI)-bridged macrocycles 1a-c, 2, and 3 assemble spontaneously when osmium tetraoxide, olefins, and L-shaped bispyridyl ligands are mixed in CHCl3. The macrocycles possess well-defined square or rectangular cavities enclosed by aryl walls and act as host molecules. Hydrogen-bond donors on the inner surface of the hosts offer binding sites to acceptors of guests with complementary dimensions. The host 1a binds adipamide G2 (Ka = 3.6 × 104 M-1) and terephthalamide G6 (Ka = 2.0 × 104 M-1), while it binds negligibly (Ka -1) benzamide G5, isophthalamide G9, or 1,4-naphthalenedicarboxamide G10. The larger hosts 2 and 3 bind the longer guests biphenyldicarboxamide G12 and terphenyldicarboxamide G17, respectively, but shorter guests such as adipamide G2 and terephthalamide G6 are not well-bound (Ka -1). Hosts 1a-c with different remote substituents (H, OMe, NO2) but identical cavity size were prepared and their binding affinities were measured. The relative binding affinities of the hosts 1a-c to the keto amide G19, ester amide G20, and diester G21 are in the order of 1c (NO2) ? 1a (H) > 1b (OCH3). The substituent effects on the binding strength are interpreted in terms of the electron density at the pyridine nitrogen of the hosts and its effect on bifurcated hydrogen bonding.