A novel C3v-symmetric molecular clip with tris(diamide) recognition sites on trindane platform for H2PO4− recognition. Issue 17 (25th April 2018)

• Record Type: Journal Article
• Authors: Kim, Gi-Dong; Bothra, Shilpa; Sahoo, Suban K.; Choi, Heung-Jin
• Is Part Of: Tetrahedron letters. Volume 59:Issue 17(2018)
• Page Start: 1679
• Page End: 1682
• Publication Date: 2018-04-25
• Subjects: C3v symmetric anion receptor -- Trindane -- H2PO4− recognition -- 1H NMR; DRYKWSQHRPVQKL-IREPWLAXSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.03.055
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A tripodal anion receptor2 with three diamide groups on trindane was synthesized. The anion recognition ability by2 was examined by 1 H NMR in DMSO- d 6 . Addition of H2 PO4 − guest caused downfield shifts of the amide-NH protons peaks of2 . Receptor2 formed a 1:1 complex with H2 PO4 − with binding constant ( K a ) of 244 M −1 . Abstract: To avoid the deprotonation events occurred in the receptor upon recognition of basic anions, a novel C3v -symmetric anion receptor2 with two amide groups appended in each arm was designed and synthesized by using the trindane tricarboxylic acid as tripodal molecular framework. The anion recognition ability by2 was examined by 1 H NMR titration study in DMSO- d 6, which revealed that the addition of H2 PO4 − guests caused substantial downfield shifts of the amide-NH protons peaks due to the formation of a host-guest complex in 1:1 binding stoichiometry with the estimated binding constant ( K a ) of 244 M −1 . No noticeable binding of2 was observed with other tested anions such as F −, Cl −, Br −, I −, NO3 − and HSO4 − under similar conditions.