Molecular Recognition Properties of Biphen[4]arene. Issue 23 (22nd November 2016)

• Record Type: Journal Article
• Authors: Ma, Suxiang; Chen, Huanqing; Li, Jian; Jia, Xueshun; Li, Chunju
• Is Part Of: Chemistry, an Asian journal. Volume 11:Issue 23(2016)
• Page Start: 3449
• Page End: 3453
• Publication Date: 2016-11-22
• Subjects: biphen[n]arenes -- macrocyclic hosts -- molecular recognition -- supramolecular chemistry; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201601373
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: Biphen[ n ]arenes ( n =3, 4) are a new family of macrocyclic hosts. Here, we describe the molecular recognition behavior of hydroxylated biphen[4]arene (OHBP4) for the first time. A series of cationic guests with different sizes and shapes, including quaternary ammonium salts (1⋅ PF6 and2⋅ PF6 ), pyridinium‐based guests (3⋅ 2 PF6 –6⋅ 2 PF6 ), and cobaltocenium hexafluorophosphate (7⋅ PF6 ), were chosen as model guest molecules. OHBP4 exhibits good selectivity towards the 2, 7‐dibutyldiazapyrenium bis(hexafluorophosphate) (4⋅ 2 PF6 ) axle to form a [2]pseudorotaxane‐type complex. In contrast, hydroxylated biphen[3]arene (OHBP3) cannot bind with this big guest. In addition, OHBP4 strongly interacts with adamantane derivative2⋅ PF6 and cobaltocenium7⋅ PF6, which have tridimensional shape and relatively large size. The association constant of the7 + ⊂OHBP4 complex in 1:1 (v/v) [D6 ]acetone/CD2 Cl2 solution is up to 3100±300 m −1 . Abstract : Biphen[4]arene recognizes guests : Molecular recognition behavior of hydroxylated biphen[4]arene (OHBP4) was demonstrated for the first time. OHBP4 exhibits strong affinities towards 2, 7‐dibutyldiazapyrenium4⋅ 2 PF6, adamantane derivative2⋅ PF6, and cobaltocenium7⋅ PF6 to form inclusion complexes. The association constant of7 + ⊂OHBP4 in 1:1 (v/v) [D6 ]acetone/CD2 Cl2 solution is up to 3100±300 m −1 .