Molecular Recognition Properties of Biphen[4]arene

Suxiang Ma; Huanqing Chen; Jian Li; Xueshun Jia; Chunju Li

doi:10.1002/asia.201601373

Molecular Recognition Properties of Biphen[4]arene

Chem Asian J. 2016 Dec 6;11(23):3449-3453. doi: 10.1002/asia.201601373. Epub 2016 Nov 22.

Authors

Suxiang Ma^{1

2}, Huanqing Chen², Jian Li², Xueshun Jia^{2

3}, Chunju Li^{1

2}

Affiliations

¹ School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, 201418, P.R. China.
² Department of Chemistry, Center for Supramolecular Chemistry and Catalysis, Shanghai University, Shanghai, 200444, P.R. China.
³ State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, P.R. China.

PMID: 27759950
DOI: 10.1002/asia.201601373

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 and 2⋅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 derivative 2⋅PF₆ and cobaltocenium 7⋅PF₆ , which have tridimensional shape and relatively large size. The association constant of the 7⁺ ⊂OHBP4 complex in 1:1 (v/v) [D₆ ]acetone/CD₂ Cl₂ solution is up to 3100±300 m^-1 .

Keywords: biphen[n]arenes; macrocyclic hosts; molecular recognition; supramolecular chemistry.