Synthesis of Branch-Type Cyclophane Tetramers Having a Multivalently Enhanced Guest-Binding Ability - Advances in Chemical Engineering and Science

ACES > Vol.9 No.1, January 2019

Synthesis of Branch-Type Cyclophane Tetramers Having a Multivalently Enhanced Guest-Binding Ability ()

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DOI: 10.4236/aces.2019.91006 670 Downloads 1,459 Views Citations

Author(s)

Osamu Hayashida^*, Chihiro Nada, Shuhei Kusano

Affiliation(s)

Department of Chemistry, Faculty of Science, Fukuoka University, Nanakuma, Fukuoka, Japan.

ABSTRACT

A cationic branch-type cyclophane tetramer (1a) was synthesized by introducing three Boc-protected cyclophane derivatives into a N-acetylated tetraaza[6.1.6.1]paracy-clophane derivative as a core skeleton through DCC condensation, followed by removal of the external Boc-protecting groups. Cationic cyclophane tetramer 1a exhibited a high affinity toward an anionic and hydrophobic fluorescent guest, TNS, with binding constant of 4.8 × 10⁵ M^-1. This value of 1a was about 80-fold larger than that of the corresponding monomeric cyclophane for the identical guest, reflecting multivalent effect on the guest binding. As for electrostatic recognition, the obtained binding constant of 1a was one order of magnitude larger than that of an analogous anionic cyclophane tetramer (1b) for the identical guest. These enhanced guest-binding abilities of 1a were easily evaluated by fluorescence titration experiments.

KEYWORDS

Cyclophane, Host-Guest Chemistry, Multivalent Effect

Share and Cite:

Hayashida, O. , Nada, C. and Kusano, S. (2019) Synthesis of Branch-Type Cyclophane Tetramers Having a Multivalently Enhanced Guest-Binding Ability. Advances in Chemical Engineering and Science, 9, 76-86. doi: 10.4236/aces.2019.91006.

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