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Georgiadis, T.M., Georgiadis, M.M. and Diederich, F. (1991) Synthesis and Complexation Properties of a Water-Soluble Optically Active Cyclophane Incorporating a 4-Naphthyl-1,2,3,4-Tetrahydroisoquinoline Unit as a Chiral Spacer. The Journal of Organic Chemistry, 56, 3362-3369.
https://doi.org/10.1021/jo00010a034

has been cited by the following article:

• TITLE: Synthesis of Branch-Type Cyclophane Tetramers Having a Multivalently Enhanced Guest-Binding Ability

  AUTHORS: Osamu Hayashida, Chihiro Nada, Shuhei Kusano

  KEYWORDS: Cyclophane, Host-Guest Chemistry, Multivalent Effect

  JOURNAL NAME: Advances in Chemical Engineering and Science, Vol.9 No.1, January 23, 2019

  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.