Water-soluble macrocyclic paddlanes and propellane as a new class of host molecules

Tobe Yoshito*, Hisashi Fujita, Itsuyo Wakaki, Kaoru Terashima, Kazuya Kobiro, Kiyomi Kakiuchi, Yoshinobu Odaira

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations


A new class of water-soluble macrocyclic polyamine host molecules containing bicyclo[2.2.2]octane or bicyclo[4.4.0]decane subcyclic units, tetra-azabispaddlane (2a), hexa-azatrispaddlane (3a), and tetra-azabispropellane (4a), have been synthesized. While trispaddlane (3a) and bispropellane (4a) showed only line broadening of the n.m.r. spectra at -59 °C, bispaddlane (2a) exhibited coalescence behaviour at -31 °C, (benzyl protons), -35 °C (N-methylene protons adjacent to the bicyclo-octane unit), and -50 °C (ArH). The association constants of (2a)-(4a) and the fluorescent hydrophobic guest, 1-anilinonaphthalene-8-sulphonate, were determined in KCl-HCl buffer of pH 1.68 to be 2.7 × 102 M-1, 1.1 × 10 3 M-1, and 2.2 × 102 M-1, respectively.

Original languageEnglish
Pages (from-to)2681-2684
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
StatePublished - 1 Dec 1984

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