Inclusion complexes between amphiphilic phenyleneethynylene fluorophores and cyclodextrins in aqueous media

Journal article

Authors/Editors

NAKORN NIAMNONT

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Publication Details

Author list: Siripornnoppakhun W., Niamnont N., Krumsri A., Tumcharern G., Vilaivan T., Rashatasakhon P., Thayumanavan S., Sukwattanasinitt M.

Publisher: American Chemical Society

Publication year: 2012

Journal: Journal of Physical Chemistry B (Soft Condensed Matter and Biophysical Chemistry) (1520-6106)

Volume number: 116

Issue number: 40

Start page: 12268

End page: 12274

Number of pages: 7

ISSN: 1520-6106

eISSN: 1520-5207

URL: https://www.scopus.com/inward/record.uri?eid=2-s2.0-84868149424&doi=10.1021%2fjp3057652&partnerID=40&md5=0d727a060ce07a10ffa92c3f3ada904b

Languages: English-Great Britain (EN-GB)

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Abstract

Binding events of cyclodextrins (CyD's) in aqueous media are important for designing and explaining the host-guest chemistry applied in sensing and controlled release systems. A water-soluble tricationic compound (3N +) with three branches of phenyleneethynylene fluorescent moieties and its related amphiphilic compounds (3C-, N0N+, N +, and 2N+) are employed as molecular probes in the systematic characterization of the supramolecular interactions with CyD's (α, β, and γ). The strong fluorescence enhancement, combined with induced circular dichroism (CD) signals and 1H NMR data, is evidence of 1:1 static inclusion complexes of 3N+/γ-CyD and 2N +/γ-CyD. 3N+ presents a structural design which can form inclusion complexation with γ-CyD with one of the highest binding constants of 3.0 × 104. The relatively moderate fluorescence enhancement, shift of 1H NMR signals, and weak induced CD signals indicate fast exchange complexation of β-CyD with the amphiphilic guest molecules. The interaction with α-CyD is perceived only for N0N+, the only nonbranched fluorescent guest model, via its strong fluorescence enhancement. However, the lack of 1H NMR signal splitting and the lack of induced CD signals suggest the noninclusion mode of binding between N0N+ and α-CyD. © 2012 American Chemical Society.

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