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Study of the self-association of molecular tweezers bearing two different arms: influence of the stereoelectronic effects of the arm substituents

  • Béatrice LegouinEmail author
  • Arnaud Bondon
  • Clément Orione
  • Solenn Ferron
  • Philippe Uriac
Original Article
  • 14 Downloads

Abstract

In the general field of molecular recognition, the self-assembly of a tweezer bearing a R(+) usnic acid arm and a substituted 1,8-naphthalimide moiety as a second arm was investigated through a 1H NMR study. Two self-association modes were evidenced: either the usnic acid arms (mode A) or the naphthalimide ones (mode B) were face to face in the center of the dimer. The existence of a third non-symmetrical mode (mode C) has not been evidenced experimentally. The behavior of these tweezers was discussed taking into account the electronic density of the naphtalimide arms and the slow mode A/mode B exchange rate (EXSY experiments). Only the mode A was observed when naphthalimide was either non-substituted (1) or substituted by Br (2). With one or two electrodonating substituents (OCH3 (3) or (OCH3)2 (4) or N(CH3)2 (5)) both modes A and B occured in a 50/50 ratio. This ratio depended on temperature for tweezer 3.

Keywords

Tweezer Self-association Supramolecular recognition 1H NMR 

Notes

Acknowledgements

The authors Pr D. Jacquemin and Dr J. Graton (CEISAM, Nantes, France) for fruitful discussions, Dr P. Jéhan (SCANMAT, Rennes, France) for mass spectrometry and Dr N. Levoin (Bioprojet-Biotech, France) for charge calculations. We are most grateful to the PRISM core facility (Rennes-Angers, France) for NMR spectrometer access.

Supplementary material

10847_2019_954_MOESM1_ESM.docx (5.7 mb)
Supplementary material 1 (DOCX 5811 kb)

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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Univ Rennes, CNRS, ISCR– UMR 6226RennesFrance
  2. 2.SCANMATRennesFrance

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