A Dynamic and Responsive Host in Action: Light-Controlled Molecular Encapsulation

Seán T J Ryan; Jesús Del Barrio; Reynier Suardíaz; Daniel F Ryan; Edina Rosta; Oren A Scherman

doi:10.1002/anie.201607693

A Dynamic and Responsive Host in Action: Light-Controlled Molecular Encapsulation

Angew Chem Int Ed Engl. 2016 Dec 23;55(52):16096-16100. doi: 10.1002/anie.201607693. Epub 2016 Oct 28.

Authors

Seán T J Ryan¹, Jesús Del Barrio^{2

1}, Reynier Suardíaz³, Daniel F Ryan⁴, Edina Rosta³, Oren A Scherman¹

Affiliations

¹ Melville Laboratory for Polymer Synthesis, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
² Schlumberger Gould Research, Madingley Road, Cambridge, CB3 0EL, UK.
³ Department of Chemistry, King's College London, London, SE1 1DB, UK.
⁴ NASA Goddard Space Flight Center, Greenbelt, MD, USA.

Abstract

The rational design of a flexible molecular box, oAzoBox⁴⁺ , incoporating both photochromic and supramolecular recognition motifs is described. We exploit the E↔Z photoisomerization properties of azobenzenes to alter the shape of the cavity of the macrocycle upon absorption of light. Imidazolium motifs are used as hydrogen-bonding donor components, allowing for sequestration of small molecule guests in acetonitrile. Upon E→Z photoisomerization of oAzoBox⁴⁺ the guest is expelled from the macrocyclic cavity.

Keywords: host-guest systems; hydrogen bonds; macrocycles; photochemistry; supramolecular chemistry.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't