Switching Properties of a Spiropyran-Cucurbit [7] uril Supramolecular Assembly: Usefulness of the Anchor Approach
Journal article, 2012

A nitrospiropyran, which was modified with a cadaverine-derived anchor, was investigated with respect to its thermally induced isomerizations, hydrolytic stability of the merocyanine form, and photochromic ring closure. The hostguest complexation of the anchor by the cucurbit[7]uril macrocycle, evidenced by absorption titration, NMR spectroscopy, and electrospray ionization mass spectrometry, produced significant improvements of the switching properties of the photochrome: 1) appearance of the merocyanine form about 70 times faster, 2) practically unlimited hydrolytic stability of the merocyanine (two and a half days without any measureable decay), and 3) fast, clean, and fatigue-resistant photoinduced ring closure back to the spiro form. The importance of an adequate molecular design of the anchor was demonstrated by including control experiments with spiropyrans with a shorter linker or without such structural asset.

hydrolysis

complexes

lock-in detection

pk(a)

drug-delivery

energy-transfer

acidochromism

shifts

photochromism

cucurbiturils

photoswitchable nanoparticles

molecular switches

cucurbiturils

aqueous-solution

fluorescent dye

host-guest chemistry

Author

Jesper Nilsson

Chalmers, Chemical and Biological Engineering, Physical Chemistry

C. P. Carvalho

University of Huelva

Shiming Li

Chalmers, Chemical and Biological Engineering, Physical Chemistry

J. P. Da Silva

University of Algarve

Joakim Andreasson

Chalmers, Chemical and Biological Engineering, Physical Chemistry

U. Pischel

University of Huelva

ChemPhysChem

1439-4235 (ISSN) 1439-7641 (eISSN)

Vol. 13 16 3691-3699

Photochromic Systems for Solid State Molecular Electronic Devices and Light-Activated Cancer Drugs (PHOTOCHROMES)

European Commission (FP7), 2008-09-01 -- 2013-08-31.

Photonic switching of molecular properties using photochromes

Swedish Research Council (VR), 2011-01-01 -- 2016-12-31.

Subject Categories

Chemical Sciences

DOI

10.1002/cphc.201200468

More information

Created

10/8/2017