Switching Properties of a Spiropyran-Cucurbit [7] uril Supramolecular Assembly: Usefulness of the Anchor Approach
Artikel i vetenskaplig tidskrift, 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

Författare

Jesper Nilsson

Chalmers, Kemi- och bioteknik, Fysikalisk kemi

C. P. Carvalho

Universidad de Huelva

Shiming Li

Chalmers, Kemi- och bioteknik, Fysikalisk kemi

J. P. Da Silva

Universidade do Algarve

Joakim Andreasson

Chalmers, Kemi- och bioteknik, Fysikalisk kemi

U. Pischel

Universidad de Huelva

ChemPhysChem

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

Vol. 13 3691-3699

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

Europeiska kommissionen (FP7), 2008-09-01 -- 2013-08-31.

Fotoswitchning av molekylära egenskaper baserade på fotokroma reaktioner

Vetenskapsrådet (VR), 2011-01-01 -- 2016-12-31.

Ämneskategorier

Kemi

DOI

10.1002/cphc.201200468