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.
photochromism
host-guest chemistry
aqueous-solution
hydrolysis
acidochromism
energy-transfer
drug-delivery
fluorescent dye
photoswitchable nanoparticles
shifts
cucurbiturils
lock-in detection
cucurbiturils
molecular switches
pk(a)
complexes
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 16 3691-3699Fotoswitchning av molekylära egenskaper baserade på fotokroma reaktioner
Vetenskapsrådet (VR) (2010-280), 2011-01-01 -- 2016-12-31.
Photochromic Systems for Solid State Molecular Electronic Devices and Light-Activated Cancer Drugs (PHOTOCHROMES)
Europeiska kommissionen (EU) (EC/FP7/203952), 2008-09-01 -- 2013-08-31.
Ämneskategorier
Kemi
DOI
10.1002/cphc.201200468