Switching properties of a spiropyran-cucurbit[7]uril supramolecular assembly: usefulness of the anchor approach.

Abstract

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 host-guest 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.

• Authors: Jesper R Nilsson, Cátia Parente Carvalho, Shiming Li, José Paulo Da Silva, Joakim Andréasson, Uwe Pischel
• Journal: Chemphyschem : a European journal of chemical physics and physical chemistry (Chemphyschem) Vol. 13 Issue 16 Pg. 3691-9 (Nov 12 2012) ISSN: 1439-7641 [Electronic] Germany
• PMID: 22927227 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemical References

• Benzopyrans
• Bridged-Ring Compounds
• Coloring Agents
• Imidazoles
• Indoles
• Nitro Compounds
• cucurbit(7)uril
• merocyanine
• spiropyran

Topics

• Benzopyrans (chemistry)
• Bridged-Ring Compounds (chemistry)
• Coloring Agents (chemistry)
• Hydrolysis
• Imidazoles (chemistry)
• Indoles (chemistry)
• Isomerism
• Light
• Nitro Compounds (chemistry)