Optical control over Pb2+ binding to a crown ether-containing chromene

Stauffer, Mark T.; Knowles, David B.; Brennan, Carrie; Funderburk, Lance H.; Lin, Fu-Tyan; Weber, Stephen G.

doi:10.1039/a607141d

Cited by 40 publications

(17 citation statements)

References 6 publications

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“…To the best of our knowledge, however, there has been only one report on chromene derivatives bearing a crown ether moiety. [13] In a continuation of our previous work dealing with crowned spirobenzopryran [14,15] and spirooxazine, [16] in this paper we report chromene derivatives bearing a monoazacrown ether moiety, namely crowned chromenes.…”

Section: Scheme 1 Photoisomerization Of Chromenementioning

confidence: 92%

Synthesis and Photochromism of Novel Chromene Derivatives Bearing a Monoazacrown Ether Moiety

et al. 2003

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Crowned chromenes − four novel naphthopyrans (chromenes) bearing monoaza-12-crown-4, -15-crown-5, -18-crown-6, and a noncyclic analogue at the 5-position − were synthesized, and their photochromism in acetonitrile was examined in the presence of alkali and alkaline-earth metal ions. Incorporation of crown ether units to chromene moieties facilitated to a great extent both the thermal isomerization and photoisomerization of the chromene moiety, reflecting the metal-ion-binding ability of the crown ether moiety. Comparison of the crowned chromenes with the cor-

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Section: Scheme 1 Photoisomerization Of Chromenementioning

confidence: 92%

Synthesis and Photochromism of Novel Chromene Derivatives Bearing a Monoazacrown Ether Moiety

et al. 2003

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“…47 The electron density of the crown ether ring fused to one of the two phenyl groups of its isomer 25a can be reduced by photoinduced ring opening by UV irradiation. The carbocation of the open form is consequently stabilized by electron donation from the crown ether.…”

Section: Photoswitchable Receptors Based On Chromenesmentioning

confidence: 99%

Molecular switches as photocontrollable “smart” receptors

2012

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This critical review focuses on the development of photochromic compounds as sensors for cations, anions, and biologically important molecules. The review commences with a brief description of photochromism and the strategies to exploit photochromic molecular switches' properties for sensing application. This is followed by a summary of photoswitchable receptors emerged to date and classified according to the photochromic structure they are based on. These include azobenzenes, fulgides, dithienylethenes, dihydroindolizines, chromenes and spiropyrans.

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“…Photochromic compounds have been used to control protein and enzyme activity (1–12) and metal‐ion binding (13–31). In metal‐ion binding systems, light can be used to drive photochromic molecules from one stable or metastable avid binding structure to another stable or metastable loosely binding structure.…”

Section: Introductionmentioning

confidence: 99%

Kinetic Analysis of a Photosensitive Chelator and its Complex with Zn(II)¶

Stephens

Geary

Weber

2007

Photochemistry and Photobiology

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The reversible sequestration and release of metal ions is an important objective in biological and environmental research. Unfortunately, although there have been dramatic examples of metal ion activity control, there are very few quantitative investigations of stoichiometry, equilibria and kinetics. A significant contributor to this lack of quantitative work is the complexity of many photochromic systems. Therefore, we have attempted to create a simple, reversible photochromic metal‐ion chelator that can be analyzed quantitatively. The chelator should have certain other attributes as well, namely, that it binds to divalent metal ions (because of their extreme biological importance) and that it binds metal ions in the dark so that light is used to release metal ions rather than sequester them. The photochromic chelator (1) binds to divalent metal ions [Zn(II), Cu(II), Pb(II), Hg(II), Fe(II), Co(II) and Cd(II); other metal ions have not yet been tested] in the dark with a significant binding strength. In both methanol (by spectrophotometry) and methanol–water (by voltammetry), the stoichiometry of the 1–Zn(II) complex is 2:1. The binding constant (K1K2) is on the order of 1012–1014M−2 in methanol and 5.0 × 108M−2 in 50% aqueous methanol. The chelator 1 is photolabile, yielding 2 with a quantum efficiency of 0.91. In a solution containing excess Zn(II), so that over 99% of the ligand exists as the monodentate complex, photolysis produces 2 with a quantum efficiency of 0.15. A kinetic analysis leads to the conclusion that the complex itself is photolabile.

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Optical control over Pb2+ binding to a crown ether-containing chromene

Cited by 40 publications

References 6 publications

Synthesis and Photochromism of Novel Chromene Derivatives Bearing a Monoazacrown Ether Moiety

Synthesis and Photochromism of Novel Chromene Derivatives Bearing a Monoazacrown Ether Moiety

Molecular switches as photocontrollable “smart” receptors

Kinetic Analysis of a Photosensitive Chelator and its Complex with Zn(II)¶

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