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Photochromism of a Merocyanine Dye Bound to Sulfonatocalixarenes: Effect of pH and the Size of Macrocycle on the Kinetics

Photochromism of a Merocyanine Dye Bound to Sulfonatocalixarenes: Effect of pH and the Size of Macrocycle on the Kinetics

Zsombor Miskolczy, László Biczók

J Phys Chem B. 2013 Jan 17;117(2):648-53.

PMID: 23289744

Abstract:

The effect of 1:1 complex formation on the photochromic behavior of the merocyanine isomer of a nitro-substituted spirobenzopyran dye was studied in aqueous solution using 4-sulfonatocalixarene (SCXn) cavitands possessing four or eight phenol units. The binding constants were independent of the size of the macrocycle, and about 7-fold more stable associates were produced at pH 2.3 than in slightly alkaline solution. The complexation with SCXn diminished the acidity of protonated merocyanine (trans-MCH(+)) and precluded its photoinitiated transition to spirobenzopyran form, but did not affect the reactions in basic media. Upon exposure to light, the complexed trans-MCH(+) was converted to cis isomer. The association with 4-sulfonatocalix[4]arene slowed down the thermal back reaction in the dark to a larger extent than the confinement to 4-sulfonatocalix[8]arene. Both the activation energy and the Arrhenius A factor were significantly larger when the smaller, more rigid macrocycle served as a host.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS77389	Merocyanine dye, HB194			Price

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