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Characterization of the thermal and photoinduced reactions of photochromic spiropyrans in aqueous solution

Martin Hammarson (Institutionen för kemi- och bioteknik, Fysikalisk kemi) ; Jesper Nilsson (Institutionen för kemi- och bioteknik, Fysikalisk kemi) ; Shiming Li (Institutionen för kemi- och bioteknik, Fysikalisk kemi) ; Tamas Beke-Somfai (Institutionen för kemi- och bioteknik, Fysikalisk kemi) ; Joakim Andréasson (Institutionen för kemi- och bioteknik, Fysikalisk kemi)
Journal of Physical Chemistry B (1520-6106). Vol. 117 (2013), 43, p. 13561-71.
[Artikel, refereegranskad vetenskaplig]

Six water-soluble spiropyran derivatives have been characterized with respect to the thermal and photoinduced reactions over a broad pH-interval. A comprehensive kinetic model was formulated including the spiro- and the merocyanine isomers, the respective protonated forms, and the hydrolysis products. The experimental studies on the hydrolysis reaction mechanism were supplemented by calculations using quantum mechanical (QM) models employing density functional theory. The results show that (1) the substitution pattern dramatically influences the pKa-values of the protonated forms as well as the rates of the thermal isomerization reactions, (2) water is the nucleophile in the hydrolysis reaction around neutral pH, (3) the phenolate oxygen of the merocyanine form plays a key role in the hydrolysis reaction. Hence, the nonprotonated merocyanine isomer is susceptible to hydrolysis, whereas the corresponding protonated form is stable toward hydrolytic degradation.



Denna post skapades 2013-11-26. Senast ändrad 2015-03-09.
CPL Pubid: 187480

 

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Institutioner (Chalmers)

Institutionen för kemi- och bioteknik, Fysikalisk kemi (2005-2014)

Ämnesområden

Fysikalisk kemi

Chalmers infrastruktur

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Projekt

Denna publikation är ett resultat av följande projekt:


Photochromic systems for solid state molecular electronic devices and light-activated cancer drugs (PHOTOCHROMES) (EC/FP7/203952)