Proton-Stabilized Photochemically Reversible E/ Z Isomerization of Spiropyrans

The Journal of Physical Chemistry. B
L KortekaasWesley R Browne

Abstract

Spiropyrans undergo Cspiro-O bond breaking to their ring-open protonated E-merocyanine form upon protonation and irradiation via an intermediate protonated Z-merocyanine isomer. We show that the extent of acid-induced ring opening is controlled by matching both the concentration and strength of the acid used and with strong acids full ring opening to the Z-merocyanine isomer occurs spontaneously allowing its characterization by 1H NMR spectroscopy as well as UV/vis spectroscopy, and reversible switching between Z/ E-isomerization by irradiation with UV and visible light. Under sufficiently acidic conditions, both E- and Z-isomers are thermally stable. Judicious choice of acid such that its p Ka lies between that of the E- and Z-merocyanine forms enables thermally stable switching between spiropyran and E-merocyanine forms and hence pH gating between thermally irreversible and reversible photochromic switching.

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Citations

Aug 21, 2018·Physical Chemistry Chemical Physics : PCCP·Parth K PatelKarin Y Chumbimuni-Torres
Jun 1, 2019·Chemical Society Reviews·Luuk Kortekaas, Wesley R Browne
Jun 25, 2019·Chemistry, an Asian Journal·Danyang LiuSean Xiao-An Zhang
Nov 21, 2020·Angewandte Chemie·Christina M GeiselhartChristopher Barner-Kowollik
Apr 17, 2021·The Journal of Physical Chemistry. a·Jorn D SteenWesley R Browne
Jun 1, 2021·ACS Applied Materials & Interfaces·Sara SantiagoGonzalo Guirado
May 1, 2021·Chemistry : a European Journal·Christoph KaiserJosef Wachtveitl
Jun 15, 2021·Chemical Science·Cesare BertonCristian Pezzato
Jun 8, 2021·Chemistry : a European Journal·Pedro FerreiraPablo Ballester
Jul 22, 2020·The Journal of Physical Chemistry. a·Luuk KortekaasWesley R Browne
Mar 19, 2020·The Journal of Physical Chemistry. a·Ya-Hui ZhangGanglong Cui
Oct 20, 2018·Journal of the American Chemical Society·Cassandra L FlemingJoakim Andréasson
Oct 1, 2021·Chemical Society Reviews·Jana VolarićBen L Feringa
Dec 1, 2021·Journal of the American Chemical Society·Laura WimbergerJonathon E Beves

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Methods Mentioned

BETA
NMR

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