Journal
ACS APPLIED MATERIALS & INTERFACES
Volume 6, Issue 3, Pages 1550-1562Publisher
AMER CHEMICAL SOC
DOI: 10.1021/am404242a
Keywords
fluorescence resonance energy transfer; acidochromism; spirooxazine; spiropyran; Bodipy; photochromism
Funding
- University of Hong Kong
- State Key Laboratory of Supramolecular Structure and Materials, Jilin University
- National Basic Research Program of China (973 Program) [2013CB834701]
- General Research Fund (GRF) [HKU 7051/13P]
- University Grants Committee Areas of Excellence Scheme [AoE/P-03/08]
- University Postdoctoral Fellowship from The University of Hong Kong
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Two series of Bodipy-containing photochromic spirooxazine and spiropyran derivatives have been designed, synthesized and characterized by H-1 NMR, ESI mass spectrometry and elemental analysis. Their electrochemical and photochromic properties were investigated. The photophysical, ultrafast transient absorption, and fluorescence resonance energy transfer (FRET) properties from Bodipy (donor) to the ring-opened merocyanine (acceptor) were also studied. Upon photoexcitation, all the photochromic spirooxazine- and spiropyran-containing compounds exhibited reversible photochromism. Computational studies have been performed to provide further insights into the nature of the electronic transitions for the two classes of compounds. The rate constants and activation parameters for thermal bleaching reactions of compounds SO, SP-alkyne, 1-3, and 8-10 were determined through kinetic studies in acetonitrile. The thermal bleaching reaction rate of the spiropyran-containing compounds is found to be much slower than that of the spirooxazine-containing counterparts.
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