Synthesis, Characterization, and Photophysical Properties of Bodipy-Spirooxazine and -Spiropyran Conjugates: Modulation of Fluorescence Resonance Energy Transfer Behavior via Acidochromic and Photochromic Switching
Synthesis, Characterization, and Photophysical Properties of Bodipy-Spirooxazine and -Spiropyran Conjugates: Modulation of Fluorescence Resonance Energy Transfer Behavior via Acidochromic and Photochromic Switching
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DOI：
10.1021/am404242a
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发表时间：
2014-02-12
影响因子：
9.5
通讯作者：
Yam, Vivian Wing-Wah
中科院分区：
文献类型：
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作者：
Kong, Lingcan;Wong, Hok-Lai;Yam, Vivian Wing-Wah
设计、合成了两个系列的含Bodipy的光致变色螺恶嗪和螺吡喃衍生物，并通过H-1 NMR、ESI质谱和元素分析进行了表征。研究了它们的电化学和光致变色性能。还研究了从 Bodipy（供体）到开环部花青（受体）的光物理、超快瞬态吸收和荧光共振能量转移（FRET）特性。在光激发后，所有光致变色的含螺恶嗪和螺吡喃的化合物均表现出可逆的光致变色性。已经进行了计算研究，以进一步了解这两类化合物的电子跃迁的性质。通过乙腈中的动力学研究确定了化合物 SO、SP-alkyne、1-3 和 8-10 的热漂白反应的速率常数和活化参数。发现含螺吡喃化合物的热漂白反应速率比含螺恶嗪对应物的热漂白反应速率慢得多。
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.