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Synthesis and characterization of gated photochromic diarylethene functionalized with dipicolylamine
Dyes and Pigments ( IF 4.1 ) Pub Date : 2020-01-17 , DOI: 10.1016/j.dyepig.2020.108202
Xiao Guang Hu , Xiao Liang Li , Kwang-Hyun Ahn , Sung Ik Yang

1,2-bis(2-methyl-1-benzothiophene-3-yl)perfluorocyclopentene (BTF6) based photochromic diarylethene functionalized with dipicolylamine (DPA), BTF-DPA has been synthesized, and its photochromic properties have been determined. The photoconversion reaction of o-BTF-DPA was prohibited due to the electronic effect originated from electron donation from DPA to the diarylethene BTF6 framework. The addition of Cu2+ gave rise to dramatically increase the conversion yield of o-BTF-DPA from 0 to 23.86% (for o-BTF-DPA-Cu2+) due to diminishing the electron donation ability of DPA. The addition of EDTA removed Cu2+ from BTF-DPA-Cu2+, which result in suppressing the conversion yield o-BTF-DPA. We also synthesized BTF-DMA and BTF-TMA to examine the mechanism of gated photochromism in diarylethenes. We found that the electron donation ability of DPA plays a critical role in the modulation of photochromic reactivity. The results demonstrated that BTF-DPA could be applicable as a “molecular lock” that requires Cu2+ “key” and EDTA “hand” to unlatch the key. We believe this strategy can be further extended to develop the gated photochromic systems by controlling the electronic state via non-bonding nitrogen-containing ligands.



中文翻译:

二聚烯丙基胺官能化的门控光致变色二芳基乙烯的合成与表征

以二聚烯丙基胺(DPA)官能化的1,2-双(2-甲基-1-苯并噻吩-3-基)全氟环戊烯(BTF6)基光致变色二芳基乙烯,已合成BTF-DPA,并确定了其光致变色性质。的光转化反应ö - BTF-DPA被禁止由于电子效应源于电子给予从DPA到二芳烯BTF6框架。Cu 2+的添加极大地提高了o - BTF-DPA的转化率从0到23.86%(对于o - BTF-DPA-Cu 2+),因为DPA的电子捐赠能力降低。加入EDTA除去的Cu 2+BTF-DPA-Cu系2+,导致抑制转化率ø - BTF-DPA。我们还合成了BTF-DMABTF-TMA,以检查双芳烃中门控光致变色的机理。我们发现,DPA的电子给体能力在光致变色反应性的调节中起关键作用。结果表明,BTF-DPA可以用作需要Cu 2+的“分子锁”“钥匙”和EDTA“手”解锁钥匙。我们认为,通过通过非键合的含氮配体控制电子状态,可以进一步扩展该策略以开发门控光致变色系统。

更新日期:2020-01-17
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