Shanghai Key Laboratory of Electrical Insulation and Thermal Aging, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China.
School of Chemical Science and Engineering, Tongji University, Shanghai, 200092, P. R. China.
Chemistry. 2019 Oct 17;25(58):13402-13410. doi: 10.1002/chem.201902897. Epub 2019 Sep 13.
Molecular photoswitches (e.g., azobenzenes) can reversibly interconvert between their thermodynamically stable and metastable isomers upon light irradiations. However, it remains challenging to integrate both high bidirectional photoconversion and long metastable-state lifetime into a photoswitchable functionality. Here, we introduce pyrazolylazophenyl ethers (pzAzo ethers) as a class of azo photoswitches that provides quantitative (>98 %) trans-cis photoisomerization (365 nm light), near-quantitative (95-96 %) reverse isomerization (532 nm light), and a long cis-isomer half-life of three months. They can be easily synthesized in high yields and readily functionalized at one or both sides with a broad scope of substituent groups. Molecular systems incorporating pzAzo ethers can be endowed with high responsiveness, robust reversibility, and long persistent metastable states. Such superior yet pragmatic azo switches hold high promise for upgraded photoregulation in many light-responsive applications.
分子光开关（例如偶氮苯）可以在光照下可逆地在热力学稳定和亚稳异构体之间相互转换。然而，将高双向光转化和长亚稳态寿命集成到光开关功能中仍然具有挑战性。在这里，我们引入吡唑基偶氮苯基醚（pzAzo 醚）作为一类偶氮光开关，它提供定量（>98%）的反式-顺式光异构化（365nm 光）、近乎定量（95-96%）的反向异构化（532nm 光）和三个月的长顺式异构体半衰期。它们可以高产率地轻松合成，并可以在一侧或两侧进行广泛的取代基官能化。包含 pzAzo 醚的分子系统可以具有高响应性、强可逆性和长持久亚稳态。这种优越而实用的偶氮开关有望在许多光响应应用中升级光调控。
