Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (9): 3666-3675.DOI: 10.6023/cjoc202604049 Previous Articles     Next Articles

ARTICLE

基于n→π*相互作用调控偶氮苯光开关顺式异构体的热稳定性

石可添, 韦相宇, 海宇*(), 刘丽娟, 占田广, 章康达*()   

  1. 浙江师范大学化学与材料科学学院 先进催化材料教育部重点实验室全省先进催化与吸附材料重点实验室 浙江金华 321004
  • 收稿日期:2026-04-29 修回日期:2026-06-26 发布日期:2026-07-23
  • 通讯作者: 海宇, 章康达
  • 基金资助:
    国家自然科学基金(22271255); 浙江省自然科学基金(LR22B020001); 浙江省自然科学基金(LQ24B020007)

Modulating the Thermal Stability of cis Isomers of Azobenzene Photoswitches via n→π* Interactions

Ketian Shi, Xiangyu Wei, Yu Hai*(), Lijuan Liu, Tianguang Zhan, Kangda Zhang*()   

  1. Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Zhejiang Key Laboratory of Advanced Catalysis and Adsorption Materials, College of Chemistry and Materials Science, Zhejiang Normal University, Jinhua, Zhejiang 321004
  • Received:2026-04-29 Revised:2026-06-26 Published:2026-07-23
  • Contact: Yu Hai, Kangda Zhang
  • About author:

    Dedicated to the 100th anniversary of the birth of Professor Xikui Jiang.

  • Supported by:
    National Natural Science Foundation of China(22271255); Natural Science Foundation of Zhejiang Province(LR22B020001); Natural Science Foundation of Zhejiang Province(LQ24B020007)

Azobenzenes are a class of important molecular photoswitches with wide-ranging applications in energy storage, supramolecular assembly, biomedicine and beyond. However, it remains a significant challenge to effectively tune the thermal stability of their cis-isomers without compromising the key photoswitching properties such as absorption wavelength and isomerization efficiency. In this research, a unique n→π* interaction based noncovalent strategy is deccribed for tuning the cis-isomer thermal stability of azobenzene photoswitches, for which a series of azo molecules were designed and synthesized by introducing a methoxy group (providing n electron) and different carbonyl units (providing π* orbital) at the meta-positions of azo double bond, respectively. The UV-Vis and 1H NMR experiments revealed that these photoswitches could undergo reversible E⇄Z photoisomerization upon 365 nm UV and 430 nm visible light irradiation. The FT-IR spectra verified the existence of n→π* interactions in the cis-isomers, which could be enhanced by reducing the electron-withdrawing nature of the carbonyl units or increasing the solvent polarity, thereby improving the thermal stability of the photoswitches. These findings provide new insights for the design of new molecular photoswitches with tunable thermal stability.

Key words: photoswitches, azobenzene, n→π* interaction, thermal stability