Citation: Yan Zhu, Jia Liu, Meiheng Lv, Tingting Wang, Dongxiang Zhang, Rong Shang, Xin-Dong Jiang, Jianjun Du, Guiling Wang. Heavy-atom-free orthogonal configurative dye 1,7-di-anthra-aza-BODIPY for singlet oxygen generation[J]. Chinese Chemical Letters, ;2024, 35(10): 109446. doi: 10.1016/j.cclet.2023.109446 shu

Heavy-atom-free orthogonal configurative dye 1,7-di-anthra-aza-BODIPY for singlet oxygen generation

Yan Zhu ^{a, 1} ,
Jia Liu ^{b, 1} ,
Meiheng Lv ^a ,
Tingting Wang ^a ,
Dongxiang Zhang ^a ,
Rong Shang ^d ,
Xin-Dong Jiang ^{a, *,} ,
Jianjun Du ^{c, *,} ,
Guiling Wang ^{b, *,}

a.
Liaoning & Shenyang Key Laboratory of Functional Dye and Pigment, Shenyang University of Chemical Technology, Shenyang 110142, China
b.
Department of Cell Biology, China Medical University, Shenyang 110122, China
c.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China
d.
Department of Chemistry, Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 7398526, Japan

xdjiang@syuct.edu.cn

dujj@dlut.edu.cn

glingwang@cmu.edu.cn

Received Date: 7 October 2023
Revised Date: 19 December 2023
Accepted Date: 21 December 2023
Available Online: 22 December 2023

Figures(6)

Spin-orbit, charge-transfer intersystem crossing (SOCT-ISC) can directly overcome the disadvantages of the traditional heavy-atom effect and improve the generation efficiency of reactive oxygen species (ROS). Since orthogonal molecular orbitals of donor-acceptor (D-A) pairs favor the SOCT-ISC transition, herein aza-borondipyrromethenes (aza-BODIPYs) with 1,7-di-anthracyl groups (An-azaBDP) was successfully prepared, owing to steric hindrance to produce a big dihedral angle between the two molecular orbital (MO) planes. Moreover, according to density functional theory (DFT) and time-dependent density functional theory (TDDFT), the energy difference between the S₁-T₁ orbitals of An-azaBDP is small and more inclined towards ISC. An-azaBDP can effectively generate singlet oxygen under light irradiation. An-azaBDP with light irradiation can induce apoptosis in SW620 cells, and can serve as a potential candidate for the treatment of cancer cells and tumors.
- Orthogonal configuration,
- Anthracene,
- Heavy-atom-free,
- Aza-BODIPY,
- Singlet oxygen
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