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水溶性手性四嗪衍生物:从高激发态的圆偏振发光到光动力疗法的应用

Water-soluble chiral tetrazine derivatives: towards the application of circularly polarized luminescence from upper-excited states to photodynamic therapy.

作者信息

He Tingchao, Ren Can, Luo Yu, Wang Qi, Li Junzi, Lin Xiaodong, Ye Chuanxiang, Hu Wenbo, Zhang Junmin

机构信息

College of Physics and Energy , Shenzhen University , Shenzhen 518060 , China.

College of Chemistry and Environmental Engineering , Shenzhen University , Shenzhen 518060 , China . Email:

出版信息

Chem Sci. 2019 Mar 8;10(15):4163-4168. doi: 10.1039/c9sc00264b. eCollection 2019 Apr 21.

DOI:10.1039/c9sc00264b
PMID:31057744
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6471655/
Abstract

A new family of water-soluble chiral tetrazine derivatives and is reported. Spectroscopic studies reveal that the derivatives violate Kasha's rule and emit from their upper-excited states (S , > 1). The transition assignments are supported by time-dependent density functional theory calculations. More importantly, both chromophores exhibit anisotropy factors on the order of ∼10 to 10 for circular dichroism and circularly polarized luminescence (CPL) from upper-excited states. Additionally, the nonplanar geometry of the derivatives induces a significant yield of triplet excited states. Transient absorption spectroscopic measurements reveal high triplet quantum yields of ∼86% for and ∼81% for . Through studies, we demonstrate that the derivatives can be used as photodynamic therapy (PDT) agents, providing a highly efficient form of cancer therapy. This study is the first demonstration of simple organic molecules with CPL from upper-excited states and efficient PDT.

摘要

报道了一类新的水溶性手性四嗪衍生物。光谱研究表明,这些衍生物违反了卡沙规则,从其较高激发态(S ,>1)发射。跃迁归属得到了含时密度泛函理论计算的支持。更重要的是,两种发色团对于来自较高激发态的圆二色性和圆偏振发光(CPL)都表现出约10到10量级的各向异性因子。此外,衍生物的非平面几何结构诱导出显著产率的三重激发态。瞬态吸收光谱测量表明,对于 ,三重态量子产率高达约86%,对于 约为81%。通过 研究,我们证明这些衍生物可用作光动力疗法(PDT)药物,提供一种高效的癌症治疗形式。这项研究首次证明了具有来自较高激发态的CPL和高效PDT的简单有机分子。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2f4/6471655/0a53205584d6/c9sc00264b-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2f4/6471655/02509bf50f83/c9sc00264b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2f4/6471655/079c9922c576/c9sc00264b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2f4/6471655/e57338888159/c9sc00264b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2f4/6471655/625cd02dfcc5/c9sc00264b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2f4/6471655/b2387e5d1309/c9sc00264b-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2f4/6471655/0a53205584d6/c9sc00264b-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2f4/6471655/02509bf50f83/c9sc00264b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2f4/6471655/079c9922c576/c9sc00264b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2f4/6471655/e57338888159/c9sc00264b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2f4/6471655/625cd02dfcc5/c9sc00264b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2f4/6471655/b2387e5d1309/c9sc00264b-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2f4/6471655/0a53205584d6/c9sc00264b-f5.jpg

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