含联萘酚和三唑的Janus环以及29至8至29元三环梯型杂化硅氧烷：在阴离子荧光传感中的应用。

BINOL and triazole-containing Janus rings and 29-8-29-membered tricyclic ladder-type hybridized siloxane: application in the fluorescence sensing of anions.

作者信息

Zheng Zhanjiang, Yagafarov Niyaz, Xu Zheng, Ouali Armelle, Takeda Nobuhiro, Liu Yujia, Unno Masafumi

机构信息

College of Materials, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, 311121, Zhejiang, China.

Department of Chemistry and Chemical Biology, Graduate School of Science and Technology, Gunma University, 1-5-1 Tenjin-cho, Kiryu 376-8515, Japan.

出版信息

Dalton Trans. 2023 Aug 1;52(30):10298-10304. doi: 10.1039/d3dt01320k.

DOI:10.1039/d3dt01320k

PMID:37466385

Abstract

Tetrachloro- and tetraazide-substituted all--tetraphenylcyclotetrasiloxanes (all--T) 2 and 3 were synthesized in high yields and were fully characterized. Then the precursor 3 underwent CuAAC click reaction with monopropargyl BINOL 4 and dipropargyl BINOL 6 to give the novel BINOL and triazole-containing all--T cyclic siloxane 5 and the 29-8-29-membered-ring ladder-type hybrid siloxane 7. The sensing ability of compounds 5 and 7 towards anions was studied as well, and it was observed that 7 could selectively recognize iodides through synergistic C-H⋯I hydrogen bonding, resulting in an impressive fluorescence quenching with a of 8.10 × 10 M.

摘要

四氯和四叠氮基取代的全 - 四苯基环四硅氧烷（全 - T）2和3以高产率合成并得到充分表征。然后前体3与单炔丙基联萘酚4和二炔丙基联萘酚6进行铜催化的叠氮化物 - 炔烃环加成（CuAAC）点击反应，得到新型含联萘酚和三唑的全 - T环硅氧烷5以及29 - 8 - 29元环梯型杂化硅氧烷7。还研究了化合物5和7对阴离子的传感能力，观察到7可以通过协同的C - H⋯I氢键选择性识别碘化物，导致令人印象深刻的荧光猝灭，猝灭常数为8.10×10 M。