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

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

doi:10.1039/D3DT01320K

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

Zhanjiang Zheng,

*^ab Niyaz Yagafarov,^b Zheng Xu,^a Armelle Ouali,

^c Nobuhiro Takeda,^b Yujia Liu

*^b and Masafumi Unno

*^b

Author affiliations

* Corresponding authors

^a College of Materials, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, Zhejiang, China
E-mail: zzjiang78@hznu.edu.cn

^b Department of Chemistry and Chemical Biology, Graduate School of Science and Technology, Gunma University, 1-5-1 Tenjin-cho, Kiryu 376-8515, Japan
E-mail: unno@gunma-u.ac.jp, yliu@gunma-u.ac.jp

^c ICGM, Univ. Montpellier, CNRS, ENSCM, 1919 route de Mende, Montpellier 34293, Cedex 5, France

Abstract

Tetrachloro- and tetraazide-substituted all-cis-tetraphenylcyclotetrasiloxanes (all-cis-T₄) 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-cis-T₄ 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 K_sv of 8.10 × 10⁴ M⁻¹.

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Article information

DOI: https://doi.org/10.1039/D3DT01320K
Article type: Communication
Submitted: 04 May 2023
Accepted: 03 Jul 2023
First published: 19 Jul 2023

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Dalton Trans., 2023,52, 10298-10304

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

Z. Zheng, N. Yagafarov, Z. Xu, A. Ouali, N. Takeda, Y. Liu and M. Unno, Dalton Trans., 2023, 52, 10298 DOI: 10.1039/D3DT01320K

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Dalton Transactions

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

Abstract

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

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