Facile Synthesis of Sulfur-Containing Functionalized Disiloxanes with Nonconventional Fluorescence by Thiol–Epoxy Click Reaction

Tang, Jing; Feng, Shengyu; Wang, Dengxu

doi:10.3390/ijms24097785

Open AccessArticle

Facile Synthesis of Sulfur-Containing Functionalized Disiloxanes with Nonconventional Fluorescence by Thiol–Epoxy Click Reaction

by

Jing Tang

^1,2,

Shengyu Feng

² and

Dengxu Wang

^1,2,*

¹

Institute of Novel Semiconductors, State Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, China

²

National Engineering Research Center for Colloidal Materials & Key Laboratory of Special Functional Aggregated Materials, Ministry of Education, Shandong Key Laboratory of Advanced Organosilicon Materials and Technologies, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China

^*

Author to whom correspondence should be addressed.

Int. J. Mol. Sci. 2023, 24(9), 7785; https://doi.org/10.3390/ijms24097785

Submission received: 28 March 2023 / Revised: 22 April 2023 / Accepted: 23 April 2023 / Published: 24 April 2023

(This article belongs to the Special Issue Future Perspectives in Nanostructured Materials Preparation, Characteristics and Applications)

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Abstract

Herein, a series of novel sulfur-containing functionalized disiloxanes based on a low-cost and commercially available material, i.e., 1,3-bis(3-glycidoxypropyl)-1,1,3,3-tetramethyldisiloxane, and various thiol compounds were prepared by thiol–epoxy click reaction. It was found that both lithium hydroxide (LiOH) and tetrabutylammonium fluoride (TBAF) have high catalytic activity after optimizing the reaction condition, and the reaction can be carried out with high yields, excellent regioselectivity, mild reaction condition, and good tolerance of functional groups. These compounds exhibit excellent nonconventional fluorescence due to the formation of coordination bonds between Si atoms and heteroatoms (e.g., S or N) and can emit blue fluorescence upon ultraviolet (UV) irradiation. These results demonstrate that the thiol–epoxy click reaction could promisingly act as an efficient organosilicon synthetic methodology to construct various organosilicon materials with novel structures and functionality, and thus their application scope will be significantly expanded.

Keywords: thiol–epoxy reaction; functionalized disiloxanes; organosilicon synthetic methodology; nonconventional fluorescence

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MDPI and ACS Style

Tang, J.; Feng, S.; Wang, D. Facile Synthesis of Sulfur-Containing Functionalized Disiloxanes with Nonconventional Fluorescence by Thiol–Epoxy Click Reaction. Int. J. Mol. Sci. 2023, 24, 7785. https://doi.org/10.3390/ijms24097785

AMA Style

Tang J, Feng S, Wang D. Facile Synthesis of Sulfur-Containing Functionalized Disiloxanes with Nonconventional Fluorescence by Thiol–Epoxy Click Reaction. International Journal of Molecular Sciences. 2023; 24(9):7785. https://doi.org/10.3390/ijms24097785

Chicago/Turabian Style

Tang, Jing, Shengyu Feng, and Dengxu Wang. 2023. "Facile Synthesis of Sulfur-Containing Functionalized Disiloxanes with Nonconventional Fluorescence by Thiol–Epoxy Click Reaction" International Journal of Molecular Sciences 24, no. 9: 7785. https://doi.org/10.3390/ijms24097785

APA Style

Tang, J., Feng, S., & Wang, D. (2023). Facile Synthesis of Sulfur-Containing Functionalized Disiloxanes with Nonconventional Fluorescence by Thiol–Epoxy Click Reaction. International Journal of Molecular Sciences, 24(9), 7785. https://doi.org/10.3390/ijms24097785

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Facile Synthesis of Sulfur-Containing Functionalized Disiloxanes with Nonconventional Fluorescence by Thiol–Epoxy Click Reaction

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