Organo-functionalized trimethoxysilanes featuring thioester linkage: Synthetic and UV–Vis spectral investigations

• A new pathway for the synthesis of alkoxysilanes is developed.
• The silanes are meticulously characterized by IR and NMR spectroscopic techniques.
• The substituent effect on the absorption behaviour is analysed.
• The solvatochromic behaviour is studied by utilizing Kamlet Taft approach.

The current work reveals a series of new organo-functionalized trimethoxysilanes (OfTMS) linked via a 3C tether to the thioester group along with the inclusion of versatile aromatic and heteroaromatic sequences. The synthetic procedure implicates the one-pot thioesterification reaction of the precursor carboxylic acids (1a-r) with 3-mercaptopropyltrimethoxysilane (MPTMS), stimulated by 1,1′-carbonyldiimidazole (CDI). The OfTMS have been attentively characterized by elemental analysis, infrared and [1H, 13C] NMR spectroscopic techniques. The UV–Vis absorption behaviour demonstrates that the alkoxysilanes possess high sensitivity to the changes caused in the environment on account of different substitutions. Furthermore, the solvent effect on the absorption spectra has been scrutinized and quantified using the Kamlet-Taft approach. Importantly, the fabricated stable alkoxysilanes can be aspired for advance applications in the field of material science.

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