Origin of Photoluminescence in Organosilicon Compounds Containing Styrene Subunits

Yan, Duanchao; Müller, Thomas; Bolte, Michael; Auner, Norbert

doi:10.1002/9783527619924.ch21

Cited by 2 publications

(1 citation statement)

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“…Arylsilanes are broadly useful compounds in material science, biochemical and pharmacological research, as well as organic synthesis. [ 1‐5 ] Therefore, the development of an efficient strategy to incorporate silicon motifs into organic molecules by forming C(aryl)—Si bonds is of great interest and much importance. Among possible approaches, the catalytic coupling reactions of silicon electrophiles represent a valuable strategy to construct C(aryl)—Si bonds, [ 6‐21 ] because silicon electrophiles like chlorosilanes [ 22‐25 ] are much more abundant and cheaper starting materials than silicon organometallic reagents [ 26‐30 ] and hydrosilanes.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Iron‐Catalyzed Reductive C(aryl)—Si Cross‐Coupling of Diaryl Ethers with Chlorosilanes

Liu,

Wu,

Cong

et al. 2023

Chin. J. Chem.

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Comprehensive SummaryThe reductive cross‐coupling between C(aryl)–O and Si–Cl bonds is of much importance as a valuable strategy for the construction of C(aryl)–Si bonds but has remained a great challenge. Here we report a reductive cross‐coupling of diaryl ethers and chlorosilanes via strong electrophilic C(aryl)–O and Si–Cl bonds cleavage by iron catalysis, which constitutes an efficient protocol for the synthesis of a range of functionalized arylsilanes. The combination of low cost FeCl2 as the precatalyst and iPrMgCl as the reductant shows high activity in the successive cleavage of unactivated C(aryl)–O bonds of diaryl ethers and strong electrophilic Si–Cl bonds of chlorosilanes, allowing their cross‐coupling in a reductive fashion. The low‐valent iron species generated in situ by reduction of FeCl2 with iPrMgCl was proposed, which prefers to initially cleavage the C(aryl)–O bond of diaryl ethers with the chelation help of an o‐amide auxiliary.This article is protected by copyright. All rights reserved.

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Section: Background and Originality Contentmentioning

confidence: 99%

Iron‐Catalyzed Reductive C(aryl)—Si Cross‐Coupling of Diaryl Ethers with Chlorosilanes

Liu,

Wu,

Cong

et al. 2023

Chin. J. Chem.

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Molecular Optical Switches: Synthesis, Structure, and Photoluminescence of Spirosila Compounds

Yan

Mohsseni‐Ala

Auner

et al. 2007

Chemistry A European J

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Starting from a silicon dichloro substituted silole and a silacyclobutene, a series of new organosilicon-based spiro compounds was synthesized by using standard organometallic reaction procedures. The spiro compounds that combine two organic photoactive subunits at one silicon center were fully characterized by the usual analytical and spectroscopic methods, which include molecular structure determination by single-crystal X-ray analysis. Photoluminescence spectra of the compounds were recorded in the solid state and also as dilute solutions in THF. Interpretation of the spectra revealed that photoluminescence in this series of compounds originated from the stilbene or its vinylogue subunits. Different linkages of these groups to the silicon atoms (cyclic or open structures, four- or five-membered cycles) strongly affected both the excitation and the emission spectra, which show different emission maxima depending on the state of the sample (solid state or in solution) and the wavelength of light used for excitation. Thus, owing to their optoelectronic properties these compounds might be useful tools for the design of sensitive sensor materials and of optical switches.

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Origin of Photoluminescence in Organosilicon Compounds Containing Styrene Subunits

Cited by 2 publications

References 6 publications

Iron‐Catalyzed Reductive C(aryl)—Si Cross‐Coupling of Diaryl Ethers with Chlorosilanes

Iron‐Catalyzed Reductive C(aryl)—Si Cross‐Coupling of Diaryl Ethers with Chlorosilanes

Molecular Optical Switches: Synthesis, Structure, and Photoluminescence of Spirosila Compounds

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