Synthesis and characterization of functionalized molecular and macromolecular double-decker silsesquioxane systems

Żak, Patrycja; Majchrzak, Mariusz; Wilkowski, Grzegorz; Dudziec, Beata; Dutkiewicz, Michał; Marciniec, Bogdan

doi:10.1039/c5ra20848c

Cited by 35 publications

(9 citation statements)

References 35 publications

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“…At the same time, chemists are looking for synthetic routes exploiting among others hydrosilylation reaction to obtain novel, functionalized Si-based reagents with a specific structure such as silsesquioxanes. [17][18][19][20][21][22][23][24][25][26][27] While hydrosilylation of olefins with silanes has been widely studied, [3,28] the reports on T 8 silsesquioxanes are limited [5,6,[29][30][31][32][33][34] and for double-decker systems of both closed (D 2 T 8 [4,19,25,[35][36][37] ) and opened (M 4 T 8 [38][39][40][41][42][43] ) structure even more scant. [5] Cage-like derivatives have driven much attention due to specific physicochemical properties (governed by the nature of their silicate rigid core and by the number and type of functional groups attached to it) affecting directions of their broad applications from material chemistry to medicine.…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Route for the Synthesis of a Novel Generation of Tetraorganofunctional Double‐decker Type of Silsesquioxanes

et al. 2019

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We present an efficient methodology for the synthesis of tetrafunctionalized double-decker silsesquioxanes via hydrosilylation reaction. An investigation of the catalytic system, olefin structure, chemical and steric surrounding of SiÀ H moiety in the respective reagent was carried out on the progress, selectivity and rate of hydrosilylation process. Two alternative synthetic pathways for obtaining a variety of functionalized double-decker silsesquioxanes with high yields based on the Pt catalysts were developed. These parallel routes concern reverse SiÀ H and À CH=CH 2 reactive groups placement in the doubledecker silsesquioxane core. As a result, a series of new tetrasubstituted double-decker silsesquioxanes derivatives were obtained with high yield and selectivity and comprehensively characterized in detail by spectroscopic analyses.[a] J.

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Section: Introductionmentioning

confidence: 99%

Highly Efficient Route for the Synthesis of a Novel Generation of Tetraorganofunctional Double‐decker Type of Silsesquioxanes

et al. 2019

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“…These research projects were expanded to a new member of a silsesquioxane family (i.e., a divinyl-substituted double-decker silsesquioxanes which were used as reactants in the silylative coupling and cross-metathesis (only for E = Ge) processes with a wide range of olefins, including highly π-conjugated arenes (Figure 21) [70,84,85,86]. It resulted in the development of a stereoselective method for the preparation of new molecular, dialkenyl-substituted DDSQ derivatives with a well-defined and documented structure (( E ) isomer of –HC=CH–).…”

Section: Catalytic Reactions Leading To Functionalized Silsesquioxmentioning

confidence: 99%

Synthetic Routes to Silsesquioxane-Based Systems as Photoactive Materials and Their Precursors

2019

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Over the past two decades, organic optoelectronic materials have been considered very promising. The attractiveness of this group of compounds, regardless of their undisputable application potential, lies in the possibility of their use in the construction of organic–inorganic hybrid materials. This class of frameworks also considers nanostructural polyhedral oligomeric silsesquioxanes (POSSs) with “organic coronae” and precisely defined organic architectures between dispersed rigid silica cores. A significant number of papers on the design and development of POSS-based organic optoelectronic as well as photoluminescent (PL) materials have been published recently. In view of the scientific literature abounding with numerous examples of their application (i.e., as OLEDs), the aim of this review is to present efficient synthetic pathways leading to the formation of nanocomposite materials based on silsesquioxane systems that contain organic chromophores of complex nature. A summary of stoichiometric and predominantly catalytic methods for these silsesquioxane-based systems to be applied in the construction of photoactive materials or their precursors is given.

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“…The presence of a methyl group at the vinylsilyl moiety was responsible for the lack of activity, which was consistent with earlier studies (Scheme 1). The scope of the reaction was further extended to the palette of olefins containing conjugated systems of π-bonds (Scheme 12) [24].…”

Section: Reviewmentioning

confidence: 99%

“…There are scarce reports on the application of ADMET in the synthesis of oligomers or polymers containing a POSS unit in the main chain. Marciniec disclosed ADMET copolymerization of DDSQ-2SiVi with dienes in the stereoselective synthesis of a new class of vinylene–arylene copolymers containing double-decker silsesquioxanes in the main chain (Scheme 18) [24].…”

Section: Reviewmentioning

confidence: 99%

Application of olefin metathesis in the synthesis of functionalized polyhedral oligomeric silsesquioxanes (POSS) and POSS-containing polymeric materials

Żak

Pietraszuk

2019

Beilstein J. Org. Chem.

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This mini-review summarizes the applications of olefin metathesis in synthesis and functionalization of polyhedral oligomeric silsesquioxanes (POSS) and POSS-containing polymeric materials. Three types of processes, i.e., cross metathesis (CM) of vinyl-substituted POSS with terminal olefins, acyclic diene metathesis (ADMET) copolymerization of divinyl-substituted POSS with α,ω-dienes and ring-opening metathesis polymerization (ROMP) of POSS-substituted norbornene (or other ROMP susceptible cycloolefins) are discussed. Emphasis was put on the synthetic and catalytic aspects rather than on the properties and applications of synthesized materials.

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Synthesis and characterization of functionalized molecular and macromolecular double-decker silsesquioxane systems

Abstract: Synthesis and characterization of new, molecular and macromolecular DDSQ-based compounds functionalized by substituted styrenes and distyrylarenes (also with heteroatoms) in a stereoselective manner is presented.

Cited by 35 publications

References 35 publications

Highly Efficient Route for the Synthesis of a Novel Generation of Tetraorganofunctional Double‐decker Type of Silsesquioxanes

Highly Efficient Route for the Synthesis of a Novel Generation of Tetraorganofunctional Double‐decker Type of Silsesquioxanes

Synthetic Routes to Silsesquioxane-Based Systems as Photoactive Materials and Their Precursors

Application of olefin metathesis in the synthesis of functionalized polyhedral oligomeric silsesquioxanes (POSS) and POSS-containing polymeric materials

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