2014
DOI: 10.1002/chem.201404153
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High‐Yield Synthesis of Amido‐Functionalized Polyoctahedral Oligomeric Silsesquioxanes by Using Acyl Chlorides

Abstract: Homosubstituted amido-functionalized polyoctahedral oligomeric silsesquioxanes (POSS) have been synthesized by using acyl chlorides in high yields (ca. 95%). The method proved to be superior over "conventional" syntheses applying carboxylic acids or acid anhydrides, which are much less efficient (ca. 60% yield). A palette of aryl and alkyl groups has been used as side-chains. The structures of the resulting amide-POSS are supported by multinuclear (1)H, (13)C, (29)Si NMR and FTIR spectroscopy and their full co… Show more

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Cited by 31 publications
(39 citation statements)
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“…24,27 The thermal properties of 1-6 were examined by thermal gravimetric analysis (TG-DTA) performed under air and dinitrogen and by differential scanning calorimetry (DSC) under anaerobic conditions (He). 24,27 The thermal properties of 1-6 were examined by thermal gravimetric analysis (TG-DTA) performed under air and dinitrogen and by differential scanning calorimetry (DSC) under anaerobic conditions (He).…”
Section: Thermal Propertiesmentioning
confidence: 99%
“…24,27 The thermal properties of 1-6 were examined by thermal gravimetric analysis (TG-DTA) performed under air and dinitrogen and by differential scanning calorimetry (DSC) under anaerobic conditions (He). 24,27 The thermal properties of 1-6 were examined by thermal gravimetric analysis (TG-DTA) performed under air and dinitrogen and by differential scanning calorimetry (DSC) under anaerobic conditions (He).…”
Section: Thermal Propertiesmentioning
confidence: 99%
“…This compound was prepared with a method based on a previously reported procedure. 18 Concentrated HCl (200 mL, 236 g, 2.32 mol, 3.6 eq) was carefully added to a continuously stirred solution of (3-aminopropyl)triethoxysilane 55 (150 mL, 139.4 g, 0.641 mol) in MeOH (1.2 L) in a 2.0 L roundbottom flask. The flask was capped and the solution was stirred at room temperature for 4 weeks at 25 °C.…”
Section: Synthesismentioning
confidence: 99%
“…Chromium(III) acetylacetonate was prepared following the described procedure. 18 Synthesis of octa and deca(3-decanamidopropyl)silsesquioxanes 4 and 5 was carried 70 out under nitrogen gas flow, in a Schlenk line. Glassware was predried at 120 °C.…”
Section: Introductionmentioning
confidence: 99%
“…In 29 Si NMR, only one signal assigned to the silicon nucleus at approximately d = À66.6 ppm was observed, confirming the formation of an alkyl-substituted cubic POSS. Also, the formation of a hexahedral structure possessing terminal CH 2 (2) constantly evolves in solution, applying 1 allowed us to obtain molecular 2 in situ, avoiding drawbacks such as cage-opening rearrangements and other side reactions such as the formation of bigger T n (where n is 10 and/or 12) spherosilicates and random silanes. 3 Because of the above-mentioned arguments, it is much more convenient from a synthetic point of view to generate 2 in an immediate one-pot transformation starting from ionic salt 1 directly before further investigations.…”
Section: Synthesis and Characterization Of The Starting Materialsmentioning
confidence: 99%
“…Among fully functionalized POSSs such as T 8 , T 10 , or T 12 containing 8, 10, or 12 silicon atoms, respectively, most interest has been focused on cubic spherosilicates (hexahedral octafunctionalized silsesquioxanes, T 8 ). [2][3][4] Their attractiveness derives from the fact that they are highly soluble in common organic solvents making them useful compounds for the construction of numerous well-defined hybrid materials. Such compounds can effectively anchor various reactive substituents, R, to the siloxane core and, in fact, the structural and physicochemical properties as well as the potential applications of the POSSs are directly related to the precisely designed side chains.…”
Section: Introductionmentioning
confidence: 99%