Vibrational spectra of a ferrocenyl phosphine derivative chemisorbed on 3-aminopropylsilyl modified silica gel

Ivanovski, Vladimir; Bukleski, Miha; Madalska, Martyna; Hey‐Hawkins, Evamarie

doi:10.1016/j.vibspec.2013.09.009

Cited by 7 publications

(7 citation statements)

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“…Ivanovski et al investigated the region of the OH stretching vibrations of silica gel activated at different temperatures for the purpose of checking the availability of the OH groups for further reaction with 3-aminopropyltrimethoxysilane (APTMS) molecules and whether chemisorption was successful, finding evidence whether chemisorption of APTMS involves all available methoxy groups. It is also possible to investigate the conformation of the aminopropyl groups (APS) backbone on the silica gel surface and the possible proton transfer between the NH 2 groups of APS and OH from silica gel detected by the formation of NH 3 + and SiO − which is spectroscopically detectable through the appearance of the δ(NH 3 + ) vibrations at 1668 cm −1 [49]. In addition, Bukleski et al developed a direct quantitative method of quantification of maximal chemisorption of 3-aminopropylsilyl groups on silica gel using [45].…”

Section: Applications Of Molecular Spectroscopy To Current Research Imentioning

confidence: 99%

Fourier Transform Infrared and Raman Characterization of Silica-Based Materials

Capeletti¹,

Zimnoch²

2016

Applications of Molecular Spectroscopy to Current Research in the Chemical and Biological Sciences

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Fourier Transform Infrared and Raman are powerful techniques to evaluate silica and hybrid silica structure. It is possible to evaluate the silica network formation along the hydrolysis and condensation reactions in terms of siloxane rings formation and Si-O(-Si) angle deformation due to the introduction of organic groups, the employed synthetic route or encapsulated species interaction. The siloxane four-or six-membered rings imply in a more rigid or flexible network, respectively, in order to accommodate the organic groups. A structural analysis of the materials is of high importance, since interactions between the encapsulated molecules and the matrix are critical for the device performance, such as sensors. This type of device needs the permeation of an analyte to activate the encapsulated receptor molecules inside the silica structure. Fourier transform infrared spectrometry can be also used to determine parameters of the silica network as a function of the hydrophilicity/hydrophobicity degree and the siloxane ring structure with respect to thin film porosity. This silica structural analysis is reviewed along the text in a tentative of better exploring the data resulting from these powerful techniques. In addition, the functionalization of silica structures by the use of organoalkoxysilanes, which is important to the creation of high-specific materials, can be well described by these two complementary techniques. The Si-C bonds and the maintenance of the organic substituents such as methyl, octyl, octadecyl, vinyl, phenyl, aminopropyl, mercaptopropyl, isocyanatopropyl, iodopropyl, chloropropyl and glicydoxypropyl could be evaluated after the sol-gel synthesis process. The literature regarding silica vibrational spectroscopy is also explored creating a data bank of wave numbers for the most important bonds for different types of silica and hybrid silica materials obtained by different synthetic routes.

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Section: Applications Of Molecular Spectroscopy To Current Research Imentioning

confidence: 99%

Fourier Transform Infrared and Raman Characterization of Silica-Based Materials

Capeletti¹,

Zimnoch²

2016

Applications of Molecular Spectroscopy to Current Research in the Chemical and Biological Sciences

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“…The progress of the condensation reaction between the carboxaldehyde groups and the primary amines was followed by IR spectroscopy. , The absorbance IR spectra of APS-functionalized silica gel recorded in the range of 1500–1700 cm –1 showed two strong vibration bands at 1598 (δ(NH 2 )) and 1668 cm –1 (δ asm. (NH 3 + )).…”

Section: Resultsmentioning

confidence: 98%

“…For the following immobilization studies, functionalization of the solid support (silica gel) with commercially available 3-aminopropyltrimethoxysilane (APTMS) was conducted . The reactive NH 2 group undergoes a fast and selective condensation reaction with carboxaldehydes, yielding only water as a side product.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of 1,1′,2-Trisubstituted Aryl-Based Ferrocenyl Phosphines as Precursors for Immobilized Ligands

et al. 2013

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Ferrocenylaryl or ferrocenylheteroaryl phosphines bearing a carboxaldehyde group, [Fe{1-PPh2(spacer)-2-NMe2CH2C5H3}(C5H4CHO)] (spacer = none (rac-12), 1,4-phenylene (rac-13), 1,3-phenylene (rac-14), 2,5-thienylene (rac-15)), were prepared in a facile four-step sequence starting with dibromination of N,N-dimethylaminomethylferrocene (1) followed by Negishi cross-coupling between 1,1′-dibromo-2-N,N-dimethylaminomethylferrocene (rac-2) and aryl or heteroaryl bromide phosphine oxides, Br-spacer-P(O)Ph2 (spacer = 1,4-phenylene, 1,3-phenylene, 2,5-thienylene), reduction with trichlorosilane, and functionalization of the 1′-position of the cyclopentadienyl ring. All products were fully characterized by spectroscopy (1H, 13C, and 31P NMR, MS, IR) and for rac-3, rac-7 and rac-11 also by X-ray crystallography. Furthermore, preliminary studies on the grafting of rac-12 on silica were conducted.

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“…A particular feature in the DRIFT spectra of silica gel is the band at 3747 cm -1 , which originates from the stretching vibrations of the isolated free OH groups [2,8,31,32]. The free OH groups come into interaction with the MeO groups from the APTMS and chemical Si-O-Si bond is formed as shown in the case of monodentate bonding by the equation: The process of chemisorption leads to a decreasing intensity of the band at 3747 cm -1…”

Section: Chemisorption Of Aptms On Silica Gelmentioning

confidence: 99%

Indirect quantitative IR assessment of maximal monomolecular deposition of 3-aminopropyltrimethoxysilane on silica gel surface

Bukleski

Ivanovski

2014

Maced. J. Chem. Chem. Eng.

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Quantification of the amount of maximum loaded 3-aminopropylsilyl (APS) on a thermally pretreated silica gel (600 ºC) was performed using IR spectroscopy. Finding the maximum load through a construction of a Langmuir isotherm was not possible due to the irreversibility of the chemisorption reaction. The method used in this work was based on the analysis of the toluene solution on the quantity of the non-reacted 3-aminopropyltrimethoxysilane (APTMS) after the saturation of the silica gel surface with APS. The process of chemisorption was monitored via the increasing band intensity of (CH 2 ), (NH 2 ), and (NH 2 ) modes of the adsorbent and decreasing (OH) band intensity characteristic for the free isolated OH groups of silica gel using DRIFT spectroscopy. The results on maximum adsorption are in line with those previously obtained, using carbon elemental analysis and a direct DRIFT method.Keywords: 3-aminopropyltrimethoxysilane (APTMS); chemisorption; DRIFT spectra; modified silica gel ИНДИРЕКТНО КВАНТИТАТИВНО ОПРЕДЕЛУВАЊЕ МАКСИМАЛНА МОНОМОЛЕКУЛАРНА ДЕПОЗИЦИЈА НА 3-АМИНОПРОПИЛТРИМЕТОКСИСИЛАН НА ПОВРШИНАТА ОД СИЛИКАГЕЛ СО ИНФРАЦРВЕНА СПЕКТРОСКОПИЈАКвантификацијата на максимално нафатеното количество 3-аминопропилсилил (APS) на температурно активиран силикагел (600 ºC) беше спроведена со помош на инфрацрвена спектроскопија. Определувањето на максимално нафатеното количество преку конструкција на Лангмјурова изотерма не е можно како резултат на иреверзибилноста на хемиската реакција. Користениот метод во оваа работа беше базиран на анализа на растворот од толуен во однос на содржината на неизреагиран 3-аминопропилтриметоксисилан (APTMS) по заситувањето на површината на силикагелот со групи на APS. Процесот на хемисорпција беше следен преку зголемувањето на интензитетот на лентите од модовите на(CH 2 ), (NH 2 ) и (NH 2 ) од атсорби-раните молекули и намалувањето на интензитетот на модот(OH) од слободните, т.е. изолирани OH-групи од силикагелот, со помош на DRIFT спектроскопијата. Добиените резултати за максималната атсорпција се во согласност со претходно добиените од елементарна анализа и со оние добиени со примена на директниот DRIFT-метод.Клучни зборови: 3-аминопропилтриметоксисилан (APTMS); хемисорпција; DRIFT спектри; модифициран силика гел M. Bukleski, V. Ivanovski Maced.

show abstract

Vibrational spectra of a ferrocenyl phosphine derivative chemisorbed on 3-aminopropylsilyl modified silica gel

Cited by 7 publications

References 22 publications

Fourier Transform Infrared and Raman Characterization of Silica-Based Materials

Fourier Transform Infrared and Raman Characterization of Silica-Based Materials

Synthesis of 1,1′,2-Trisubstituted Aryl-Based Ferrocenyl Phosphines as Precursors for Immobilized Ligands

Indirect quantitative IR assessment of maximal monomolecular deposition of 3-aminopropyltrimethoxysilane on silica gel surface

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