Covalent attachment of dye molecules to the inner surface of MCM-41

Rohlfing, Yven; Wöhrle, Dieter; Wark, Michael; Schulz‐Ekloff, G.; Rathouský, Jiřı́; Zukal, Arnošt

doi:10.1016/s0167-2991(00)80226-8

Cited by 14 publications

(6 citation statements)

References 15 publications

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“…76, 77 The solid state 29 Si CP/MAS NMR for the MCM-41 was also consistent with the reported data 78 and shows three characteristic resonances for the different silicon sites as calculated by the general formula: Q n = Si(OSi) n (OH) 4-x ; where Q 2 = geminal silanol groups ((OH) 2 *Si(OSi) 2 ), Q 3 = isolated silanol group (OH*Si(OSi) 3 ) and Q 4 = framework silicon (*Si(OSi) 4 ) (Fig. 79 The detailed presilylation procedure is given in the experimental section. The peaks were assigned to the silicon sites of Q 2 (d 93.…”

Section: Chemical Modification Of Mcm-41mentioning

confidence: 55%

“…(See ESI †) The powder X-ray diffraction pattern for MCM-41, shows a typical pattern with a high degree of long range ordering of the structure. 9, 79 The schematic illustration of the selective presilylation process and thereafter the immobilisation of catalysts are given in Scheme 3. 2).…”

Section: Chemical Modification Of Mcm-41mentioning

confidence: 99%

“…76, 77 The solid state 29 Si CP/MAS NMR for the MCM-41 was also consistent with the reported data 78 it can be supposed that there is a difference in the inner and outer surface on MCM-41. 9, 79 The schematic illustration of the selective presilylation process and thereafter the immobilisation of catalysts are given in Scheme 3. In a typical presilylation process, dried MCM-41 was treated with a standard amount of Ph 2 SiCl 2 (0.02 mL g -1 MCM-41) according to the established literature procedures.…”

Section: Chemical Modification Of Mcm-41mentioning

confidence: 99%

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Heterogenised N-heterocyclic carbene complexes: synthesis, characterisation and application for hydroformylation and C–C bond formation reactions

2011

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The imidazolium salts: 1-mesityl-3-(3-trimethoxysilylpropyl)imidazolium iodide and 1-tert-butyl-3-(3-trimethoxysilylpropyl)imidazolium iodide, abbreviated as (tmpMes)HI (3a) and (tmp(t)Bu)HI (3b), respectively, have been synthesised. The palladium(ii) complexes (η(3)-C(3)H(5)) (tmpMes)PdCl (5a) and (η(3)-C(3)H(5))(tmp(t)Bu)PdCl (5b), rhodium(i) and iridium(i) complexes (η(4)-1,5-COD) (tmpMes)MCl, M = Rh (6a), Ir (7a) and (η(4)-1,5-COD)(tmp(t)Bu)MCl, where M = Rh (6b), Ir (7b), were synthesised by silver transmetallation reactions using the silver(i) complexes (tmpMes)AgI (4a) and (tmp(t)Bu)AgI (4b). The iridium complex 7b has been structurally characterised. The Pd(ii) and Rh(i) complexes have been immobilised by attachment to chemically modified MCM-41. The immobilised palladium(ii) materials have been tested as recyclable catalysts for Suzuki type C-C bond formation reactions in water and the immobilised rhodium(i) materials have been examined for their catalytic ability for the hydroformylation of 1-octene.

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Section: Chemical Modification Of Mcm-41mentioning

confidence: 55%

Section: Chemical Modification Of Mcm-41mentioning

confidence: 99%

Section: Chemical Modification Of Mcm-41mentioning

confidence: 99%

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Heterogenised N-heterocyclic carbene complexes: synthesis, characterisation and application for hydroformylation and C–C bond formation reactions

2011

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“…For a typical MCM-41 material, the mesopores surface area (S meso ) is estimated as 1049 m 2 /g, whereas the external surface area (S external ) reaches 89 m 2 /g. 73 We can, hence, estimate the maximal in-pore adsorption as S meso /S total = 92%. According to Figure 6, the ball-milling with the BA@ MCM-41 weight ratio of 1:2 allows one to reach this limit, with the Y contribution found at the level of ca.…”

Section: Resultsmentioning

confidence: 99%

Mapping of Guest Localization in Mesoporous Silica Particles by Solid-State NMR and Ab Initio Modeling: New Insights into Benzoic Acid and p-Fluorobenzoic Acid Embedded in MCM-41 via Ball Milling

et al. 2021

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We present a novel strategy for mapping the localization of guest molecules (GMs) in mesoporous materials by combining mechanochemistry with solid-state nuclear magnetic resonance (ssNMR) spectroscopy. To this end, we consider model guest–host systems of benzoic acid (BA) and para-fluorobenzoic acid (4-FBA) embedded in mesoporous MCM-41 material and examine the recently proposed loading (MeLo) procedure for efficient encapsulation of molecular species. Application of high-resolution NMR experiments (1H and 19F NMR) has allowed detection of a multimodal distribution of the spectral signals ascribed to embedded GMs. This peculiarity reflects the presence of distinct molecular ensembles subjected to intrinsically different local environments and exhibiting different dynamical behavior. Furthermore, a considerable fraction of an amorphous phase has been found as a byproduct of the ball-milling. The stability of the phase mixture was further checked by subjecting the samples to chemical and physical stimuli, and a detailed interpretation of the NMR data was corroborated by theoretical calculations. To this end, we have undertaken a challenge to predict the NMR spectra of the GMs@MCM-41 using advanced ab initio molecular dynamics (AIMD) simulations, providing an accurate and exhaustive analysis of the NMR spectra. On the basis of the ab initio modeling validated against the experimental results, we find that the multimodal signal distribution reflects the level of the pore filling, and can be ascribed to the presence of both interface and fluid molecular species trapped inside the pores. This has been confirmed for both BA@MCM-41 and 4-FBA@MCM-41 systems. The presence of the third, amorphous fraction can be linked to interstitial space between randomly ordered crystallites, pointing at the importance of the external surface in further stabilization of encapsulated materials. Altogether, a consistent experimental and theoretical methodology has been presented, paving the way for a more accurate analysis of complex nanoconfined systems.

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“…Schulz-Ekloff et al successfully bound the sulfochloride of Rhodamine B (RhB) with the internal pore wall of MCM-41. The internal pore wall was beforehand modified with aminopropyl groups [4]. The naphthalene urea fluorescent receptor was also immobilized on the mesoporous silica by Seo et al [5].…”

Section: Introductionmentioning

confidence: 99%

Anchoring of 1,8-naphthalimide derivative into mesoporous MCM-41 molecular sieves

et al. 2011

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The fluorescent dye molecules, 4-piperidine-1,8-naphthalimide, were successfully fixed into the amino modified pore channel of mesoporous MCM-41 type materials by in situ reaction of 4-piperidinyl-1,8-naphthalic anhydride with the amino group. The formation of amide bonds on the pore surface was verified by infrared spectra. The maximum fluorescence emission peak of this hybrid material has a red shift of 13 nm compared to that of a naphthalimide derivative in ethanol solution. Moreover, the fluorescence intensity of dye molecules grafted into Ce-doped MCM-41 is higher than that in pure silica MCM-41. This phenomenon is attributed to the inhibited internal electron transfer from piperidine to naphthalimide groups by Ce 4? , thus improving the fluorescence intensity of the naphthalimide group. The unique fluorescence behavior of the 1,8-naphthalimide derivative doped hybrid mesoporous material makes it a good candidate for the metal ions microdetection.

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Covalent attachment of dye molecules to the inner surface of MCM-41

Cited by 14 publications

References 15 publications

Heterogenised N-heterocyclic carbene complexes: synthesis, characterisation and application for hydroformylation and C–C bond formation reactions

Heterogenised N-heterocyclic carbene complexes: synthesis, characterisation and application for hydroformylation and C–C bond formation reactions

Mapping of Guest Localization in Mesoporous Silica Particles by Solid-State NMR and Ab Initio Modeling: New Insights into Benzoic Acid and p-Fluorobenzoic Acid Embedded in MCM-41 via Ball Milling

Anchoring of 1,8-naphthalimide derivative into mesoporous MCM-41 molecular sieves

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