Preparation and optical properties of hybrid sol–gel systems containg doubly anchored oligoarylenevinylenes

Corriu, Robert J. P.; Hesemann, Peter; Lanneau, G. F.

doi:10.1039/cc9960001845

Cited by 46 publications

(38 citation statements)

References 16 publications

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“…Up to now, OPV-based organosilane precursors have been synthesized by nucleophilic substitution between alkoxysilanes and organometallic intermediates, such as aryllithium and arylmagnesium reagents, or by a coupling reaction using alkoxysilyl-substituted benzene, ethylene, and styrene derivatives. [22,27] In the present synthetic procedures, Rh-catalyzed silylation was shown to be applicable to aromatic iodides that contain vinylene moieties and proceeds efficiently, which will lead to the development of various OPV-containing organosilane precursors.…”

Section: Synthesis Of Organosilane Precursorsmentioning

confidence: 99%

“…[18][19][20][21] If visible-light-responsive and highly emissive PMOs are obtained from OPV derivatives as transparent films, they are promising as a new class of phosphor materials. Although some phenylenevinylene-containing organosilane precursors and their polymers have been reported, [22][23][24][25][26][27] there has been no report on mesostructured films that consist of visible-light-responsive OPV-silica hybrid frameworks. The aim of the present work is to incorporate visible-lightresponsive and highly fluorescent OPV bridging groups within frameworks of mesostructured organosilica films.…”

Section: Introductionmentioning

confidence: 99%

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Highly Fluorescent Mesostructured Films that consist of Oligo(phenylenevinylene)–Silica Hybrid Frameworks

Mizoshita

Goto

Tani

et al. 2008

Adv Funct Materials

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Highly fluorescent and visible‐light‐responsive mesostructured organosilica films are successfully obtained by acidic sol–gel polycondensation of oligo(phenylenevinylene) (OPV)‐bridged organosilane and tetraethoxysilane precursors in the presence of a template surfactant. The OPV‐bridged organosilane precursors with different lateral alkoxy substituents, hexyloxy and 2‐ethylhexyloxy, and no substituent, are synthesized by Rh‐catalyzed silylation of corresponding aromatic iodides. From the organosilane precursors, three kinds of mesostructured OPV–silica hybrid films are prepared by spin‐casting using evaporation‐induced self‐assembly. UV‐vis absorption and fluorescence behavior of the OPV–silica hybrid films show that the optical properties and intermolecular interactions of the OPV moieties embedded within the organosilica frameworks strongly depend on the lateral alkoxy substituents in the precursors. The hexyloxy and 2‐ethylhexyloxy substituents prevent aggregation of the OPV units in the organosilica frameworks; this result leads to high fluorescence quantum yields of 0.48–0.61 and 0.63–0.66, respectively, while non‐substitution leads to lower fluorescence quantum yields of 0.25–0.34. Fluorescence decay profiles of the organosilica hybrid films also confirm a suppression of the aggregation of OPV moieties by the lateral substituents. These mesostructured organosilica films with significant optical properties in the visible‐light region are promising as a new class of phosphor materials.

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Section: Synthesis Of Organosilane Precursorsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Highly Fluorescent Mesostructured Films that consist of Oligo(phenylenevinylene)–Silica Hybrid Frameworks

Mizoshita

Goto

Tani

et al. 2008

Adv Funct Materials

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“…General: All reagents and solvents were of the highest commercial quality and were used without further purification. The cationic surfactant C 18 TMACl was purchased from TCI. The naphthalene-based precursor BTENph was synthesized by the Rh-catalyzed silylation of 2,6-dibromonaphthalene, as reported previously, [21,27] and obtained in an improved yield.…”

Section: Methodsmentioning

confidence: 99%

“…Keywords: fluorescence · hybrid materials · mesoporous materials · organosilicates · self-assembly scale ordering on the chemical and physical properties of the organic moieties embedded within the frameworks, although there have not been any reports on this issue. [16][17][18][19][20][21] In addition, it is also important to expand the number of organic groups to form crystal-like ordering of pore walls for the development of further functionalized PMOs.…”

Section: Introductionmentioning

confidence: 99%

Fluorescence Emission from 2,6‐Naphthylene‐Bridged Mesoporous Organosilicas with an Amorphous or Crystal‐Like Framework

Mizoshita

Goto

Kapoor

et al. 2008

Chemistry A European J

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We report that 2,6-naphthylene-bridged periodic mesoporous organosilicas exhibit unique fluorescence behavior that reflects molecular-scale periodicities in the framework. Periodic mesoporous organosilicas consisting of naphthalene-silica hybrid frameworks were synthesized by hydrolysis and condensation of a naphthalene-derived organosilane precursor in the presence of a template surfactant. The morphologies and meso- and molecular-scale periodicities of the organosilica materials strongly depend on the synthetic conditions. The naphthalene moieties embedded within the molecularly ordered framework exhibited a monomer-band emission, whereas those embedded within the amorphous framework showed a broad emission attributed to an excimer band. These results suggest that the naphthalene moieties fixed within the crystal-like framework are isolated in spite of their densely packed structure, different from conventional organosilica frameworks in which only excimer emission was observed for both the crystal-like and amorphous frameworks at room temperature. This key finding suggests a potential to control interactions between organic groups and thus the optical properties of inorganic/organic hybrids.

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“…We have supposed that this slight discrepancy results from a partial Si-C bond cleavage occurring during the synthesis processes, though aromatic carbon-silicon hydrolysis have never been observed in the literature under mild synthetic conditions. 2a,b,6c, [8][9][10][11] Now, the Si-C hydrolysis was actually observed during the phenylene-bridged material preparation when the sol-gel reaction required drastic conditions such as strongly basic 4a or acidic 12 conditions, hydrothermal procedures 13 or when the PMOS was treated at very high temperatures.…”

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confidence: 99%

Si–C attachment points during sol–gel synthesis of organosilicas from 2,8-bis-silylated Tröger's base as building block precursor

et al. 2011

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The porous organosilica framework containing Tr€ oger's base (TB) prepared by mild sol-gel synthesis from 2,8-bis-silylated TB precursor contains a mixture of two point attached TB and one point attached TB units, resulting from unexpected partial Si-C bond cleavage as demonstrated by 29 Si MAS NMR spectroscopy and by selective chemo-desorption of the anchored organic part of the hybrid material.

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Preparation and optical properties of hybrid sol–gel systems containg doubly anchored oligoarylenevinylenes

Cited by 46 publications

References 16 publications

Highly Fluorescent Mesostructured Films that consist of Oligo(phenylenevinylene)–Silica Hybrid Frameworks

Highly Fluorescent Mesostructured Films that consist of Oligo(phenylenevinylene)–Silica Hybrid Frameworks

Fluorescence Emission from 2,6‐Naphthylene‐Bridged Mesoporous Organosilicas with an Amorphous or Crystal‐Like Framework

Si–C attachment points during sol–gel synthesis of organosilicas from 2,8-bis-silylated Tröger's base as building block precursor

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