Molecular sieve encapsulated organic dyes and metal chelates

Wöhrle, Dieter; Schulz‐Ekloff, G.

doi:10.1002/adma.19940061119

Cited by 88 publications

(32 citation statements)

References 37 publications

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“…[46] The lower reactivity was attributed to the molecular sieves deactivating the energy transfer from dye triplet state to O 2 . In 1995, Monte and Levy encapsulated near-IR dyes such as oxazine and cyanine dyes in sol-gel matrices and produced dye-doped glasses.…”

Section: Inorganic Matricesmentioning

confidence: 99%

Improving the Properties of Organic Dyes by Molecular Encapsulation

2005

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There is a demand for new methods of protecting organic dyes from aggregation effects and photochemical degradation. The purpose of this microreview is to summarize the recent attempts to improve the properties of dyes by molecular encapsulation. Organic dyes have been encapsulated inside inorganic matrices such as molecular sieves, and molecular containers such as cyclodextrins, cucurbiturils, dendrimers, and self-assembled gels. Another strategy is perma- IntroductionOrganic chromophores such as cyanines, squaraines, azo dyes and perylenediimide dyes are widely used as pigments in many commercial products. They are active ingredients in semiconducting materials, [1] textile products, [2] laser materials, [3] optical disks, [4] paints, [5] and probes for biological systems.[6] Modern research on organic dyes includes investigations of building blocks for conjugated polymers, hydrogen bonded assemblies, chromogenic sensors, molecular shuttles, solar energy cells, photonics and various approaches to photodynamic therapy. [7][8][9][10][11] A common limitation with organic dyes, especially those with long-wavelength absorption bands, is their susceptibility to chemical and photochemical degradation. The reason for the enhanced reactivity is the inherently small HOMO-LUMO energy gap, which means that the dyes are potentially reactive with both nucleophiles and electrophiles. Another potential drawback with organic dyes is their tendency to aggregate, which induces multichromophoric interactions that alter the color quality and quench the photoluminescence. In principle, these problems can be attenuated by supramolecular encapsulation strategies that isolate the individual dye molecules and prevent self-aggregation or similar interactions with the chemical environment. The purpose of this microreview is to summarize the recent literature on meth- Germany, 2005) ods to improve the properties of organic dyes by molecular encapsulation. The focus is on relatively "robust" molecular containers and does not include "soft" assemblies like micelles, emulsions or vesicles.

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Section: Inorganic Matricesmentioning

confidence: 99%

Improving the Properties of Organic Dyes by Molecular Encapsulation

2005

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“…UV-vis spectra of solutions were measured using a Perkin-Elmer Lambda 2 spectrometer. 1 H NMR spectra were measured at 360 MHz on a Brucker WH 360 (Aspect 3000). Mass spectra were obtained using a Finnigan MAT 8222.…”

Section: Characterizationmentioning

confidence: 99%

“…Four principal methods for the uniform incorporation of dyes or metal complexes in the molecular sieve have been described [1]. The method to be used depends on the charge, stability and solubility of the guest molecule.…”

Section: Introductionmentioning

confidence: 99%

“…The dyes are added to the gel before the hydrothermal synthesis. Negatively charged (1)(2)(3)(4)(5), positively charged (6)(7)(8) and hydrophobic uncharged (9,10) phthalocyanines were employed (Scheme 1). A recent report described the encapsulation of unsubstituted Zn(II) phthalocyanine into Si-, Al-and Ti-MCM-41 [26] by adding the Zn complex to the gel mixture.…”

Section: Introductionmentioning

confidence: 99%

“…Novel composite materials based on molecular sieves such as zeolites and AlPO 4 -5 have been increasingly studied in recent years, where a wide range of encapsulated guests such as dyes [1], metal complexes [2], polymers [3], metal clusters [4] and semiconductor nanoclusters [5] have been used. The molecular sieve framework represents a host material exhibiting a higher stability against organic solvents, acids and bases as well as a higher resistance to temperature and radiation than organic polymers.…”

Section: Introductionmentioning

confidence: 99%

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Incorporation of Differently Substituted Phthalocyanines into the Mesoporous Molecular Sieve Si-MCM-41

Ganschow

Wöhrle

Schulz‐Ekloff

1999

J. Porphyrins Phthalocyanines

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Substituted phthalocyanine Zn complexes exhibiting negative, positive or no charge are incorporated in the mesopores of Si -MCM-41 materials during hydrothermal synthesis in the presence of cetyltrimethylammonium chloride. The nature of the intermolecular interaction between the surfactant micelle and the capped chromophores determines (i) the resistance of the dye towards hydrolytic degradation during the synthesis and (ii) its stability of anchoring towards extraction with ethanol in the composite material. Loadings up to 2 × 10−5 mol/g molecular sieve are achieved, corresponding to an average distance between the encapsulated dye molecules between 2 and 3 nm. The UV-vis spectra reveal the non-aggregated state of the chromophores, pointing to a uniform distribution and a perfect separation by the surfactant molecules.

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Porphyrins, phthalocyanines and related systems in polymer phases

Wöhrle

2000

J. Porphyrins Phthalocyanines

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Macrocyclic ring systems in polymer phases described in this overview are part of the field of macromolecular metal complexes. In this review, first, examples of porphyrins in protein environments being active in biological systems are given. These biological sites are essential to understand the functions of artificial systems. Then a classification and examples of synthetic macromolecular metal complexes based on porphyrins, phthalocyanines and related systems are described.

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Molecular sieve encapsulated organic dyes and metal chelates

Cited by 88 publications

References 37 publications

Improving the Properties of Organic Dyes by Molecular Encapsulation

Improving the Properties of Organic Dyes by Molecular Encapsulation

Incorporation of Differently Substituted Phthalocyanines into the Mesoporous Molecular Sieve Si-MCM-41

Porphyrins, phthalocyanines and related systems in polymer phases

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