First Phenylenevinylene Based Organogels:  Self-Assembled Nanostructures via Cooperative Hydrogen Bonding and π-Stacking

Ajayaghosh, Ayyappanpillai; George, Subi J.

doi:10.1021/ja005933+

Cited by 373 publications

(208 citation statements)

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“…to form three dimensional gel networks in nonpolar solvents. [56] Later, these researchers described the encapsulation of rhodamine B (11), within the gel's three-dimensional network for the purpose of light harvesting studies. [57] They demonstrated thermoreversible fluorescenceresonance energy transfer (FRET) from OPV-based gels to the encapsulated dye.…”

Section: Gel Matrices and Energy Transfermentioning

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: Gel Matrices and Energy Transfermentioning

confidence: 99%

Improving the Properties of Organic Dyes by Molecular Encapsulation

2005

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“…[3][4][5][6][7][8][9][10][11] Because π-conjugated compounds tend to aggregate by π-π stacking, the introduction of non-covalent interactions at appropriate positions increases their association constants and facilitates the formation of higher-ordered structures. 12,13 For example, supramolecular gels can be formed through intermolecular interactions such as hydrogen bonds, 14,15 and multiple long alkyl chains facilitate columnar stacking along the π-stacking direction of supramolecular assemblies [16][17][18][19] (Figure 1a). A variety of assembled structures can be formed through covalent linkages between π-conjugated units (Figure 1b).…”

Section: Introductionmentioning

confidence: 99%

π-Conjugated polymer-layered structures: synthesis and self-assembly

Tsuji

Morisaki

Chujo

2016

Polym J

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π-Conjugated polymers capped with a boronic acid end-functional group were synthesized by chain-growth Suzuki-Miyaura polycondensation. The obtained polymers were reacted with a π-stacked-polymer scaffold, developed in our previous work. Despite their bulkiness, the conjugated polymers were efficiently introduced into the polymer scaffold. The spectroscopic and optical characterization of the obtained graft polymers in the solid state revealed that the original π-conjugated polymers were stacked in a single polymer chain. Although excluded volume effects prevented significant intermolecular interactions between the polyfluorenes, the introduced polythiophenes formed intermolecular π-stacked structures. Direct observations of the obtained graft polymers showed that the graft polymers self-assembled into the spherical or fiber structures depending on the introduced polymers, whereas no ordered structures were formed by the same polymers before the polymer reaction.

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“…[126][127][128] Commonly used organogelators include carbohydrate derivatives, [129] amphiphilic molecules, [130] substituted cyclohexane, [131] and cholesterol derivatives. [132] Usually, long alkyl chains or steroidal groups are incorporated into most gelator molecular structures to achieve effective gelation, although these structural elements are normally inactive and undesirable for the optoelectronic properties.…”

Section: Self-assembly Through Organogelationmentioning

confidence: 99%

Low‐Dimensional Nanomaterials Based on Small Organic Molecules: Preparation and Optoelectronic Properties

et al. 2008

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This article presents a comprehensive review of recent progress of research dedicated to low‐dimensional nanomaterials constructed from functional low‐molecular‐weight organic compounds, whose optoelectronic properties are fundamentally different from those of their inorganic counterparts. After introducing the development of inorganic and organic macromolecular nanomaterials, we begin with a general review of the construction strategies for achieving both zero‐dimensional (0D) and one‐dimensional (1D) nanostructures from small organic functional molecules. We then provide an overview of the unique optoelectronic properties induced by molecular aggregation in the nanostructures. Special emphasis is put on the luminescent properties that are different from those of the corresponding bulk materials, such as aggregation‐induced enhanced emission, fluorescence narrowing, multicolor emission, and tunable and switchable emissions from doped nanostructures. We conclude with a summary and our personal view of the direction of future development of organic opto‐functional nanomaterials and devices.

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First Phenylenevinylene Based Organogels: Self-Assembled Nanostructures via Cooperative Hydrogen Bonding and π-Stacking

Cited by 373 publications

References 20 publications

Improving the Properties of Organic Dyes by Molecular Encapsulation

Improving the Properties of Organic Dyes by Molecular Encapsulation

π-Conjugated polymer-layered structures: synthesis and self-assembly

Low‐Dimensional Nanomaterials Based on Small Organic Molecules: Preparation and Optoelectronic Properties

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