Self‐Assembled Vesicles from an Amphiphilic <i>ortho</i>‐Phenylene Ethynylene Macrocycle

Seo, Sang Hyuk; Chang, Ji Young; Tew, Gregory N.

doi:10.1002/ange.200600688

Cited by 43 publications

(16 citation statements)

References 68 publications

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“…In the process of self-assembly, the hydrophobic OPE spacer should be arranged inside the membrane of the vesicles by p-p stacking, whereas the relatively polar cholate groups should be exposed to the solvent. This is similar to the packing model of p-conjugated, macrocycle-derived vesicles reported by Tew et al [16] It is reasonable that the hydro-and lipophilic sides of cholic acid meet together to yield a continuous membrane structure. If this is the case, there would be many hydroxyl groups on the surface of the membrane, which is consistent with the fact that the vesicles tend to stick together due to the formation of hydrogen bonds.…”

Section: Mechanism Of Self-assemblysupporting

confidence: 89%

Unique Twisted Ribbons Generated by Self‐Assembly of Oligo(p‐phenylene ethylene) Bearing Dimeric Bile Acid Pendant Groups

Wang

et al. 2009

Chemistry A European J

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Let's twist again! Remarkable broad and twisted ribbons were generated from the self-assembly of oligo(p- phenylene ethylene) (OPE) bearing dimeric deoxycholic acid pendant groups (see graphic). Varying the bile acid led to nanostructures with drastically different morphologies. The distinctive aggregate shapes of these steroid-OPE conjugates are attributed to the subtle differences in their molecular structures.A series of novel oligo(p-phenylene ethynylene) (OPE) derivatives bearing dimeric cholic acid (OPE1), deoxycholic acid (OPE2) and lithocholic acid (OPE3) was synthesized. The self-assembly behavior of these derivatives were systematically studied and compared in a THF/water solvent mixture. The addition of water to THF can induce the helical stacking of oligo(p-phenylene ethylene) bearing dimeric deoxycholic acid end groups, which leads to highly interesting twisted assemblies. Variation of the bile acid group led to nanostructures with drastically different morphologies. The application of spectroscopy in combination with X-ray diffraction techniques provided a reasonable view of the final self-assembled structures. The observed distinctive aggregate shapes and the preference in the type of molecular packing of these steroid-OPE conjugates are attributed to the subtle differences in their molecular features.

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Section: Mechanism Of Self-assemblysupporting

confidence: 89%

Unique Twisted Ribbons Generated by Self‐Assembly of Oligo(p‐phenylene ethylene) Bearing Dimeric Bile Acid Pendant Groups

Wang

et al. 2009

Chemistry A European J

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Section: Ortho-phenylenethinylen-makrocyclenunclassified

“…[50][51][52] Die amphiphile Verbindung 60 a mit polaren Ethylenoxidseitenketten lagert sich bei der Einwirkung von Wasser auf eine CHCl 3 -Lçsung spontan zu Vesikeln zusammen (Abbildung 9). [50] Die Selbstorganisation der scheibenfçrmigen Verbindung 60 b mit drei Carboxylgruppen in der Peripherie zu sphärischen Vesikeln repräsentiert eine neue molekulare Architektur für die Versikelbildung. [51] Interessanterweise zeigte ein Einkristall von 60 b·3 DMSO bei einer zeitaufgelçsten Messung der Mikrowellenleitfähigkeit nach Flash-Photolyse (flash photolysis time-resolved microwave conductivity, FP-TRMC) eine signifikante anisotrope Ladungsträgerbeweglichkeit (S m = 1.…”

Section: Ortho-phenylenethinylen-makrocyclenunclassified

Konjugierte Makrocyclen: Konzepte und Anwendungen

2011

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Eines der wichtigsten Ziele in den Materialwissenschaften, der Chemie und der Physik ist die Herstellung von großen konjugierten Makrocyclen genau definierter Form, da solche Moleküle nicht nur theoretisch und experimentell interessant sind, sondern auch potenzielle Anwendungen in der Nanotechnologie haben. Vollständig ungesättigte Makrocyclen werden als Modelle für vollständig konjugierte π‐Systeme mit Hohlräumen herangezogen. Solche konjugierten π‐Systeme zeigen aufgrund ihrer cyclischen Konjugation ein ungewöhnliches optisches und magnetisches Verhalten. Makrocyclen haben nach innen und nach außen gerichtete Bindungsstellen, und eine positionsspezifische Substitution an beiden oder nur einer der beiden Bindungsstellen kann attraktive Strukturen zugänglich machen. Von besonderer Bedeutung sind ein‐, zwei‐ und dreidimensionale supramolekulare Nanostrukturen. Um die Bildung dieser Strukturen kontrollieren zu können, bietet sich die Bottom‐Up‐Synthese ausgehend von π‐expandierten Makrocyclen an. Zahlreiche formstabile π‐konjugierte Makrocyclen wurden synthetisiert, davon aber nur eine begrenzte Zahl an nanoskaligen Vertretern. In diesem Aufsatz konzentrieren wir uns auf nanometergroße π‐konjugierte Makrocyclen (>1 nm Durchmesser) sowie Riesenmakrocyclen (>2 nm Durchmesser) und fassen deren Synthesen und Eigenschaften zusammen.

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“…Keywords: charge-carrier mobility · dehydroannulenes · fluorescence · pi interactions · solid-state structures some well-designed supramolecular architectures based on [n]DBA have been reported in crystals, [6] in liquid crystals, [7] in gels, [5f,g] in vesicles, [8] and on surfaces. [9] However, revealing the relationship between the superstructures and physical properties, such as optical, electrical, and electronic properties, and the development of novel functional materials based on [n]DBAs still remain as challenges.…”

Section: Introductionmentioning

confidence: 99%

Superstructure‐Dependent Optical and Electrical Properties of an Unusual Face‐to‐Face, π‐Stacked, One‐Dimensional Assembly of Dehydrobenzo[12]annulene in the Crystalline State

Hisaki

Sakamoto

Shigemitsu

et al. 2008

Chemistry A European J

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To develop a novel pi-conjugated molecule-based supramolecular assembly, we designed and synthesized trisdehydrotribenzo[12]annulene ([12]DBA) derivative 2 with three carboxyl groups at the periphery. Recrystallization of 2 from DMSO gave a crystal of the solvate 23 DMSO. Crystallographic analysis revealed, to our surprise, that a face-to-face pi-stacked one-dimensional (1D) assembly of 2 was achieved and that the DMSO molecule played a significant role as a "structure-dominant element" in the crystal. This is the first example of [12]DBA to stack completely orthogonal to the columnar axis. To reveal its superstructure-dependent optical and electrical properties, 2 and its parent molecule 1, which crystallizes in a herringbone fashion, were subjected to fluorescence spectroscopic analysis and charge-carrier mobility measurements in crystalline states. The 1D stacked structure of 2 provides a red-shifted, broadened, weakened fluorescence profile (lambda(max) = 545 nm, phi(F) = 0.01), compared to 1 (lambda(max) = 491 nm, phi(F) = 0.12), due to strong interactions between the p orbitals of the stacked molecules. The charge-carrier mobility of the single crystal of 23 DMSO, as well as 1, was determined by flash photolysis time-resolved microwave conductivity (FP-TRMC) measurements. The single crystal of 23 DMSO revealed significantly-anisotropic charge mobility (sigma(mu) = 1.5x10(-1) cm(2) V(-1) s(-1)) along the columnar axis (crystallographic c axis). This value is 12 times larger than that along the orthogonal axis (the a axis).

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Self‐Assembled Vesicles from an Amphiphilic ortho‐Phenylene Ethynylene Macrocycle

Cited by 43 publications

References 68 publications

Unique Twisted Ribbons Generated by Self‐Assembly of Oligo(p‐phenylene ethylene) Bearing Dimeric Bile Acid Pendant Groups

Unique Twisted Ribbons Generated by Self‐Assembly of Oligo(p‐phenylene ethylene) Bearing Dimeric Bile Acid Pendant Groups

Konjugierte Makrocyclen: Konzepte und Anwendungen

Superstructure‐Dependent Optical and Electrical Properties of an Unusual Face‐to‐Face, π‐Stacked, One‐Dimensional Assembly of Dehydrobenzo[12]annulene in the Crystalline State

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