Rotaxane-encapsulated cyanine dyes: enhanced fluorescence efficiency and photostability

Buston, Jonathan Ε. H.; Young, Jim; Anderson, Harry L.

doi:10.1039/b001812k

Cited by 145 publications

(83 citation statements)

References 19 publications

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“…Uns gelang die Synthese von Cyanin-Rotaxanen durch Knoevenagel-Reaktionen in wäss-rigem Medium. [66,67] Bei der Reaktion in Schema 6 entstehen die beiden [2]Rotaxan-Stereoisomere A-16&a-CD und B16&a-CD, die anschließend chromatographisch getrennt werden konnten. Die chemische Beständigkeit des Cyaninfarbstoffs ist in diesen Rotaxanen deutlich erhöht (Abschnitt 5.1).…”

Section: Cyanin-rotaxaneunclassified

“…Synthese einer trennbaren Mischung aus zwei Stereoisomeren eines Cyanin-Rotaxans. [66,67] Abbildung 7. Ausgedehnte p-Stapel von [2]Rotaxan-Molekülen in den Kristallstrukturen von 17&a-CD (a), [69] 18&a-CD (b), [70] 19&a-CD (c) und 20&a-CD (d) [71] in zwei orthogonalen Ansichten.…”

Section: Angewandte Chemieunclassified

“…Beispielsweise ist das Cyanin-Rotaxan 26&a-CD 40-mal stabiler gegen photochemische Oxidation als der freie Cyaninfarbstoff (Abbildung 20). [67] Cyanin-Rotaxane zeigen auch ein ausgeprägt reversibles Redoxverhalten, da die oxidierten und reduzierten Formen kinetisch stabil sind. Dies bestätigen die Cyclovoltammogramme der in Schema 6 abgebildeten Rotaxane 16&a-CD.…”

Section: Beständigkeit Und Chemische Reaktivität Eingeschlossener P-sunclassified

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Isolierte molekulare Drähte

2007

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In den erstaunlich unterschiedlichen Strukturen, die bisher als “isolierte molekulare Drähte” (insulated molecular wires, IMWs) beschrieben wurden, zeigt sich, wie vielfältig die Ansätze zur elektrisch‐chemischen Isolierung auf molekularer Ebene sind. Gemeinsam verdeutlichen diese Systeme die Bedeutung von Einkapselungsstrategien bei der Entwicklung optoelektronischer Materialien und organischer Halbleiter. Dieser Aufsatz beleuchtet die Synthese und die strukturelle Charakterisierung von IMWs. Struktur‐Eigenschafts‐Beziehungen sollen zudem erklären, wie eine Isolierung die Leistungsmerkmale eines molekularen Drahtes verbessern kann. Wir konzentrieren uns auf drei IMW‐Arten: Polyrotaxane, polymerumhüllte π‐Systeme und dendronisierte Polymere. Die Eigenschaften dieser Systeme werden mit denjenigen von konjugierten Polymeren verglichen, die in mesoporöse Netzwerke und Zeolithe eingefädelt sind. Der Einschluss molekularer Drähte verstärkt so unterschiedliche Eigenschaften wie Lumineszenz, elektrische Transportgrößen und die chemische Beständigkeit, sodass Anwendungen in Elektrolumineszenzdisplays, Sensoren und der photochemischen Wasserstofferzeugung denkbar werden.

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Section: Cyanin-rotaxaneunclassified

Section: Angewandte Chemieunclassified

Section: Beständigkeit Und Chemische Reaktivität Eingeschlossener P-sunclassified

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Isolierte molekulare Drähte

2007

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“…It is known that guest molecules may behave differently inside the host molecule [9][10][11][12][13][14][15]. For example, highly conjugated cyanine dyes get a boost in fluorescence response when complexed with cyclodextrins [10,11]. As most molecular properties depend on structural arrangements, it is important to learn about the structural arrangement of host-guest complexes.…”

Section: Introductionmentioning

confidence: 99%

“…Aromatic bifunctional aminothiophenols have been employed for this purpose by making a host-guest complex with β-CD [5]. It is known that guest molecules may behave differently inside the host molecule [9][10][11][12][13][14][15]. For example, highly conjugated cyanine dyes get a boost in fluorescence response when complexed with cyclodextrins [10,11].…”

Section: Introductionmentioning

confidence: 99%

Host–Guest Complex of β-Cyclodextrin and Disulfide Form of 4-Aminothiophenol

Cappadona

Daniels²,

Siddiquee

2012

Applied Sciences

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An inclusion complex of β-cyclodextrin and 4-aminothiophenol was assembled by hydrophobic interaction of the host (β-cyclodextrin) and guest (4-aminothiophenol). The complex was isolated as crystalline solid and studied by single crystal X-ray diffraction method along with NMR and IR spectroscopy. Two cyclodextrin rings each containing one disulfide form of 4-aminothiophenol were found to pair up by hydrogen bonding of the outer rim -OH groups. The phenyl disulfide moiety of 4-aminophenyl disulfide molecule was found in the core of β-cyclodextrin, while the amino functional groups were positioned to the exterior of the cyclodextrin ring. Phenyl rings of the guest molecule from each partner of the paired cyclodextrin complex were found parallel to each other, indicating possible π-π stacking interaction between them.

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Rotaxane-Encapsulation Enhances the Stability of an Azo Dye, in Solution and when Bonded to Cellulose

Craig

Hutchings²,

Claridge

et al. 2001

Angew. Chem.

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The groups of Cram and Warmuth have shown that exotic high-energy intermediates such as cyclobutadiene, orthobenzyne, and cycloheptatetraene can be stabilized by encapsulation inside calixarene-based cages. [1] These results inspired us to attempt to encapsulate and stabilize more mundane species such as dyes [2] and conjugated polymers [3] by synthesizing rotaxanes [4] in which the reactive p system of the dye or polymer is protected inside the cavity of a macrocycle. We have previously reported the synthesis of azo dye rotaxanes; [2a±c, 5] however, two key questions remained unanswered: a) Does encapsulation improve the longevity of the azo chromophore? b) Does encapsulation detrimentally prevent the dye from binding to surfaces? Here we address these issues by reporting an efficient synthesis of a Figure 4. A TEM photograph and an SAED pattern of a cross section of a layer overgrown on a sodalite {111} substrate. a) The substrate is sodalite {111} prepared by mechanical polishing. The cancrinite crystals grow perpendicular to the sodalite {111} substrate. b) An SAED pattern recorded along the sodalite [12 Å 5 Å ] zone axis. Spots due to cancrinite and sodalite are observed and indexed. c) A composite electron-diffraction simulation along the sodalite [12 Å 5 Å ]/cancrinite [2 Å 112] zone axis. The spots resulting from superposition of diffracted beams from sodalite and cancrinite crystal planes are circled.

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Rotaxane-encapsulated cyanine dyes: enhanced fluorescence efficiency and photostability

Abstract: Two isomers of a cyanine dye a-cyclodextrin rotaxane have been synthesised in aqueous solution, and structurally characterised by 2D NMR spectroscopy; they exhibit enhanced fluorescence and photostability, compared with the free dye.

Cited by 145 publications

References 19 publications

Isolierte molekulare Drähte

Isolierte molekulare Drähte

Host–Guest Complex of β-Cyclodextrin and Disulfide Form of 4-Aminothiophenol

Rotaxane-Encapsulation Enhances the Stability of an Azo Dye, in Solution and when Bonded to Cellulose

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