Optimization of neutrocyanine chromophores based on five-membered heterocycles for photorefractive applications

Würthner, Frank; Thalacker, Christoph; Matschiner, Ralf; Lukaszuk, Katarzyna; Wortmann, Rüdiger

doi:10.1039/a804168g

Cited by 59 publications

(53 citation statements)

References 14 publications

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“…For the same reason, staining capability for PO of ''free bases'' of dimethylaminostyryl dyes is generally low (e.g. 1a =[ VIII), especially in comparison with their phenol-analogues (here VIII, Krieg et al 2007 stabilization energies of merocyanine dyes (Beckmann et al 1999;Marder et al 1994;Wortmann et al 1998;Würthner et al 1998; cyclic cyanines: Formula 9: X, Y = S, O, NR, CH = CH; substrates here: phenols: D = OH, X = CH = CH; amines: D = NR 2 , X = CH = CH).…”

Section: Synthesis Of Dyesmentioning

confidence: 99%

N,N-Dialkylaminostyryl dyes: specific and highly fluorescent substrates of peroxidase and their application in histochemistry

et al. 2007

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Fluorescent labeling of immuno-bound or endogenous peroxidase (PO) activity has been achieved to date by means of phenol derivatives with a low substitution degree. Here it is demonstrated that N,N-dialkylamino-styryl dyes can also act as fluorescent substrates of PO. They undergo enzymatically cross-linking reactions to surrounding cell constituents in an analogous manner thus permitting highly fluorescent and permanent labeling. This approach is narrowly related to the catalyzed reporter deposition (CARD) technique based on tyramine conjugates and the recently described catalytic cross-linking approach of hydroxystyryl derivatives. The substitution patterns for optimal cross-linking capability and the spectral properties of obtained specific reaction products were studied using an iterative semi-empirical approach. The best staining performance is achieved with N,N-dimethylaminoaryl derivatives. Their N,N-dialkyl homologues as well as the primary aryl amine pendants failed as PO substrates. Due to their basic character, novel substrates occasionally tend to unspecific interactions (staining nuclei, mast cells, or keratin). Centering this side specificity and repressing the staining capability of PO was achieved by chemical modification of the respective dye leading to new specific probes for keratin and cytoplasmatic RNA. In conclusion, catalytic cross-linking of heterocyclic 4-N,N-dimethylamino-styryl dyes represents a promising approach for the permanent fluorescent staining of PO in fixed cells and tissues, complementing the CARD technique. In contrast to CARD-related approaches, new substrates are characterized by a broad excitation and emission range of fluorescence and the outstanding spatial resolution of specific fluorescence signaling known so far from their 4-hydroxystyryl analogues. They currently represent the smallest fluorescent substrates of PO. Histochemical and immuno-histochemical applications share several outstanding features: High detection sensitivity, spatial resolution of fluorescence signaling, and photo stability. 4-N,N-dimethylamino-styryl substrates are compatible with their phenol and phenol-ester analogues. Their combination facilitates the trichromatic immuno-histochemical demonstration of three different targets simultaneously at one excitation wavelength in a conventional epi-fluorescence microscope.

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Section: Synthesis Of Dyesmentioning

confidence: 99%

N,N-Dialkylaminostyryl dyes: specific and highly fluorescent substrates of peroxidase and their application in histochemistry

et al. 2007

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“…Wortmann und Mitarbeiter [7][8][9] haben den nach Gleichung (32) zoukas et al [6] verwenden in Gleichung (30) sin q/2 anstelle von c und definieren den "Mischparameter" MIX als Àcos q, was (2c 2 À1) in Gleichung (33) entspricht. Marder und Mitarbeiter [2][3][4][5] führten den Parameter BLA für die Bindungslängen-Alternanz in linearen D-p-A-Ketten ein.…”

Section: Angewandte Chemieunclassified

“…Eine Reihe von Parametern wie BLA, [2][3][4][5] MIX [6] oder c 2 [7][8][9] wurde zur Quantifizierung zwitterionischer Grenzstrukturen vorgeschlagen, die in Abschnitt 5 diskutiert werden sollen. Es sei allerdings hier schon vermerkt, dass das "Gewicht" der jeweiligen Resonanzstrukturen von externen Faktoren wie dem Lösungsmittel oder einem elektrischen Feld abhängt.…”

Section: Introductionunclassified

Konjugierte Oligomere mit terminaler Donor‐Acceptor‐Substitution

Meier

2005

Angewandte Chemie

103

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Konjugierte Oligomere sind in theoretischer, präparativer und materialwissenschaftlicher Hinsicht eine prominente Substanzklasse. Die Push‐pull‐Substitution durch einen Elektronendonor an einem Ende und einen Elektronenacceptor am anderen Ende verleiht den Verbindungen D‐π‐A besondere optische und elektronische Eigenschaften. Der vorliegende Aufsatz schildert die grundsätzlichen Strategien zur Synthese solcher Oligomerenreihen mit n Wiederholungseinheiten (n=1, 2, 3, 4, …︁) und die für ihre linearen und nichtlinearen optischen Eigenschaften (Absorption, Frequenzverdoppelung und ‐verdreifachung) geltenden Gesetzmäßigkeiten. Aus den chemischen, physikalischen und theoretischen Aspekten der push‐pull‐substituierten konjugierten Oligomere soll sich ein interdisziplinäres Bild dieser Verbindungsklasse zusammenfügen.

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“…Since this effect was discovered, it has been fully utilized in preparing PR composite materials. Two major design strategies have been developed: 1) lowering T g to enhance the mobility of the chromophore 14,36) and 2) using chromophores with large polarizability anisotropy (Da), large transition dipole l ag , minimal dipole moment change between ground and excited state and minimal b 0 value [38][39][40] . The second strategy is motivated by the consideration of a new figure-of-merit expression derived from the reorientation enhancement model, where a 0 and b 0 are two-level approximations of the first order and second order polarizabilities of the chromophore 41) .…”

Section: Polymeric Composite Pr Materialsmentioning

confidence: 99%

“…The steady-state PR performance was found to be independent of the chromophore's isomer ratio. A similar approach was utilized to prepare a PR composite based on isomeric mixtures of the chromophore NPADVBB, whereas NPADVBB is a mixture of four isomers, with vinyl groups in positions (3,39), (3,49), (4,39) and (4,49) 55) . Although it was claimed that this composite exhibited an improved shell lifetime by two orders of magnitude, the gain coefficient achieved was significantly smaller than that obtained for a similar DMNPAAbased sample.…”

Section: Polymeric Composite Pr Materialsmentioning

confidence: 99%

Development of fully functionalized photorefractive polymers

Wang

2000

Macromol. Rapid Commun.

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In this article, we review recent progress in the area of photorefractive polymers. Photorefractive (PR) polymers are multifunctional materials which combine photoconductivity and electro‐optic response to show a new phenomenon: light‐induced reversible modulation of the refractive index. Because of their multifunctional features, design, synthesis and preparation of these materials exhibiting high performance is an intellectual challenge. Moreover, numerous applications of photorefractive materials in optical devices have been established using inorganic materials. Utilizing the unique features of organic polymeric materials to prepare useful devices is an engineering challenge. In the past several years, research in this area has gained momentum because numerous new materials which possess better characteristic photorefractive parameters than their inorganic counterparts have been synthesized. Several interesting devices have been presented. Two different approaches have been developed to synthesize and prepare PR polymers, namely composite materials and fully functionalized polymers. Both approaches have had success in identifying new materials and in gaining understanding of the design principles of better materials. This paper discusses these aspects and gives a prospective view about this field.

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Optimization of neutrocyanine chromophores based on five-membered heterocycles for photorefractive applications

Cited by 59 publications

References 14 publications

N,N-Dialkylaminostyryl dyes: specific and highly fluorescent substrates of peroxidase and their application in histochemistry

N,N-Dialkylaminostyryl dyes: specific and highly fluorescent substrates of peroxidase and their application in histochemistry

Konjugierte Oligomere mit terminaler Donor‐Acceptor‐Substitution

Development of fully functionalized photorefractive polymers

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