Synthesis and Properties of Acridine and Acridinium Dye Functionalized Bis(terpyridine) Ruthenium(II) Complexes

Eberhard, Jens; Peuntinger, Katrin; Fröhlich, Roland; Guldi, Dirk M.; Mattay, Jochen

doi:10.1002/ejoc.201800257

Cited by 17 publications

(12 citation statements)

References 124 publications

(155 reference statements)

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“…Acridinium derivatives have two main bands in their absorption spectra, as shown in Figure . It is known that a very narrow absorption band at about 360 nm is attributed to the S 0 –S 2 transition and a broad absorption band at about 450 nm is attributed to the S 0 –S 1 transition. , To discuss the S 0 –S 1 transition, the integral values of the extinction coefficient at 380–550 nm are summarized in Table . The integral values of the extinction coefficient of Acr on the clay surface were larger than those in water (Table ) in most cases, indicating an increase in the transition probability, namely, the Franck–Condon factor, when Acr is adsorbed on the clay surface.…”

Section: Resultsmentioning

confidence: 99%

Effects of the Surface Charge Density of Clay Minerals on Surface-Fixation Induced Emission of Acridinium Derivatives

et al. 2021

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Surface-fixation induced emission is a fluorescence enhancement phenomenon, which is expressed when dye molecules satisfy a specific adsorption condition on the anionic clay surface. The photophysical behaviors of two types of cationic acridinium derivatives [10-methylacridinium perchlorate (Acr + ) and 10-methyl-9-phenylacridinium perchlorate (PhAcr + )] on the synthetic saponites with different anionic charge densities were investigated. Under the suitable conditions, the fluorescence quantum yield (Φ f ) of PhAcr + was enhanced 22.3 times by the complex formation with saponite compared to that in water without saponite. As the inter-negative charge distance of saponite increased from 1.04 to 1.54 nm, the Φ f of PhAcr + increased 1.25 times. In addition, the increase in the negative charge distance caused the increase in the integral value of the extinction coefficient and the radiative deactivation rate constant ( k f ) and the decrease in the nonradiative deactivation rate constant. It should be noted that the 2.3 times increase in k f is the highest among the reported values for the effect of clay. From these results, it was concluded that the photophysical properties of dyes can be modulated by changing the charge density of clay minerals.

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Section: Resultsmentioning

confidence: 99%

Effects of the Surface Charge Density of Clay Minerals on Surface-Fixation Induced Emission of Acridinium Derivatives

et al. 2021

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“…N-Methylacridinium iodide (NMAI) was synthesized according to the literature procedure. 33 Briefly, a 100 mL oven-dried roundbottom flask was charged with a stir bar. A 5.0 g portion of acridine (27.6 mmol) was dissolved in 20 mL of DMF and was heated to 35 °C for 10 min.…”

Section: ■ Methodsmentioning

confidence: 99%

“…N -Methylacridinium iodide (NMAI) was synthesized according to the literature procedure . Briefly, a 100 mL oven-dried round-bottom flask was charged with a stir bar.…”

Section: Methodsmentioning

confidence: 99%

Triggered Transience of Plastic Materials by a Single Electron Transfer Mechanism

et al. 2020

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Transient polymers rapidly and controllably depolymerize in response to a specific trigger, typically by a chain-end unzipping mechanism. Triggers, such as heat, light, and chemical stimuli, are generally dependent on the chemistry of the polymer backbone or end groups. Single electron transfer (SET), in contrast to other triggering mechanisms, is achievable by various means including chemical, electrochemical, and photochemical oxidation or reduction. Here, we identify SET and subsequent mesolytic cleavage as the major thermal triggering mechanism of cyclic poly(phthalaldehyde) (cPPA) depolymerization. Multimodal SET triggering is demonstrated by both chemical and photoredox-triggered depolymerization of cPPA. Redox-active small molecules (p-chloranil and 1,3,5-trimethoxybenzene) were used to tune the depolymerization onset temperature of cPPA over the range 105−135 °C. Extending this mechanism to photoredox catalysis, N-methylacridinium hexafluorophosphate (NMAPF 6 ) was used to photochemically degrade cPPA in solution and thin films. Finally, we fabricated photodegradable cPPA monoliths with a storage modulus of 1.8 GPa and demonstrated complete depolymerization within 25 min of sunlight exposure. Sunlight-triggered depolymerization of cPPA is demonstrated and potentially useful for the manufacture of transient devices that vanish leaving little or no trace. Most importantly, this new mechanism is likely to inspire other SET-triggered transient polymers, whose development may address the ongoing crisis of plastic pollution.

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“…1,2 Basic research concerning acridinium dyes was mostly aimed at characterization of charge-transfer processes in those compounds during electron excitation. 3−11 From the practical point of view, significant efforts have been devoted to utilizing acridine dyes as sensor materials for detection of anions 12−15 as well as for biolabeling purposes. 16−18 There is also an increased interest in their use as components for the construction of organic light-emitting diodes (LEDs) 19−22 and solar cells.…”

Section: Introductionmentioning

confidence: 99%

Cationic and Betaine-Type Boronated Acridinium Dyes: Synthesis, Characterization, and Photocatalytic Activity

et al. 2019

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A series of isomeric boronated acridinium dyes were obtained by reactions of 10-(4′-octyloxyphenyl) functionalized 9(10 H )-acridanone derivative with lithiated phenylboronic azaesters followed by aromatization with perchloric acid. The effect of the position of boronic group attached at ortho, meta, and para positions of the 9-phenyl ring on the photophysical properties was investigated. Conversion to related betaine trifluoroborato-substituted compounds was successfully performed, and the effect of this structural change on UV–vis absorption and fluorescence spectroscopy characteristics was established. Furthermore, cyclic voltammetry studies revealed that electrochemical behavior of cationic versus betaine structures is different in terms of redox potential values as well as stability. The theoretical calculations revealed a different scheme for molecular excitation processes in B(OH) 2 versus BF 3 – -substituted compounds as charge transfer to acridinium core is observed from N -aryl or B -aryl moiety, respectively. Obtained compounds were active as photocatalysts in selected visible-light-promoted addition reactions to unsaturated substrates.

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Synthesis and Properties of Acridine and Acridinium Dye Functionalized Bis(terpyridine) Ruthenium(II) Complexes

Cited by 17 publications

References 124 publications

Effects of the Surface Charge Density of Clay Minerals on Surface-Fixation Induced Emission of Acridinium Derivatives

Effects of the Surface Charge Density of Clay Minerals on Surface-Fixation Induced Emission of Acridinium Derivatives

Triggered Transience of Plastic Materials by a Single Electron Transfer Mechanism

Cationic and Betaine-Type Boronated Acridinium Dyes: Synthesis, Characterization, and Photocatalytic Activity

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