The benzo[b]quinolizinium ion as a water-soluble platform for the fluorimetric detection of biologically relevant analytes

Granzhan, Anton; Ihmels, Heiko; Tian, Maoqun

doi:10.3998/ark.5550190.p009.339

Cited by 37 publications

(23 citation statements)

References 115 publications

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“…Therefore, it may be concluded that an annelated quinolizinium fluorophore with a biaryl structure is generally fluorosolvatochromic as long as the aryl substituent has the propensity to form a stabilized radical cation upon a photoinduced charge shift. This observation emphasizes the utility of the quinolizinium ion as a key element in fluorescent probes 10 and should be relevant for the development of functional solvatochromic probes, because the size and shape of the annelated quinolizinium unit may be simply adapted to a particular application without loss of fluorosolvatochromic properties.…”

Section: Discussionmentioning

confidence: 75%

“…7,8 In particular, the emission properties of these compounds are often highly sensitive to the surrounding medium so that they can be employed as solvatochromic probes in fluorescence sensing and imaging. 9 In this context, we and others have established benzo-annelated quinolizinium ions as versatile units in water-soluble fluorescent probes, 10 for example for the fluorimetric detection of pH, metal cations, or DNA. [11][12][13][14][15][16][17][18][19] In addition, we have demonstrated that biaryl-type quinolizinium derivatives 1a-d and 2a-c (Figure 1), that carry either a donor-substituted phenyl substituent or an electron-rich polycyclic aryl substituent, exhibit a pronounced fluorosolvatochromic behavior, i.e., they cover a large range of emission maxima in different solvents.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of fluorosolvatochromic phenanthrenyl-substituted benzoquinolizinium derivatives

Ihmels¹,

Pithan²,

Schwan³

2020

Arkivoc

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The biaryl derivatives 8-(phenanthren-9-yl)benzo[c]quinolizinium and 9-(phenanthren-9-yl)benzo [b]quinolizinium were synthesized by a Suzuki-Miyaura coupling, and their steady-state absorption and emission properties were investigated. Whereas the absorption properties are essentially independent of the solvent properties, these compounds show a pronounced fluorosolvatochromism. Namely, they exhibit their lowestenergy maximum in aprotic, polar solvents and significantly blue-shifted emission bands in polar protic solvents. Notably, comparison of three different phenanthrenyl-substituted quinolizinium derivatives revealed that these fluorosolvatochromic properties are essentially independent of the annelation pattern of the quinolizinium unit, given that the aryl substituent has the propensity to form a sufficiently stabilized radical cation upon a photoinduced charge shift in the biaryl derivative.

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Section: Discussionmentioning

confidence: 75%

Section: Introductionmentioning

confidence: 99%

Synthesis of fluorosolvatochromic phenanthrenyl-substituted benzoquinolizinium derivatives

Ihmels¹,

Pithan²,

Schwan³

2020

Arkivoc

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“…With this result we demonstrated that in general the acidic functionality as well as the photophysical properties of hydroxyquinolizinium derivatives may be modulated by supramolecular interactions. Considering the ability of this class of compounds to operate as DNA-binding ligands [56] or water-soluble chemosensors [57], we anticipate that the combination of these properties with the potential for modulation by host–guest assembly may widen their versatility as functional dyes.…”

Section: Resultsmentioning

confidence: 99%

Interactions between photoacidic 3-hydroxynaphtho[1,2-b]quinolizinium and cucurbit[7]uril: Influence on acidity in the ground and excited state

Becher

Berdnikova

Dzubiel

et al. 2017

Beilstein J. Org. Chem.

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3-Hydroxynaphtho[1,2-b]quinolizinium was synthesized by cyclodehydration route and its optical properties in different media were investigated. The absorption and emission spectra of this compound depend on the pH of the solution. Thus, at higher pH values the deprotonation yields a merocyanine-type dye that exhibits significantly red-shifted absorption bands and causes a dual emisson, i.e., a combination of emission bands of the hydroxyquinolizinium and its deprotonated form. Whereas this compound is a weak acid in the ground state (pK a = 7.9), it has a strongly increased acidity in the excited state (pK a * = 0.4). As a result, the blue-shifted fluorescence of the hydroxyquinolizinium becomes dominant only under strongly acidic conditions. In addition, it is shown that 3-hydroxynaphtho[1,2-b]quinolizinium binds to cucurbit[7]uril (CB[7]) with moderate affinity (K b = 1.8 × 104 M−1, pH 5) and that the pK a and pK a * values of this ligand increase by about two to three orders of magnitude, respectively, when bound to CB[7].

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“…In this context, we were interested in the effect of a positively charged arylvinyl substituent on the photochromic properties of the spironaphthoxazine. For this purpose, we chose the quinolizinium ion as the cationic aryl substituent because it has been shown that derivatives thereof have a great potential to serve as functional units in DNA-binding ligands [54], fluorescent dyes and chemosensors [55][56][57][58][59]. Furthermore, we have already demonstrated that styryl-substituted quinolizinium derivatives exhibit ideal photophysical and DNA-binding properties to be used as DNA-sensitive fluorescent probes in cell imaging [60][61][62] or as photoswitchable DNA ligands [63].…”

Section: Introductionmentioning

confidence: 99%

Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates

Pithan¹,

Ihmels²

2020

Beilstein J. Org. Chem.

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Two new spiroindolinonaphthoxazine derivatives with an electron-accepting styrylquinolizinium or styrylcoralyne unit, respectively, were synthesized, and the influence of such an arylvinyl substituent on the chemical and photochemical properties of the compounds was investigated. Specifically, these spirooxazines turned out to be resistant towards the photoinduced merocyanine formation, and the irradiation with light mainly led to photodegradation of the substrates. However, it was shown by colorimetric and fluorimetric screening assays as well as by detailed NMR spectroscopic and mass spectrometric studies that the addition of particular metal ions (Cu2+, Fe3+, and to a certain extent Hg2+) initially induced a ring-opening reaction that was irreversibly followed by a fast ring closure–deprotonation–oxidation sequence to give styryl-substituted naphthoxazole derivatives as the products quantitatively. For the quinolizinium-substituted spirooxazine derivative, the formation of the respective oxidation product caused the development of a broad absorption band between 425 nm and 500 nm and a new emission band at λfl = 628 nm, so that it may be employed as a selective chemosensor or chemodosimeter for the colorimetric and fluorimetric detection of Cu2+ and Fe3+.

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The benzo[b]quinolizinium ion as a water-soluble platform for the fluorimetric detection of biologically relevant analytes

Cited by 37 publications

References 115 publications

Synthesis of fluorosolvatochromic phenanthrenyl-substituted benzoquinolizinium derivatives

Synthesis of fluorosolvatochromic phenanthrenyl-substituted benzoquinolizinium derivatives

Interactions between photoacidic 3-hydroxynaphtho[1,2-b]quinolizinium and cucurbit[7]uril: Influence on acidity in the ground and excited state

Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates

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