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3 article(s) from Pithan, Phil M

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

Phil M. Pithan,
Sören Steup and
Heiko Ihmels

Beilstein J. Org. Chem. 2020, 16, 904–916, doi:10.3762/bjoc.16.82

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Scheme 1: Photo- or cation-induced ring-opening reaction of spirooxazine 1a^SO; Mⁿ⁺ = Pb²⁺, La³⁺, Eu³⁺, Tb³⁺ [17].

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Scheme 2: Synthesis of the spirooxazine–quinolizinium conjugates 3a and 3b.

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Figure 1: Colors of the solutions resulting from the addition of metal ions (c = 50 µM) to derivative 3a (c =...

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Figure 2: Spectrophotometric titration of 3a (A) and 3b (B) (c = 20 µM) with Cu(BF₄)₂ (c = 2.44 mM) in MeCN. ...

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Figure 3: Absorption (A) and fluorescence spectrum (B) of 3a in MeCN (c = 5 µM) in the absence (black) and in...

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Figure 4: Emission colors of solutions resulting from the addition of metal ions (c = 50 µM) to derivative 3a...

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Scheme 3: Cu²⁺-induced formation of the oxazole derivatives 4a and 4b.

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Figure 5: ¹H NMR spectra (600 MHz, 6.4–9.4 ppm) of 3a (c = 2.0 mM) in the absence (A) and in the presence (B–...

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Figure 6: Spectral changes of 3a (c = 20 µM) upon the addition of Cu²⁺ (A) and Fe³⁺ (B) (c_M+ = 60 µM) in MeCN...

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Scheme 4: Proposed mechanism for the formation of the oxazole derivatives 4a and 4b (cf. Scheme 3); Mⁿ⁺ = Cu²⁺, Fe³⁺,...

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Published 05 May 2020

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

Jonas Becher,
Daria V. Berdnikova,
Darinka Dzubiel,
Heiko Ihmels and
Phil M. Pithan

Beilstein J. Org. Chem. 2017, 13, 203–212, doi:10.3762/bjoc.13.23

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Figure 1: Structures of quinolizinium derivatives 1a–c and 2.

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Scheme 1: Synthesis of 3-hydroxynaphtho[1,2-b]quinolizinium bromide (2).

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Figure 2: Absorption (A, c = 100 µM) and normalized emission spectra (B, c = 10 µM or Abs. = 0.1 at λ_ex) of d...

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Figure 3: Photometric (A) and fluorimetric (B) acid–base titration (λ_ex = 380 nm) of naphthoquinolizinium 2 (c...

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Figure 4: Absorption spectra of 2 (c = 100 µM) in MeOH (A) and MeCN (B). Black lines: without additive, red: ...

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Figure 5: Normalized emission spectra of 2 (c = 10 µM) in MeOH (A, λ_ex = 400 nm) and MeCN (B, λ_ex = 398 nm). ...

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Figure 6: Photometric titration of CB[7] (c = 0.45 mM) to 2 (c = 15 µM) in BPE buffer (with 10% v/v DMSO) at ...

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Figure 7: Photometric (A) and fluorimetric (B) acid–base titration (λ_ex = 380 nm) of 2 (c = 15 µM) in the pre...

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Scheme 2: Acid–base equilibrium of hydroxynaphthoquinolizinium 2.

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Figure 8: Structures of quinolizinium derivatives 6–8.

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Published 01 Feb 2017

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Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives

Phil M. Pithan,
David Decker,
Manlio Sutero Sardo,
Giampietro Viola and
Heiko Ihmels

Beilstein J. Org. Chem. 2016, 12, 854–862, doi:10.3762/bjoc.12.84

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Figure 1: Structures of biaryl-type benzo[b]quinolizinium derivatives 1a–f.

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Scheme 1: Synthesis of 3-bromonaphtho[1,2-b]quinolizinium bromide (4).

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Scheme 2: Synthesis of the 3-aryl-substituted naphtho[1,2-b]quinolizinium derivatives 6a–e.

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Figure 2: Absorption spectra of derivatives 6a (A), 6c (B), 6d (C), and 6e (D); c = 20 µM; solvents: H₂O (red...

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Figure 3: Normalized emission spectra of derivatives 6a (A), 6c (B), 6d (C) and 6e (D) (Abs. = 0.10 at excita...

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Figure 4: Fluorescence colors of derivative 6e in various solvents; λ_ex = 366 nm. 1: CHCl₃, 2: H₂O, 3: CH₂Cl₂...

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Scheme 3: Intramolecular charge shift upon excitation in derivatives 6b–e (see Scheme 2 for assignment of substituent...

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Figure 5: Plot of the emission energy of 6e versus the solvent polarity parameter E_T(30).

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Scheme 4: State diagram of the photoexcitation and deactivation pathways of 3-aryl-naphthoquinolizinium deriv...

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Figure 6: Structures of biaryl derivatives 7a–c.

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Published 02 May 2016

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