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1 article(s) from Steup, Sören

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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Graphical Abstract

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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