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Search for "indigoid dyes" in Full Text gives 1 result(s) in Beilstein Journal of Organic Chemistry.

Photochromic derivatives of indigo: historical overview of development, challenges and applications

Gökhan Kaplan,
Zeynel Seferoğlu and
Daria V. Berdnikova

Beilstein J. Org. Chem. 2024, 20, 228–242, doi:10.3762/bjoc.20.23

of prospective applications of indigo photoswitches. Keywords: indigoid dyes; photochemistry; photophysics; photoswitching; E–Z isomerization; Review Historical milestones in the development of photochromic indigo derivatives 1954: first reported photochromic indigo derivative – N,N'-diacetylindigo

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Graphical Abstract

Figure 1: Precursors used in the synthesis of indigo [4].

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Figure 2: a) Intramolecular (a = 2.26 Å) and intermolecular (b = 2.11 Å) hydrogen bonds in indigo, b) crystal...

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Figure 3: Bond length in the indigo molecule obtained from the single crystal X-ray analysis [12], the typical bo...

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Figure 4: The structure of the indigo chromophore (H-chromophore, highlighted in blue), asterisk indicates th...

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Figure 5: Influence of substituents in the benzene rings on the color of indigo derivatives.

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Figure 6: a) E–Z photoisomerization of indigo and b) photoinduced proton transfer in the excited state, aster...

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Figure 7: Structures of indigo derivatives discussed in this review.

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Figure 8: Photoswitching of N,N'-diacetylindigo (9a) in CCl₄ (c = 17.1 µM; cell length = 5.0 cm) irradiated w...

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Figure 9: Photoisomerization of compound 18c upon irradiation with red light and schematic representation of ...

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Figure 10: Schematic representation of indigo-type (left) and amide-type (right) resonances in N,N'-acetylindi...

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Figure 11: Suggested intermediates for the double bond cleavage for the thermal relaxation of N,N'-diacylindig...

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Figure 12: Zwitterionic resonance structures of Z-indigo.

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Figure 13: Photos of crystalline N,N'-di(Boc)indigo 17a its solutions in 1) DMSO, 2) DMF, 3) N-methyl-2-pyrrol...

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Figure 14: Structural isomers of indigo.

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Figure 15: Photochromism of indirubin derivatives and supramolecular complexation of the E-isomers with Schrei...

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Figure 16: Photoisomerization of the protonated isoindigo.

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Review

Published 07 Feb 2024

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